Hindawi Publishing CorporationISRN Organic ChemistryVolume 2013 Article ID 526173 6 pageshttpdxdoiorg1011552013526173

Research ArticleDABCO Catalyzed Synthesis of Xanthene Derivatives inAqueous Media

Pradeep Paliwal Srinivasa Rao Jetti Anjna Bhatewara Tanuja Kadre and Shubha Jain

Laboratory of Heterocycles School of Studies in Chemistry amp Biochemistry Vikram University Ujjain Madhya Pradesh 456010 India

Correspondence should be addressed to Shubha Jain drshubhajain479gmailcom

Received 25 January 2013 Accepted 14 February 2013

Academic Editors V P Kukhar G Li J C Menendez and Z Wimmer

Copyright copy 2013 Pradeep Paliwal et alThis is an open access article distributed under the Creative CommonsAttribution Licensewhich permits unrestricted use distribution and reproduction in any medium provided the original work is properly cited

The reaction of 55-dimethylcyclohexane-13-dione with various heteroarylaldehydes afforded the corresponding heteroarylsubstituted xanthene derivatives 1(andashf) The reaction proceeds via the initial Knoevenagel subsequent Michael and finalheterocyclization reactions using 14-diazabicyclo[222]octane (DABCO) as a catalyst in aqueousmediaThe synthesized heteroarylsubstituted xanthenes 1(andashf) reactedwithmalononitrile to obtain different alkylidenes 2(andashf) Short reaction time environmentallyfriendly procedure avoiding of cumbersome apparatus and excellent yields are themain advantages of this procedure whichmakesit more economic than the other conventional methods

1 Introduction

In the past few decades the synthesis of new heterocycliccompounds has been a subject of great interest due totheir wide applicability The importance of multicomponentreactions in organic synthesis has been recognized andconsiderable efforts have been focused on the design anddevelopment of one-pot procedures for the generation oflibraries of heterocyclic compounds [1 2] Multicomponentreactions (MCRs) have emerged as an important tool forbuilding of diverse and complex organic molecules throughcarbon-carbon and carbon-heteroatombond formations tak-ing place in tandemmanner [3] Particularly in the last threedecades a number of three- and four-component reactionshave been developed [4ndash6]

Xanthene derivatives are very important heterocycliccompounds and have been widely used as dyes [7] andfluorescent materials for visualization of biomolecules and inlaser technologies [8] They have also been reported for theiragricultural bactericide activity [9] and anti-inflammatory[10] and antiviral activity [11] These compounds are alsoutilized as antagonists for paralyzing action of zoxazolamineand in photodynamic therapy [12] Due to their wide rangeof applications these compounds have received a great dealof attention in connection with their synthesis A widevariety of methods for the preparation of the xanthenes have

been reported [13ndash19] However many of these methods areassociated with several shortcomings such as long reactiontimes (16 h to 5 days) expensive reagents harsh conditionslow product yields and use of toxic organic solvents Diazabi-cyclo[222]octane (DABCO) is an inexpensive nontoxic andcommercially available catalyst that can be used in laboratorywithout special precautions [20ndash22] But it has not been usedas a catalyst in xanthene synthesis only a few reports aretherein the literature [23ndash25] This prompted us to developa new synthetic method for heteroaryl substituted xanthenesusing DABCO as a catalyst (see Scheme 1)

With our continued interest in the synthesis of het-erocyclic systems [26] and application of DABCO as acatalyst in organic synthesis [27] herein we wish to reporta facile condensation of heteroarylaldehyde 551015840-dimethyl-13-cyclohexanedione (dimedone) in the presence of cat-alytic amount of DABCO to produce a variety of 18-dioxo-octahydroxanthenes derivatives 1(andashf) (Scheme 2)

2 Results and Discussion

In order to optimize the reaction conditions the synthesisof compound 1d was used as a model reaction Therefore amixture of 3-methyl thienaldehyde (1 mmol) 55-dimethylcyclohexane-13-dione (2 mmol) in H

2O was refluxed for

2 ISRN Organic Chemistry

O

O

COOHAzido analogue

O

O

O

Rhodamine 123

NH2H2

N3

N

H3C

+

Scheme 1

Table 1 Influence of the amounts of DABCO on the synthesis of 1dat reflux temperaturea

Entry Catalyst Amount of catalyst Time (min) Yieldb ()(mmol)

1 None mdash 80 Trace2 DABCO 1 70 673 DABCO 2 60 744 DABCO 3 50 825 DABCO 5 40 896 DABCO 10 30 967 DABCO 15 30 96aReaction conditions 3-methyl thienaldehyde (1mmol) dimedone (2mmol)in water (20mL) under reflux temperature bIsolated yields

an appropriate time as indicated by TLC using differentamounts of DABCO (Table 1) The efficiency of the reactionis mainly affected by the amount of the catalyst Traces ofthe product could be detected in the absence of this catalyst(entry 1) while good results were obtained in the presence ofDABCO The optimal amount of the catalyst was 10mmol(entry 6) the higher amount of the catalyst did not increasethe yield noticeably (entry 7)

The synthesized products 1(andashf) in Scheme 2were furthertreated with malononitrile to obtain corresponding alkyli-denes 2(andashf) by the Knoevenagel reaction The reactioninvolves the attack of malononitrile on two carbonyl groups(C=O) of xanthene derivatives to form alkylidene malonon-itrile within 60min using DABCO as an organic catalyst(Scheme 3)

In order to extend the range of substrates we employeda wide range of aldehydes in the presence of 10mmolDABCO under similar conditions It was found that thismethod is effective with a variety of substituted heteroary-laldehydes independent of the nature of the substituent onthe heteroaromatic ring and obtained satisfactory results(Table 2)

The formation of the products 1(andashf) was assumed toproceed via formation of a Knoevenagel product which onaddition of 2nd molecule to give the Michael adduct inter-mediate was followed by cyclization reaction (Scheme 4) An1205721205721015840-bis(arylidene)cycloalkanoneAwas first condensed withdimedone to afford the B on addition of 2nd molecule ofdimedone this step can be regarded as a Michael additionreaction The intermediate B was cyclized by nucleophilic

attack of the OH group on the C=C moiety and gave theexpected products 1(andashf)

3 Conclusion

In summary we have reported an efficient simple con-venient and straightforward practical one-pot procedurefor the synthesis of 1(andashf) in aqueous media Reactionof malononitrile on the synthesized products 1(andashf) gavecorresponding alkylidene derivatives 2(andashf) in good yieldsAll starting materials are readily available from commercialsources Moreover there is no need for dry solvents orprotecting gas atmospheres UsingDABCOas a catalyst offersadvantages including simplicity of operation easy workuptime minimizing and high yields of productsThe procedureis very simple and can be used as an alternative to the existingprocedures

4 Experimental

41 General The chemicals used in the synthesis of theoctahydroxanthene-18-dioneswere obtained from theMerckandAldrichChemical CoAll chemicals and solvents used forthe synthesis were of analytical reagent grade Reactions weremonitored by thin layer chromatography on 02mm silicagel F-252 (Merck) plates Melting points were determined byopen capillary method and were uncorrected1H (400MHz)and 13C (200MHz) spectra were recorded on Bruker 3000NMR spectrometer in CDCl

3DMSO-119889

6(with TMS for 1H

and CDCl3as internal references) unless otherwise specified

stated

42 General Procedure for the Synthesis of Heteroaryl Substi-tuted Xanthenes 1(andashf) A mixture of 5-membered hetero-arylaldehyde (1mmol) 55-dimethylcyclohexane-13-dione(2mmol) and DABCO (10mmol) in H

2O (20mL) was

refluxed for 30min The progress of the reaction was mon-itored by TLC After completion of the reaction the mixturewas cooled to room temperature and the solid was filteredoff and washed with H

2OThe crude product was purified by

recrystallization from 95 ethanol

43 General Procedure for the Synthesis of Alkylidenes 2(andashf) A mixture of heteroaryl substituted xanthenes (1mmol)malononitrile (2mmol) and DABCO (10mmol) in H

2O

(20mL) was stirred for 60min The progress of the reaction

ISRN Organic Chemistry 3

Table 2 Synthesis of heteroaryl substituted xanthenes and its alkylidene derivativesab

Entry X R1 R2 Time (min) Product Yield ()c MP (∘C)1 O H H 30 1a 94 168-1692 O H CH3 30 1b 92 158ndash1603 S H H 30 1c 95 142ndash1444 S CH3 H 30 1d 96 156-1575 S H CH3 30 1e 94 145ndash1476 NH H H 30 1f 87 88ndash907 O H H 60 2a 78 212-2138 O H CH3 60 2b 76 183ndash1859 S H H 60 2c 81 197-19810 S CH3 H 60 2d 77 170ndash17211 S H CH3 60 2e 83 177ndash17912 NH H H 60 2f 87 112ndash114aReaction conditions heteroarylaldehyde (1mmol) dimedone (2mmol) and DABCO (10mmol) in water (20mL) under reflux temperature bReactionconditions 1andashf (1mmol) malononitrile (2mmol) and DABCO (10mmol) in water (20mL) under reflux temperature cIsolated yields

XCHO

OO

O

O O

X

X

R2

R2

R1

R1DABCO H2O

Reflux 30min

=O S NHR1 and R2 = HCH3

2+

1(andashf)

Scheme 2

was monitored by TLC After completion of the reactionthe mixture was cooled to room temperature and the solidwas filtered off and washed with H

2O The crude product

was purified by column chromatographic technique usinghexane ethyl acetate

44 Spectral Data of Compounds

9-(Furan-2-yl)-3366-tetramethyl-345679-hexahydro-1H-xanthene-18(2H)-dione (1a) 1H NMR (400MHz CDCl

3) 120575

1014 (s 6H 2 times CH3) 1084 (s 6H 2 times CH

3) 2235 (s 4H

2 times CH2) 2425 (s 4H CH

2) 4941 (s 1H CH) 6159ndash6181

(m 2H Ar-H) 7133ndash7139 (d 1H Ar-H) IR 120584 3078 cmminus1(Ar-H) 2865 cmminus1 (Aliph CndashH) 1730 cmminus1 and 1673 cmminus1(C=O) 1602 cmminus1 (C=C) 1180 cmminus1 (CndashOndashC) Anal calcdfor C21H24O4 C 7409 H 711 found C 7403 H 707

3366-Tetramethyl-9-(5-methylfuran-2-yl)-345679-hexa-hydro-1H-xanthene-18(2H)-dione (1b) 1H NMR (400MHzCDCl

3) 120575 1039 (s 6H 2 timesCH

3) 1109 (s 6H 2 timesCH

3) 2109

(s 4H 2 timesCH2) 2551 (s 4H CH

2) 4832 (s 1H CH) 6108ndash

6226 (m 2H Ar-H) 3228 (s 3H Ar-CH3) IR 120584 3109 cmminus1

(Ar-H) 2905 cmminus1 (Alih CndashH) 1722 cmminus1 and 1688 cmminus1(C=O) 1630 cmminus1 (C=C) 1172 cmminus1 (CndashOndashC) Anal calcdfor C22H26O4 C 7455 H 739 found C 7528 H 688

3366-Tetramethyl-9-(thiophen-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-dione (1c) 1HNMR (400MHz CDCl

3)

120575 1208 (s 12H 4 timesCH3) 2109 (s 4H 2 timesCH

2) 2401 (s 4H

2 timesCH2) 4622 (s 1H CH) 6554 (d 1H Ar-H) 6828 (d 1H

Ar-H) 7298 (dd 1H Ar-H) IR 120584 3135 (Ar-H) 2920 cmminus1(Aliph CndashH) 1716 cmminus1 (C=O) 1648 cmminus1 and 1620 cmminus1(C=C) 1108 cmminus1 (CndashOndashC) Anal calcd for C

21H24O3S C

7075 H 679 S 899 found C 7133 H 628 S 849

3366-Tetramethyl-9-(3-methylthiophen-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-dione (1d) 1H NMR (400MHz CDCl

3) 120575 1100 (s 12H 4 times CH

3) 3035 (s 3H Ar-

CH3) 2281 (s 4H 2 times CH

2) 2544 (s 4H 2 times CH

2) 4875

(s 1H CH) 6478 (d 1H Ar-H) 6824 (d 1H Ar-H) IR120584 3042 cmminus1 (Ar-H) 2963 cmminus1 (CndashH) 1730 cmminus1 (C=O)1607 cmminus1 and 1588 cmminus1 (C=C) 1150 cmminus1 (CndashOndashC) Analcalcd for C

22H26O3S C 7132 H 707 S 865 found C 7128 H

709 S 869

3366-Tetramethyl-9-(5-methylthiophen-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-dione (1e) 1H NMR (400MHz CDCl

3) 120575 1288 (s 12H 4 times CH

3) 2988 (s 3H

Ar-CH3) 2448 (s 4H 2 times CH

2) 2722 (s 4H 2 times CH

2)

4658 (s 1H CH) 6234 (d 1H Ar-H) 6775 (d 1H Ar-H)IR 120584 3090 cmminus1 (Ar-H) 2882 cmminus1 (Aliph CndashH) 1716 cmminus1

4 ISRN Organic Chemistry

O

O O

X

CN

CN

2

O

X

CNNC CNNC

R2R2

R1R1

DABCO H2OReflux 30ndash60min+

2(andashf)1(andashf)

Scheme 3

OO OHOArH

O

DABCOOO

Ar O

HOKnoevenagel

O

O

Ar O O

O

Ar O

O

DABCOMichael addition

Cyclization

1st molecule

minusH2O

minusH2O

2nd molecule

B

A

1(andashf)

Scheme 4

(C=O) 1632 cmminus1 and 1610 cmminus1 (C=C) 1148 cmminus1 (CndashOndashC)Anal calcd for C

22H26O3S C 7132 H 707 S 865 found C

7154 H 768 S 914

3366-Tetramethyl-9-(1H-pyrrol-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-dione (1f) 1HNMR (400MHz CDCl

3)

120575 1018ndash1146 (m 12H 4 times CH3) 2154 (br s 8H 4 times CH

2

5601 (s 1H CH) 6957ndash6970 (s 1H Ar-H) 6698ndash6710 (d1H Ar-H) 6162 (dd 1H Ar-H) 9570 (br s 1H NH) IR120584 3397 cmminus1 3328 cmminus1 (NndashH) 3065 cmminus1 (Ar-H) 2978v(Aliph CndashH) 1680 cmminus1 (C=O) 1604 cmminus1 and 1469 cmminus1(C=C) 1145 cmminus1 (COC) Anal calcd for C

21H25NO3 C

7431 H 742 N 413 found C 7426 H 746 N 415

221015840-(3366-Tetramethyl-9-(furan-2-yl)-345679-hexa-hydro-1H-xanthene-18(2H)-diylidene)dimalononitrile (2a)1H NMR (400MHz CDCl

3) 120575 1016 (s 6H 2 times CH

3) 1128

(s 6H 2 times CH3) 2246 (s 4H 2 times CH

2) 2665 (s 4H CH

2)

4941 (s 1H CH) 6154ndash6188 (m 2H Ar-H) 7138ndash7144 (d1H Ar-H) IR 120584 3078 cmminus1 (Ar-H) 2865 cmminus1 (aliph CndashH)2224 cmminus1 (CN) 1716 cmminus1 and 1684 cmminus1 (C=O) 1620 cmminus1(C=C) 1154 cmminus1 (CndashOndashC) Anal calcd for C

27H24N4O2 C

7429 H 554 N 1284 found C 7382 H 569 N 1209

221015840-(3366-Tetramethyl-9-(5-methylfuran-2-yl)-345679-hexahydro-1H-xanthene-18(2H-diylidene)dimalononitrile(2b) 1H NMR (400MHz CDCl

3) 120575 0986 (s 6H 2 times CH

3)

1235 (s 6H 2 times CH3) 2244 (s 4H 2 times CH

2) 2658 (s

4H CH2) 4988 (s 1H CH) 6159ndash6181 (m 2H Ar-H)

3286 (s 3H Ar-CH3) IR 120584 3058 cmminus1 (Ar-H) 2944 cmminus1

(Aliph CndashH) 2224 cmminus1 (CN) 1714 cmminus1 and 1682 cmminus1(C=O) 1622 cmminus1 (C=C) 1144 cmminus1 (CndashOndashC) Anal calcdfor C28H26N4O2 C 7465 H 582 N 1244 found C 7511 H

608 N 1188

221015840-(3366-Tetramethyl-9-(thiophen-2-yl)-345679-hexa-hydro-1H-xanthene-18(2H)-diylidene)dimalononitrile (2c)1H NMR (400MHz CDCl

3) 120575 1029 (s 6H 2 times CH

3) 1208

(s 6H 2 times CH3) 2248 (s 4H 2 times CH

2) 2659 (s 4H CH

2)

4745 (s 1H CH) 6686ndash6789 (m 2H Ar-H) 7252ndash7263 (d1H Ar-H) IR 120584 3078 cmminus1 (Ar-H) 2988 cmminus1 (Aliph CndashH)2224 cmminus1 (CN) 1710 cmminus1 and 1688 cmminus1 (C=O) 1626 cmminus1(C=C) 1164 cmminus1 (CndashOndashC) Anal calcd for C

27H24N4OS C

7165 H 535 N 1284 S 709 found C 7118 H 574 N 1212 S783

221015840-(3366-Tetramethyl-9-(3-methylthiophen-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-diylidene)dimalononitrile(2d) 1H NMR (400MHz CDCl

3) 120575 1044 (s 6H 2 times CH

3)

1301 (s 6H 2 times CH3) 2144 (s 4H 2 times CH

2) 2656 (s

4H CH2) 4886 (s 1H CH) 6136ndash6172 (m 2H Ar-H)

3114 (s 3H Ar-CH3) IR 120584 3098 cmminus1 (Ar-H) 2898 cmminus1

(Aliph CndashH) 2224 cmminus1 (CN) 1710 cmminus1 and 1682 cmminus1(C=O) 1663 cmminus1 (C=C) 1156 cmminus1 (CndashOndashC) Anal calcd

ISRN Organic Chemistry 5

for C28H26N4OS C 7207 H 562 N 1201 S 687 found C

7112 H 528 N 1284 S 715

221015840-(3366-Tetramethyl-9-(5-methylthiophen-2-yl)- 345679-hexahydro-1H-xanthene-18(2H-diylidene)dimalononitrile(2e) 1H NMR (400MHz CDCl

3) 120575 1022 (s 6H 2 times CH

3)

1308 (s 6H 2 times CH3) 2224 (s 4H 2 times CH

2) 2538 (s

4H CH2) 4908 (s 1H CH) 6108ndash6191 (m 2H Ar-H)

3257 (s 3H Ar-CH3) IR 120584 3086 cmminus1 (Ar-H) 2910 cmminus1

(Aliph CndashH) 2224 cmminus1 (CN) 1728 cmminus1 and 1692 cmminus1(C=O) 1605 cmminus1 (C=C) 1162 cmminus1 (CndashOndashC) Anal calcdfor C28H26N4OS C 7207 H 562 N 1201 S 687 found C

7143 H 512 N 1277 S 725

221015840-(3366-Tetramethyl-9-(pyrrol-2-yl)-345679-hexahyd-ro-1H-xanthene-18(2H)-diylidene)dimalononitrile (2f) 1HNMR (400MHz CDCl

3) 120575 1022 (s 6H 2 times CH

3) 1063(s

6H 2 times CH3) 2268 (s 4H 2 times CH

2) 2569 (s 4H CH

2)

4858 (s 1H CH) 6168ndash6198 (m 2H Ar-H) 7124ndash7138 (d1H Ar-H) 8986 (br s 1H NH) IR 120584 3064 cmminus1 (Ar-H)2936 cmminus1 (Aliph CndashH) 2224 cmminus1 (CN) 1710 cmminus1 and1678 cmminus1 (C=O) 1619 cmminus1 (C=C) 1166 cmminus1 (COC) Analcalcd for C

21H24O4 C 7446 H 579 found C 7412 H 608

Acknowledgments

Theauthors are thankful to theDirector of SAIF IITMumbaifor spectral analysis and Dr Asutosh K Pandey Departmentof Engineering Chemistry Oriental University Indore (MP)for valuable suggestions

References

[1] R V A Orru and M De Greef ldquoRecent advances in solution-phase multicomponent methodology for the synthesis of hete-rocyclic compoundsrdquo Synthesis no 10 pp 1471ndash1499 2003

[2] A Domling ldquoRecent developments in isocyanide-based multi-component reactions in applied chemistryrdquo Chemical Reviewsvol 106 no 1 pp 17ndash89 2006

[3] A Domling and I Ugi ldquoMulticomponent reactions with iso-cyanidesrdquoAngewandte Chemie International Edition vol 39 no18 pp 3168ndash3210 2000

[4] J Peng W Hao X Wang S Tu N Ma and G ZhangldquoMicrowave-assisted synthesis of pyrazolo[43-f ]quinolin-7-one derivatives viamulti-component reactionsrdquoChinese Journalof Chemistry vol 27 no 9 pp 1707ndash1710 2009

[5] L F Tietze H Evers and E Topken ldquoA novel concept in com-binatorial chemistry in solution with the advantages of solid-phase synthesis formation of N-betaines by multicomponentdomino reactionsrdquo Angewandte Chemie International Editionvol 40 no 5 pp 903ndash905 2001

[6] T Masquelin H Bui B Brickley G Stephenson J Schw-erkoske and C Hulme ldquoSequential UgiStrecker reactionsvia microwave assisted organic synthesis novel 3-center-4-component and 3-center-5-component multi-component reac-tionsrdquo Tetrahedron Letters vol 47 no 17 pp 2989ndash2991 2006

[7] A Djande M Kiendrebeogo M Compaore et al ldquoAntioxidantpotential of 4-acyl isochroman-1 3-dionesrdquo Research Journal ofChemical Sciences vol 1 no 5 pp 88ndash90 2011

[8] S M Menchen S C Benson J Y L Lam et al Patent US6583168 2003

[9] C G Knight and T Stephens ldquoXanthene-dye-labelled phos-phatidylethanolamines as probes of interfacial pH Studies inphospholipid vesiclesrdquo Biochemical Journal vol 258 no 3 pp683ndash689 1989

[10] A K Bhattacharya and K C Rana ldquoMicrowave-assisted syn-thesis of 14-aryl-14H-dibenzo[aj]xanthenes catalysed by pTSAin solution and solvent-free conditionsrdquo Mendeleev Communi-cations vol 17 no 4 pp 247ndash248 2007

[11] G Mulongo J Mbabazi B Odongkara H Twinomuhwezi andG B Mpango ldquoNew biologically active compounds from 1 3-diketonesrdquo Research Journal of Chemical Sciences vol 1 no 3pp 102ndash108 2011

[12] Z Karimi-Jaberi and M M Hashemi ldquoOne step synthesisof 14-alkyl- or aryl-14H-dibenzo[aj]xanthenes using sodiumhydrogen sulfate as catalystrdquo Monatshefte fur Chemie vol 139no 6 pp 605ndash608 2008

[13] M Seyyedhamzeh P Mirzaei and A Bazgir ldquoSolvent-freesynthesis of aryl-14H-dibenzo[aj]xanthenes and 18-dioxo-octahydro-xanthenes using silica sulfuric acid as catalystrdquoDyesand Pigments vol 76 no 3 pp 836ndash839 2008

[14] J QWang and R G Harvey ldquoSynthesis of polycyclic xanthenesand furans via palladium-catalyzed cyclization of polycyclicaryltriflate estersrdquo Tetrahedron vol 58 no 29 pp 5927ndash59312002

[15] G Casiraghi G Casnati M Catellani and M A A CorinaldquoConvenient one-step synthesis of xanthene derivativesrdquo Syn-thesis no 8 pp 564ndash564 1974

[16] S Gupta P Gupta A Sachar and R L Sharma ldquoSyntheticstudies of some varied structural systems of biologically potentpolynitrogen heteropolycyclicsrdquo Indian Journal of Chemistry Bvol 49 no 9 pp 1243ndash1256 2010

[17] M H Majid A Hamideh B Khadijeh S Mina A O Hosseinand F B Fatemeh ldquoSolvent-free synthesis of xanthenes deriva-tives by preyssler type heteropolyacidrdquo Bulletin of ChemicalSociety of Ethiopia vol 25 no 3 pp 399ndash406 2011

[18] K Muharrem ldquoAldol condensation and michael addition of4 4-dimethylcyclohexane-1 3-dione and aromatic aldehydesUnconventional substituent effectsrdquo Chinese Journal of Chem-istry vol 29 no 11 pp 2355ndash2360 2011

[19] A Ilangovan S Malayappasamy S Muralidharan and SMaruthamuthu ldquoA highly efficient green synthesis of 1 8-dioxooctahydroxanthenesrdquo Chemistry Central Journal vol 5pp 81ndash86 2011

[20] B Baghernejad ldquo4-Diazabicyclo [222] octane (DABCO) asa useful catalyst in organic synthesisrdquo European Journal ofChemistry vol 1 no 1 pp 54ndash60 2010

[21] H Yang R Tian and Y Li ldquoOrganic reactions catalyzed by 14-diazabicyclo [222] octane (DABCO)rdquo Frontiers of Chemistryin China vol 3 no 3 pp 279ndash287 2008

[22] X Da-Zhen Y Liu S Shi and Y Wang ldquoA simple efficientand green procedure for Knoevenagel condensation catalyzedby [C

4dabco][BF

4] ionic liquid in waterrdquo Green Chemistry vol

12 no 3 pp 514ndash517 2010[23] M Bigdeli ldquoClean synthesis of 18-dioxooctahydroxanthenes

promoted by DABCO-bromine in aqueous mediardquo ChineseChemical Letters vol 21 no 10 pp 1180ndash1182 2010

[24] B Saeed R Sorour B Morteza and H G Jurgen ldquoDABCO-catalyzed efficient synthesis of naphthopyran derivatives viaone-pot three-component condensation reaction at room tem-peraturerdquo Synthetic Communications vol 38 no 7 pp 1078ndash1089 2008

6 ISRN Organic Chemistry

[25] K Y Lee J M Kim and J N Kim ldquoSynthesis of 2344a-tet-tetrahydroxanthenrahydroxanthen-1-ones and 33a-dihydro-2H-cyclopenta[b]chromen-1-ones from the reaction of salicy-laldehydes and 2-cyclohexen-1-one and 2-cyclopenten-1-onerdquoBulletin of the Korean Chemical Society vol 24 no 1 pp 17ndash182003

[26] S Jain G N Babu S R Jetti S Harshada andD SuryaprakashldquoSynthesis antitubercular and antifungal activities of heteroaryl-substituted oxirance derived from Baylis-Hillman adductsrdquoMedicinal Chemistry Research vol 21 no 10 pp 2744ndash27482012

[27] S Jain P Paliwal and G N Babu ldquoDABCO promoted one-pot synthesis of dihydro pyrano(c) chromene and pyrano[2 3-d]pyrimidine derivatives and their biological activitiesrdquo Journalof Saudi Chemical Society 2011

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CatalystsJournal of

2 ISRN Organic Chemistry

O

O

COOHAzido analogue

O

O

O

Rhodamine 123

NH2H2

N3

N

H3C

+

Scheme 1

Table 1 Influence of the amounts of DABCO on the synthesis of 1dat reflux temperaturea

Entry Catalyst Amount of catalyst Time (min) Yieldb ()(mmol)

1 None mdash 80 Trace2 DABCO 1 70 673 DABCO 2 60 744 DABCO 3 50 825 DABCO 5 40 896 DABCO 10 30 967 DABCO 15 30 96aReaction conditions 3-methyl thienaldehyde (1mmol) dimedone (2mmol)in water (20mL) under reflux temperature bIsolated yields

an appropriate time as indicated by TLC using differentamounts of DABCO (Table 1) The efficiency of the reactionis mainly affected by the amount of the catalyst Traces ofthe product could be detected in the absence of this catalyst(entry 1) while good results were obtained in the presence ofDABCO The optimal amount of the catalyst was 10mmol(entry 6) the higher amount of the catalyst did not increasethe yield noticeably (entry 7)

The synthesized products 1(andashf) in Scheme 2were furthertreated with malononitrile to obtain corresponding alkyli-denes 2(andashf) by the Knoevenagel reaction The reactioninvolves the attack of malononitrile on two carbonyl groups(C=O) of xanthene derivatives to form alkylidene malonon-itrile within 60min using DABCO as an organic catalyst(Scheme 3)

In order to extend the range of substrates we employeda wide range of aldehydes in the presence of 10mmolDABCO under similar conditions It was found that thismethod is effective with a variety of substituted heteroary-laldehydes independent of the nature of the substituent onthe heteroaromatic ring and obtained satisfactory results(Table 2)

The formation of the products 1(andashf) was assumed toproceed via formation of a Knoevenagel product which onaddition of 2nd molecule to give the Michael adduct inter-mediate was followed by cyclization reaction (Scheme 4) An1205721205721015840-bis(arylidene)cycloalkanoneAwas first condensed withdimedone to afford the B on addition of 2nd molecule ofdimedone this step can be regarded as a Michael additionreaction The intermediate B was cyclized by nucleophilic

attack of the OH group on the C=C moiety and gave theexpected products 1(andashf)

3 Conclusion

In summary we have reported an efficient simple con-venient and straightforward practical one-pot procedurefor the synthesis of 1(andashf) in aqueous media Reactionof malononitrile on the synthesized products 1(andashf) gavecorresponding alkylidene derivatives 2(andashf) in good yieldsAll starting materials are readily available from commercialsources Moreover there is no need for dry solvents orprotecting gas atmospheres UsingDABCOas a catalyst offersadvantages including simplicity of operation easy workuptime minimizing and high yields of productsThe procedureis very simple and can be used as an alternative to the existingprocedures

4 Experimental

41 General The chemicals used in the synthesis of theoctahydroxanthene-18-dioneswere obtained from theMerckandAldrichChemical CoAll chemicals and solvents used forthe synthesis were of analytical reagent grade Reactions weremonitored by thin layer chromatography on 02mm silicagel F-252 (Merck) plates Melting points were determined byopen capillary method and were uncorrected1H (400MHz)and 13C (200MHz) spectra were recorded on Bruker 3000NMR spectrometer in CDCl

3DMSO-119889

6(with TMS for 1H

and CDCl3as internal references) unless otherwise specified

stated

42 General Procedure for the Synthesis of Heteroaryl Substi-tuted Xanthenes 1(andashf) A mixture of 5-membered hetero-arylaldehyde (1mmol) 55-dimethylcyclohexane-13-dione(2mmol) and DABCO (10mmol) in H

2O (20mL) was

refluxed for 30min The progress of the reaction was mon-itored by TLC After completion of the reaction the mixturewas cooled to room temperature and the solid was filteredoff and washed with H

2OThe crude product was purified by

recrystallization from 95 ethanol

43 General Procedure for the Synthesis of Alkylidenes 2(andashf) A mixture of heteroaryl substituted xanthenes (1mmol)malononitrile (2mmol) and DABCO (10mmol) in H

2O

(20mL) was stirred for 60min The progress of the reaction

ISRN Organic Chemistry 3

Table 2 Synthesis of heteroaryl substituted xanthenes and its alkylidene derivativesab

Entry X R1 R2 Time (min) Product Yield ()c MP (∘C)1 O H H 30 1a 94 168-1692 O H CH3 30 1b 92 158ndash1603 S H H 30 1c 95 142ndash1444 S CH3 H 30 1d 96 156-1575 S H CH3 30 1e 94 145ndash1476 NH H H 30 1f 87 88ndash907 O H H 60 2a 78 212-2138 O H CH3 60 2b 76 183ndash1859 S H H 60 2c 81 197-19810 S CH3 H 60 2d 77 170ndash17211 S H CH3 60 2e 83 177ndash17912 NH H H 60 2f 87 112ndash114aReaction conditions heteroarylaldehyde (1mmol) dimedone (2mmol) and DABCO (10mmol) in water (20mL) under reflux temperature bReactionconditions 1andashf (1mmol) malononitrile (2mmol) and DABCO (10mmol) in water (20mL) under reflux temperature cIsolated yields

XCHO

OO

O

O O

X

X

R2

R2

R1

R1DABCO H2O

Reflux 30min

=O S NHR1 and R2 = HCH3

2+

1(andashf)

Scheme 2

was monitored by TLC After completion of the reactionthe mixture was cooled to room temperature and the solidwas filtered off and washed with H

2O The crude product

was purified by column chromatographic technique usinghexane ethyl acetate

44 Spectral Data of Compounds

9-(Furan-2-yl)-3366-tetramethyl-345679-hexahydro-1H-xanthene-18(2H)-dione (1a) 1H NMR (400MHz CDCl

3) 120575

1014 (s 6H 2 times CH3) 1084 (s 6H 2 times CH

3) 2235 (s 4H

2 times CH2) 2425 (s 4H CH

2) 4941 (s 1H CH) 6159ndash6181

(m 2H Ar-H) 7133ndash7139 (d 1H Ar-H) IR 120584 3078 cmminus1(Ar-H) 2865 cmminus1 (Aliph CndashH) 1730 cmminus1 and 1673 cmminus1(C=O) 1602 cmminus1 (C=C) 1180 cmminus1 (CndashOndashC) Anal calcdfor C21H24O4 C 7409 H 711 found C 7403 H 707

3366-Tetramethyl-9-(5-methylfuran-2-yl)-345679-hexa-hydro-1H-xanthene-18(2H)-dione (1b) 1H NMR (400MHzCDCl

3) 120575 1039 (s 6H 2 timesCH

3) 1109 (s 6H 2 timesCH

3) 2109

(s 4H 2 timesCH2) 2551 (s 4H CH

2) 4832 (s 1H CH) 6108ndash

6226 (m 2H Ar-H) 3228 (s 3H Ar-CH3) IR 120584 3109 cmminus1

(Ar-H) 2905 cmminus1 (Alih CndashH) 1722 cmminus1 and 1688 cmminus1(C=O) 1630 cmminus1 (C=C) 1172 cmminus1 (CndashOndashC) Anal calcdfor C22H26O4 C 7455 H 739 found C 7528 H 688

3366-Tetramethyl-9-(thiophen-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-dione (1c) 1HNMR (400MHz CDCl

3)

120575 1208 (s 12H 4 timesCH3) 2109 (s 4H 2 timesCH

2) 2401 (s 4H

2 timesCH2) 4622 (s 1H CH) 6554 (d 1H Ar-H) 6828 (d 1H

Ar-H) 7298 (dd 1H Ar-H) IR 120584 3135 (Ar-H) 2920 cmminus1(Aliph CndashH) 1716 cmminus1 (C=O) 1648 cmminus1 and 1620 cmminus1(C=C) 1108 cmminus1 (CndashOndashC) Anal calcd for C

21H24O3S C

7075 H 679 S 899 found C 7133 H 628 S 849

3366-Tetramethyl-9-(3-methylthiophen-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-dione (1d) 1H NMR (400MHz CDCl

3) 120575 1100 (s 12H 4 times CH

3) 3035 (s 3H Ar-

CH3) 2281 (s 4H 2 times CH

2) 2544 (s 4H 2 times CH

2) 4875

(s 1H CH) 6478 (d 1H Ar-H) 6824 (d 1H Ar-H) IR120584 3042 cmminus1 (Ar-H) 2963 cmminus1 (CndashH) 1730 cmminus1 (C=O)1607 cmminus1 and 1588 cmminus1 (C=C) 1150 cmminus1 (CndashOndashC) Analcalcd for C

22H26O3S C 7132 H 707 S 865 found C 7128 H

709 S 869

3366-Tetramethyl-9-(5-methylthiophen-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-dione (1e) 1H NMR (400MHz CDCl

3) 120575 1288 (s 12H 4 times CH

3) 2988 (s 3H

Ar-CH3) 2448 (s 4H 2 times CH

2) 2722 (s 4H 2 times CH

2)

4658 (s 1H CH) 6234 (d 1H Ar-H) 6775 (d 1H Ar-H)IR 120584 3090 cmminus1 (Ar-H) 2882 cmminus1 (Aliph CndashH) 1716 cmminus1

4 ISRN Organic Chemistry

O

O O

X

CN

CN

2

O

X

CNNC CNNC

R2R2

R1R1

DABCO H2OReflux 30ndash60min+

2(andashf)1(andashf)

Scheme 3

OO OHOArH

O

DABCOOO

Ar O

HOKnoevenagel

O

O

Ar O O

O

Ar O

O

DABCOMichael addition

Cyclization

1st molecule

minusH2O

minusH2O

2nd molecule

B

A

1(andashf)

Scheme 4

(C=O) 1632 cmminus1 and 1610 cmminus1 (C=C) 1148 cmminus1 (CndashOndashC)Anal calcd for C

22H26O3S C 7132 H 707 S 865 found C

7154 H 768 S 914

3366-Tetramethyl-9-(1H-pyrrol-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-dione (1f) 1HNMR (400MHz CDCl

3)

120575 1018ndash1146 (m 12H 4 times CH3) 2154 (br s 8H 4 times CH

2

5601 (s 1H CH) 6957ndash6970 (s 1H Ar-H) 6698ndash6710 (d1H Ar-H) 6162 (dd 1H Ar-H) 9570 (br s 1H NH) IR120584 3397 cmminus1 3328 cmminus1 (NndashH) 3065 cmminus1 (Ar-H) 2978v(Aliph CndashH) 1680 cmminus1 (C=O) 1604 cmminus1 and 1469 cmminus1(C=C) 1145 cmminus1 (COC) Anal calcd for C

21H25NO3 C

7431 H 742 N 413 found C 7426 H 746 N 415

221015840-(3366-Tetramethyl-9-(furan-2-yl)-345679-hexa-hydro-1H-xanthene-18(2H)-diylidene)dimalononitrile (2a)1H NMR (400MHz CDCl

3) 120575 1016 (s 6H 2 times CH

3) 1128

(s 6H 2 times CH3) 2246 (s 4H 2 times CH

2) 2665 (s 4H CH

2)

4941 (s 1H CH) 6154ndash6188 (m 2H Ar-H) 7138ndash7144 (d1H Ar-H) IR 120584 3078 cmminus1 (Ar-H) 2865 cmminus1 (aliph CndashH)2224 cmminus1 (CN) 1716 cmminus1 and 1684 cmminus1 (C=O) 1620 cmminus1(C=C) 1154 cmminus1 (CndashOndashC) Anal calcd for C

27H24N4O2 C

7429 H 554 N 1284 found C 7382 H 569 N 1209

221015840-(3366-Tetramethyl-9-(5-methylfuran-2-yl)-345679-hexahydro-1H-xanthene-18(2H-diylidene)dimalononitrile(2b) 1H NMR (400MHz CDCl

3) 120575 0986 (s 6H 2 times CH

3)

1235 (s 6H 2 times CH3) 2244 (s 4H 2 times CH

2) 2658 (s

4H CH2) 4988 (s 1H CH) 6159ndash6181 (m 2H Ar-H)

3286 (s 3H Ar-CH3) IR 120584 3058 cmminus1 (Ar-H) 2944 cmminus1

(Aliph CndashH) 2224 cmminus1 (CN) 1714 cmminus1 and 1682 cmminus1(C=O) 1622 cmminus1 (C=C) 1144 cmminus1 (CndashOndashC) Anal calcdfor C28H26N4O2 C 7465 H 582 N 1244 found C 7511 H

608 N 1188

221015840-(3366-Tetramethyl-9-(thiophen-2-yl)-345679-hexa-hydro-1H-xanthene-18(2H)-diylidene)dimalononitrile (2c)1H NMR (400MHz CDCl

3) 120575 1029 (s 6H 2 times CH

3) 1208

(s 6H 2 times CH3) 2248 (s 4H 2 times CH

2) 2659 (s 4H CH

2)

4745 (s 1H CH) 6686ndash6789 (m 2H Ar-H) 7252ndash7263 (d1H Ar-H) IR 120584 3078 cmminus1 (Ar-H) 2988 cmminus1 (Aliph CndashH)2224 cmminus1 (CN) 1710 cmminus1 and 1688 cmminus1 (C=O) 1626 cmminus1(C=C) 1164 cmminus1 (CndashOndashC) Anal calcd for C

27H24N4OS C

7165 H 535 N 1284 S 709 found C 7118 H 574 N 1212 S783

221015840-(3366-Tetramethyl-9-(3-methylthiophen-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-diylidene)dimalononitrile(2d) 1H NMR (400MHz CDCl

3) 120575 1044 (s 6H 2 times CH

3)

1301 (s 6H 2 times CH3) 2144 (s 4H 2 times CH

2) 2656 (s

4H CH2) 4886 (s 1H CH) 6136ndash6172 (m 2H Ar-H)

3114 (s 3H Ar-CH3) IR 120584 3098 cmminus1 (Ar-H) 2898 cmminus1

(Aliph CndashH) 2224 cmminus1 (CN) 1710 cmminus1 and 1682 cmminus1(C=O) 1663 cmminus1 (C=C) 1156 cmminus1 (CndashOndashC) Anal calcd

ISRN Organic Chemistry 5

for C28H26N4OS C 7207 H 562 N 1201 S 687 found C

7112 H 528 N 1284 S 715

221015840-(3366-Tetramethyl-9-(5-methylthiophen-2-yl)- 345679-hexahydro-1H-xanthene-18(2H-diylidene)dimalononitrile(2e) 1H NMR (400MHz CDCl

3) 120575 1022 (s 6H 2 times CH

3)

1308 (s 6H 2 times CH3) 2224 (s 4H 2 times CH

2) 2538 (s

4H CH2) 4908 (s 1H CH) 6108ndash6191 (m 2H Ar-H)

3257 (s 3H Ar-CH3) IR 120584 3086 cmminus1 (Ar-H) 2910 cmminus1

(Aliph CndashH) 2224 cmminus1 (CN) 1728 cmminus1 and 1692 cmminus1(C=O) 1605 cmminus1 (C=C) 1162 cmminus1 (CndashOndashC) Anal calcdfor C28H26N4OS C 7207 H 562 N 1201 S 687 found C

7143 H 512 N 1277 S 725

221015840-(3366-Tetramethyl-9-(pyrrol-2-yl)-345679-hexahyd-ro-1H-xanthene-18(2H)-diylidene)dimalononitrile (2f) 1HNMR (400MHz CDCl

3) 120575 1022 (s 6H 2 times CH

3) 1063(s

6H 2 times CH3) 2268 (s 4H 2 times CH

2) 2569 (s 4H CH

2)

4858 (s 1H CH) 6168ndash6198 (m 2H Ar-H) 7124ndash7138 (d1H Ar-H) 8986 (br s 1H NH) IR 120584 3064 cmminus1 (Ar-H)2936 cmminus1 (Aliph CndashH) 2224 cmminus1 (CN) 1710 cmminus1 and1678 cmminus1 (C=O) 1619 cmminus1 (C=C) 1166 cmminus1 (COC) Analcalcd for C

21H24O4 C 7446 H 579 found C 7412 H 608

Acknowledgments

Theauthors are thankful to theDirector of SAIF IITMumbaifor spectral analysis and Dr Asutosh K Pandey Departmentof Engineering Chemistry Oriental University Indore (MP)for valuable suggestions

References

[1] R V A Orru and M De Greef ldquoRecent advances in solution-phase multicomponent methodology for the synthesis of hete-rocyclic compoundsrdquo Synthesis no 10 pp 1471ndash1499 2003

[2] A Domling ldquoRecent developments in isocyanide-based multi-component reactions in applied chemistryrdquo Chemical Reviewsvol 106 no 1 pp 17ndash89 2006

[3] A Domling and I Ugi ldquoMulticomponent reactions with iso-cyanidesrdquoAngewandte Chemie International Edition vol 39 no18 pp 3168ndash3210 2000

[4] J Peng W Hao X Wang S Tu N Ma and G ZhangldquoMicrowave-assisted synthesis of pyrazolo[43-f ]quinolin-7-one derivatives viamulti-component reactionsrdquoChinese Journalof Chemistry vol 27 no 9 pp 1707ndash1710 2009

[5] L F Tietze H Evers and E Topken ldquoA novel concept in com-binatorial chemistry in solution with the advantages of solid-phase synthesis formation of N-betaines by multicomponentdomino reactionsrdquo Angewandte Chemie International Editionvol 40 no 5 pp 903ndash905 2001

[6] T Masquelin H Bui B Brickley G Stephenson J Schw-erkoske and C Hulme ldquoSequential UgiStrecker reactionsvia microwave assisted organic synthesis novel 3-center-4-component and 3-center-5-component multi-component reac-tionsrdquo Tetrahedron Letters vol 47 no 17 pp 2989ndash2991 2006

[7] A Djande M Kiendrebeogo M Compaore et al ldquoAntioxidantpotential of 4-acyl isochroman-1 3-dionesrdquo Research Journal ofChemical Sciences vol 1 no 5 pp 88ndash90 2011

[8] S M Menchen S C Benson J Y L Lam et al Patent US6583168 2003

[9] C G Knight and T Stephens ldquoXanthene-dye-labelled phos-phatidylethanolamines as probes of interfacial pH Studies inphospholipid vesiclesrdquo Biochemical Journal vol 258 no 3 pp683ndash689 1989

[10] A K Bhattacharya and K C Rana ldquoMicrowave-assisted syn-thesis of 14-aryl-14H-dibenzo[aj]xanthenes catalysed by pTSAin solution and solvent-free conditionsrdquo Mendeleev Communi-cations vol 17 no 4 pp 247ndash248 2007

[11] G Mulongo J Mbabazi B Odongkara H Twinomuhwezi andG B Mpango ldquoNew biologically active compounds from 1 3-diketonesrdquo Research Journal of Chemical Sciences vol 1 no 3pp 102ndash108 2011

[12] Z Karimi-Jaberi and M M Hashemi ldquoOne step synthesisof 14-alkyl- or aryl-14H-dibenzo[aj]xanthenes using sodiumhydrogen sulfate as catalystrdquo Monatshefte fur Chemie vol 139no 6 pp 605ndash608 2008

[13] M Seyyedhamzeh P Mirzaei and A Bazgir ldquoSolvent-freesynthesis of aryl-14H-dibenzo[aj]xanthenes and 18-dioxo-octahydro-xanthenes using silica sulfuric acid as catalystrdquoDyesand Pigments vol 76 no 3 pp 836ndash839 2008

[14] J QWang and R G Harvey ldquoSynthesis of polycyclic xanthenesand furans via palladium-catalyzed cyclization of polycyclicaryltriflate estersrdquo Tetrahedron vol 58 no 29 pp 5927ndash59312002

[15] G Casiraghi G Casnati M Catellani and M A A CorinaldquoConvenient one-step synthesis of xanthene derivativesrdquo Syn-thesis no 8 pp 564ndash564 1974

[16] S Gupta P Gupta A Sachar and R L Sharma ldquoSyntheticstudies of some varied structural systems of biologically potentpolynitrogen heteropolycyclicsrdquo Indian Journal of Chemistry Bvol 49 no 9 pp 1243ndash1256 2010

[17] M H Majid A Hamideh B Khadijeh S Mina A O Hosseinand F B Fatemeh ldquoSolvent-free synthesis of xanthenes deriva-tives by preyssler type heteropolyacidrdquo Bulletin of ChemicalSociety of Ethiopia vol 25 no 3 pp 399ndash406 2011

[18] K Muharrem ldquoAldol condensation and michael addition of4 4-dimethylcyclohexane-1 3-dione and aromatic aldehydesUnconventional substituent effectsrdquo Chinese Journal of Chem-istry vol 29 no 11 pp 2355ndash2360 2011

[19] A Ilangovan S Malayappasamy S Muralidharan and SMaruthamuthu ldquoA highly efficient green synthesis of 1 8-dioxooctahydroxanthenesrdquo Chemistry Central Journal vol 5pp 81ndash86 2011

[20] B Baghernejad ldquo4-Diazabicyclo [222] octane (DABCO) asa useful catalyst in organic synthesisrdquo European Journal ofChemistry vol 1 no 1 pp 54ndash60 2010

[21] H Yang R Tian and Y Li ldquoOrganic reactions catalyzed by 14-diazabicyclo [222] octane (DABCO)rdquo Frontiers of Chemistryin China vol 3 no 3 pp 279ndash287 2008

[22] X Da-Zhen Y Liu S Shi and Y Wang ldquoA simple efficientand green procedure for Knoevenagel condensation catalyzedby [C

4dabco][BF

4] ionic liquid in waterrdquo Green Chemistry vol

12 no 3 pp 514ndash517 2010[23] M Bigdeli ldquoClean synthesis of 18-dioxooctahydroxanthenes

promoted by DABCO-bromine in aqueous mediardquo ChineseChemical Letters vol 21 no 10 pp 1180ndash1182 2010

[24] B Saeed R Sorour B Morteza and H G Jurgen ldquoDABCO-catalyzed efficient synthesis of naphthopyran derivatives viaone-pot three-component condensation reaction at room tem-peraturerdquo Synthetic Communications vol 38 no 7 pp 1078ndash1089 2008

6 ISRN Organic Chemistry

[25] K Y Lee J M Kim and J N Kim ldquoSynthesis of 2344a-tet-tetrahydroxanthenrahydroxanthen-1-ones and 33a-dihydro-2H-cyclopenta[b]chromen-1-ones from the reaction of salicy-laldehydes and 2-cyclohexen-1-one and 2-cyclopenten-1-onerdquoBulletin of the Korean Chemical Society vol 24 no 1 pp 17ndash182003

[26] S Jain G N Babu S R Jetti S Harshada andD SuryaprakashldquoSynthesis antitubercular and antifungal activities of heteroaryl-substituted oxirance derived from Baylis-Hillman adductsrdquoMedicinal Chemistry Research vol 21 no 10 pp 2744ndash27482012

[27] S Jain P Paliwal and G N Babu ldquoDABCO promoted one-pot synthesis of dihydro pyrano(c) chromene and pyrano[2 3-d]pyrimidine derivatives and their biological activitiesrdquo Journalof Saudi Chemical Society 2011

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

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Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

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Medicinal ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Chromatography Research International

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Applied ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Theoretical ChemistryJournal of

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Journal of

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Journal of

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Quantum Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Organic Chemistry International

ElectrochemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

CatalystsJournal of

ISRN Organic Chemistry 3

Table 2 Synthesis of heteroaryl substituted xanthenes and its alkylidene derivativesab

Entry X R1 R2 Time (min) Product Yield ()c MP (∘C)1 O H H 30 1a 94 168-1692 O H CH3 30 1b 92 158ndash1603 S H H 30 1c 95 142ndash1444 S CH3 H 30 1d 96 156-1575 S H CH3 30 1e 94 145ndash1476 NH H H 30 1f 87 88ndash907 O H H 60 2a 78 212-2138 O H CH3 60 2b 76 183ndash1859 S H H 60 2c 81 197-19810 S CH3 H 60 2d 77 170ndash17211 S H CH3 60 2e 83 177ndash17912 NH H H 60 2f 87 112ndash114aReaction conditions heteroarylaldehyde (1mmol) dimedone (2mmol) and DABCO (10mmol) in water (20mL) under reflux temperature bReactionconditions 1andashf (1mmol) malononitrile (2mmol) and DABCO (10mmol) in water (20mL) under reflux temperature cIsolated yields

XCHO

OO

O

O O

X

X

R2

R2

R1

R1DABCO H2O

Reflux 30min

=O S NHR1 and R2 = HCH3

2+

1(andashf)

Scheme 2

was monitored by TLC After completion of the reactionthe mixture was cooled to room temperature and the solidwas filtered off and washed with H

2O The crude product

was purified by column chromatographic technique usinghexane ethyl acetate

44 Spectral Data of Compounds

9-(Furan-2-yl)-3366-tetramethyl-345679-hexahydro-1H-xanthene-18(2H)-dione (1a) 1H NMR (400MHz CDCl

3) 120575

1014 (s 6H 2 times CH3) 1084 (s 6H 2 times CH

3) 2235 (s 4H

2 times CH2) 2425 (s 4H CH

2) 4941 (s 1H CH) 6159ndash6181

(m 2H Ar-H) 7133ndash7139 (d 1H Ar-H) IR 120584 3078 cmminus1(Ar-H) 2865 cmminus1 (Aliph CndashH) 1730 cmminus1 and 1673 cmminus1(C=O) 1602 cmminus1 (C=C) 1180 cmminus1 (CndashOndashC) Anal calcdfor C21H24O4 C 7409 H 711 found C 7403 H 707

3366-Tetramethyl-9-(5-methylfuran-2-yl)-345679-hexa-hydro-1H-xanthene-18(2H)-dione (1b) 1H NMR (400MHzCDCl

3) 120575 1039 (s 6H 2 timesCH

3) 1109 (s 6H 2 timesCH

3) 2109

(s 4H 2 timesCH2) 2551 (s 4H CH

2) 4832 (s 1H CH) 6108ndash

6226 (m 2H Ar-H) 3228 (s 3H Ar-CH3) IR 120584 3109 cmminus1

(Ar-H) 2905 cmminus1 (Alih CndashH) 1722 cmminus1 and 1688 cmminus1(C=O) 1630 cmminus1 (C=C) 1172 cmminus1 (CndashOndashC) Anal calcdfor C22H26O4 C 7455 H 739 found C 7528 H 688

3366-Tetramethyl-9-(thiophen-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-dione (1c) 1HNMR (400MHz CDCl

3)

120575 1208 (s 12H 4 timesCH3) 2109 (s 4H 2 timesCH

2) 2401 (s 4H

2 timesCH2) 4622 (s 1H CH) 6554 (d 1H Ar-H) 6828 (d 1H

Ar-H) 7298 (dd 1H Ar-H) IR 120584 3135 (Ar-H) 2920 cmminus1(Aliph CndashH) 1716 cmminus1 (C=O) 1648 cmminus1 and 1620 cmminus1(C=C) 1108 cmminus1 (CndashOndashC) Anal calcd for C

21H24O3S C

7075 H 679 S 899 found C 7133 H 628 S 849

3366-Tetramethyl-9-(3-methylthiophen-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-dione (1d) 1H NMR (400MHz CDCl

3) 120575 1100 (s 12H 4 times CH

3) 3035 (s 3H Ar-

CH3) 2281 (s 4H 2 times CH

2) 2544 (s 4H 2 times CH

2) 4875

(s 1H CH) 6478 (d 1H Ar-H) 6824 (d 1H Ar-H) IR120584 3042 cmminus1 (Ar-H) 2963 cmminus1 (CndashH) 1730 cmminus1 (C=O)1607 cmminus1 and 1588 cmminus1 (C=C) 1150 cmminus1 (CndashOndashC) Analcalcd for C

22H26O3S C 7132 H 707 S 865 found C 7128 H

709 S 869

3366-Tetramethyl-9-(5-methylthiophen-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-dione (1e) 1H NMR (400MHz CDCl

3) 120575 1288 (s 12H 4 times CH

3) 2988 (s 3H

Ar-CH3) 2448 (s 4H 2 times CH

2) 2722 (s 4H 2 times CH

2)

4658 (s 1H CH) 6234 (d 1H Ar-H) 6775 (d 1H Ar-H)IR 120584 3090 cmminus1 (Ar-H) 2882 cmminus1 (Aliph CndashH) 1716 cmminus1

4 ISRN Organic Chemistry

O

O O

X

CN

CN

2

O

X

CNNC CNNC

R2R2

R1R1

DABCO H2OReflux 30ndash60min+

2(andashf)1(andashf)

Scheme 3

OO OHOArH

O

DABCOOO

Ar O

HOKnoevenagel

O

O

Ar O O

O

Ar O

O

DABCOMichael addition

Cyclization

1st molecule

minusH2O

minusH2O

2nd molecule

B

A

1(andashf)

Scheme 4

(C=O) 1632 cmminus1 and 1610 cmminus1 (C=C) 1148 cmminus1 (CndashOndashC)Anal calcd for C

22H26O3S C 7132 H 707 S 865 found C

7154 H 768 S 914

3366-Tetramethyl-9-(1H-pyrrol-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-dione (1f) 1HNMR (400MHz CDCl

3)

120575 1018ndash1146 (m 12H 4 times CH3) 2154 (br s 8H 4 times CH

2

5601 (s 1H CH) 6957ndash6970 (s 1H Ar-H) 6698ndash6710 (d1H Ar-H) 6162 (dd 1H Ar-H) 9570 (br s 1H NH) IR120584 3397 cmminus1 3328 cmminus1 (NndashH) 3065 cmminus1 (Ar-H) 2978v(Aliph CndashH) 1680 cmminus1 (C=O) 1604 cmminus1 and 1469 cmminus1(C=C) 1145 cmminus1 (COC) Anal calcd for C

21H25NO3 C

7431 H 742 N 413 found C 7426 H 746 N 415

221015840-(3366-Tetramethyl-9-(furan-2-yl)-345679-hexa-hydro-1H-xanthene-18(2H)-diylidene)dimalononitrile (2a)1H NMR (400MHz CDCl

3) 120575 1016 (s 6H 2 times CH

3) 1128

(s 6H 2 times CH3) 2246 (s 4H 2 times CH

2) 2665 (s 4H CH

2)

4941 (s 1H CH) 6154ndash6188 (m 2H Ar-H) 7138ndash7144 (d1H Ar-H) IR 120584 3078 cmminus1 (Ar-H) 2865 cmminus1 (aliph CndashH)2224 cmminus1 (CN) 1716 cmminus1 and 1684 cmminus1 (C=O) 1620 cmminus1(C=C) 1154 cmminus1 (CndashOndashC) Anal calcd for C

27H24N4O2 C

7429 H 554 N 1284 found C 7382 H 569 N 1209

221015840-(3366-Tetramethyl-9-(5-methylfuran-2-yl)-345679-hexahydro-1H-xanthene-18(2H-diylidene)dimalononitrile(2b) 1H NMR (400MHz CDCl

3) 120575 0986 (s 6H 2 times CH

3)

1235 (s 6H 2 times CH3) 2244 (s 4H 2 times CH

2) 2658 (s

4H CH2) 4988 (s 1H CH) 6159ndash6181 (m 2H Ar-H)

3286 (s 3H Ar-CH3) IR 120584 3058 cmminus1 (Ar-H) 2944 cmminus1

(Aliph CndashH) 2224 cmminus1 (CN) 1714 cmminus1 and 1682 cmminus1(C=O) 1622 cmminus1 (C=C) 1144 cmminus1 (CndashOndashC) Anal calcdfor C28H26N4O2 C 7465 H 582 N 1244 found C 7511 H

608 N 1188

221015840-(3366-Tetramethyl-9-(thiophen-2-yl)-345679-hexa-hydro-1H-xanthene-18(2H)-diylidene)dimalononitrile (2c)1H NMR (400MHz CDCl

3) 120575 1029 (s 6H 2 times CH

3) 1208

(s 6H 2 times CH3) 2248 (s 4H 2 times CH

2) 2659 (s 4H CH

2)

4745 (s 1H CH) 6686ndash6789 (m 2H Ar-H) 7252ndash7263 (d1H Ar-H) IR 120584 3078 cmminus1 (Ar-H) 2988 cmminus1 (Aliph CndashH)2224 cmminus1 (CN) 1710 cmminus1 and 1688 cmminus1 (C=O) 1626 cmminus1(C=C) 1164 cmminus1 (CndashOndashC) Anal calcd for C

27H24N4OS C

7165 H 535 N 1284 S 709 found C 7118 H 574 N 1212 S783

221015840-(3366-Tetramethyl-9-(3-methylthiophen-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-diylidene)dimalononitrile(2d) 1H NMR (400MHz CDCl

3) 120575 1044 (s 6H 2 times CH

3)

1301 (s 6H 2 times CH3) 2144 (s 4H 2 times CH

2) 2656 (s

4H CH2) 4886 (s 1H CH) 6136ndash6172 (m 2H Ar-H)

3114 (s 3H Ar-CH3) IR 120584 3098 cmminus1 (Ar-H) 2898 cmminus1

(Aliph CndashH) 2224 cmminus1 (CN) 1710 cmminus1 and 1682 cmminus1(C=O) 1663 cmminus1 (C=C) 1156 cmminus1 (CndashOndashC) Anal calcd

ISRN Organic Chemistry 5

for C28H26N4OS C 7207 H 562 N 1201 S 687 found C

7112 H 528 N 1284 S 715

221015840-(3366-Tetramethyl-9-(5-methylthiophen-2-yl)- 345679-hexahydro-1H-xanthene-18(2H-diylidene)dimalononitrile(2e) 1H NMR (400MHz CDCl

3) 120575 1022 (s 6H 2 times CH

3)

1308 (s 6H 2 times CH3) 2224 (s 4H 2 times CH

2) 2538 (s

4H CH2) 4908 (s 1H CH) 6108ndash6191 (m 2H Ar-H)

3257 (s 3H Ar-CH3) IR 120584 3086 cmminus1 (Ar-H) 2910 cmminus1

(Aliph CndashH) 2224 cmminus1 (CN) 1728 cmminus1 and 1692 cmminus1(C=O) 1605 cmminus1 (C=C) 1162 cmminus1 (CndashOndashC) Anal calcdfor C28H26N4OS C 7207 H 562 N 1201 S 687 found C

7143 H 512 N 1277 S 725

221015840-(3366-Tetramethyl-9-(pyrrol-2-yl)-345679-hexahyd-ro-1H-xanthene-18(2H)-diylidene)dimalononitrile (2f) 1HNMR (400MHz CDCl

3) 120575 1022 (s 6H 2 times CH

3) 1063(s

6H 2 times CH3) 2268 (s 4H 2 times CH

2) 2569 (s 4H CH

2)

4858 (s 1H CH) 6168ndash6198 (m 2H Ar-H) 7124ndash7138 (d1H Ar-H) 8986 (br s 1H NH) IR 120584 3064 cmminus1 (Ar-H)2936 cmminus1 (Aliph CndashH) 2224 cmminus1 (CN) 1710 cmminus1 and1678 cmminus1 (C=O) 1619 cmminus1 (C=C) 1166 cmminus1 (COC) Analcalcd for C

21H24O4 C 7446 H 579 found C 7412 H 608

Acknowledgments

Theauthors are thankful to theDirector of SAIF IITMumbaifor spectral analysis and Dr Asutosh K Pandey Departmentof Engineering Chemistry Oriental University Indore (MP)for valuable suggestions

References

[1] R V A Orru and M De Greef ldquoRecent advances in solution-phase multicomponent methodology for the synthesis of hete-rocyclic compoundsrdquo Synthesis no 10 pp 1471ndash1499 2003

[2] A Domling ldquoRecent developments in isocyanide-based multi-component reactions in applied chemistryrdquo Chemical Reviewsvol 106 no 1 pp 17ndash89 2006

[3] A Domling and I Ugi ldquoMulticomponent reactions with iso-cyanidesrdquoAngewandte Chemie International Edition vol 39 no18 pp 3168ndash3210 2000

[4] J Peng W Hao X Wang S Tu N Ma and G ZhangldquoMicrowave-assisted synthesis of pyrazolo[43-f ]quinolin-7-one derivatives viamulti-component reactionsrdquoChinese Journalof Chemistry vol 27 no 9 pp 1707ndash1710 2009

[5] L F Tietze H Evers and E Topken ldquoA novel concept in com-binatorial chemistry in solution with the advantages of solid-phase synthesis formation of N-betaines by multicomponentdomino reactionsrdquo Angewandte Chemie International Editionvol 40 no 5 pp 903ndash905 2001

[6] T Masquelin H Bui B Brickley G Stephenson J Schw-erkoske and C Hulme ldquoSequential UgiStrecker reactionsvia microwave assisted organic synthesis novel 3-center-4-component and 3-center-5-component multi-component reac-tionsrdquo Tetrahedron Letters vol 47 no 17 pp 2989ndash2991 2006

[7] A Djande M Kiendrebeogo M Compaore et al ldquoAntioxidantpotential of 4-acyl isochroman-1 3-dionesrdquo Research Journal ofChemical Sciences vol 1 no 5 pp 88ndash90 2011

[8] S M Menchen S C Benson J Y L Lam et al Patent US6583168 2003

[9] C G Knight and T Stephens ldquoXanthene-dye-labelled phos-phatidylethanolamines as probes of interfacial pH Studies inphospholipid vesiclesrdquo Biochemical Journal vol 258 no 3 pp683ndash689 1989

[10] A K Bhattacharya and K C Rana ldquoMicrowave-assisted syn-thesis of 14-aryl-14H-dibenzo[aj]xanthenes catalysed by pTSAin solution and solvent-free conditionsrdquo Mendeleev Communi-cations vol 17 no 4 pp 247ndash248 2007

[11] G Mulongo J Mbabazi B Odongkara H Twinomuhwezi andG B Mpango ldquoNew biologically active compounds from 1 3-diketonesrdquo Research Journal of Chemical Sciences vol 1 no 3pp 102ndash108 2011

[12] Z Karimi-Jaberi and M M Hashemi ldquoOne step synthesisof 14-alkyl- or aryl-14H-dibenzo[aj]xanthenes using sodiumhydrogen sulfate as catalystrdquo Monatshefte fur Chemie vol 139no 6 pp 605ndash608 2008

[13] M Seyyedhamzeh P Mirzaei and A Bazgir ldquoSolvent-freesynthesis of aryl-14H-dibenzo[aj]xanthenes and 18-dioxo-octahydro-xanthenes using silica sulfuric acid as catalystrdquoDyesand Pigments vol 76 no 3 pp 836ndash839 2008

[14] J QWang and R G Harvey ldquoSynthesis of polycyclic xanthenesand furans via palladium-catalyzed cyclization of polycyclicaryltriflate estersrdquo Tetrahedron vol 58 no 29 pp 5927ndash59312002

[15] G Casiraghi G Casnati M Catellani and M A A CorinaldquoConvenient one-step synthesis of xanthene derivativesrdquo Syn-thesis no 8 pp 564ndash564 1974

[16] S Gupta P Gupta A Sachar and R L Sharma ldquoSyntheticstudies of some varied structural systems of biologically potentpolynitrogen heteropolycyclicsrdquo Indian Journal of Chemistry Bvol 49 no 9 pp 1243ndash1256 2010

[17] M H Majid A Hamideh B Khadijeh S Mina A O Hosseinand F B Fatemeh ldquoSolvent-free synthesis of xanthenes deriva-tives by preyssler type heteropolyacidrdquo Bulletin of ChemicalSociety of Ethiopia vol 25 no 3 pp 399ndash406 2011

[18] K Muharrem ldquoAldol condensation and michael addition of4 4-dimethylcyclohexane-1 3-dione and aromatic aldehydesUnconventional substituent effectsrdquo Chinese Journal of Chem-istry vol 29 no 11 pp 2355ndash2360 2011

[19] A Ilangovan S Malayappasamy S Muralidharan and SMaruthamuthu ldquoA highly efficient green synthesis of 1 8-dioxooctahydroxanthenesrdquo Chemistry Central Journal vol 5pp 81ndash86 2011

[20] B Baghernejad ldquo4-Diazabicyclo [222] octane (DABCO) asa useful catalyst in organic synthesisrdquo European Journal ofChemistry vol 1 no 1 pp 54ndash60 2010

[21] H Yang R Tian and Y Li ldquoOrganic reactions catalyzed by 14-diazabicyclo [222] octane (DABCO)rdquo Frontiers of Chemistryin China vol 3 no 3 pp 279ndash287 2008

[22] X Da-Zhen Y Liu S Shi and Y Wang ldquoA simple efficientand green procedure for Knoevenagel condensation catalyzedby [C

4dabco][BF

4] ionic liquid in waterrdquo Green Chemistry vol

12 no 3 pp 514ndash517 2010[23] M Bigdeli ldquoClean synthesis of 18-dioxooctahydroxanthenes

promoted by DABCO-bromine in aqueous mediardquo ChineseChemical Letters vol 21 no 10 pp 1180ndash1182 2010

[24] B Saeed R Sorour B Morteza and H G Jurgen ldquoDABCO-catalyzed efficient synthesis of naphthopyran derivatives viaone-pot three-component condensation reaction at room tem-peraturerdquo Synthetic Communications vol 38 no 7 pp 1078ndash1089 2008

6 ISRN Organic Chemistry

[25] K Y Lee J M Kim and J N Kim ldquoSynthesis of 2344a-tet-tetrahydroxanthenrahydroxanthen-1-ones and 33a-dihydro-2H-cyclopenta[b]chromen-1-ones from the reaction of salicy-laldehydes and 2-cyclohexen-1-one and 2-cyclopenten-1-onerdquoBulletin of the Korean Chemical Society vol 24 no 1 pp 17ndash182003

[26] S Jain G N Babu S R Jetti S Harshada andD SuryaprakashldquoSynthesis antitubercular and antifungal activities of heteroaryl-substituted oxirance derived from Baylis-Hillman adductsrdquoMedicinal Chemistry Research vol 21 no 10 pp 2744ndash27482012

[27] S Jain P Paliwal and G N Babu ldquoDABCO promoted one-pot synthesis of dihydro pyrano(c) chromene and pyrano[2 3-d]pyrimidine derivatives and their biological activitiesrdquo Journalof Saudi Chemical Society 2011

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Inorganic ChemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

International Journal ofPhotoenergy

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Carbohydrate Chemistry

International Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Advances in

Physical Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom

Analytical Methods in Chemistry

Journal of

Volume 2014

Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

SpectroscopyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Medicinal ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Chromatography Research International

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Applied ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Theoretical ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Spectroscopy

Analytical ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Quantum Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Organic Chemistry International

ElectrochemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

CatalystsJournal of

4 ISRN Organic Chemistry

O

O O

X

CN

CN

2

O

X

CNNC CNNC

R2R2

R1R1

DABCO H2OReflux 30ndash60min+

2(andashf)1(andashf)

Scheme 3

OO OHOArH

O

DABCOOO

Ar O

HOKnoevenagel

O

O

Ar O O

O

Ar O

O

DABCOMichael addition

Cyclization

1st molecule

minusH2O

minusH2O

2nd molecule

B

A

1(andashf)

Scheme 4

(C=O) 1632 cmminus1 and 1610 cmminus1 (C=C) 1148 cmminus1 (CndashOndashC)Anal calcd for C

22H26O3S C 7132 H 707 S 865 found C

7154 H 768 S 914

3366-Tetramethyl-9-(1H-pyrrol-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-dione (1f) 1HNMR (400MHz CDCl

3)

120575 1018ndash1146 (m 12H 4 times CH3) 2154 (br s 8H 4 times CH

2

5601 (s 1H CH) 6957ndash6970 (s 1H Ar-H) 6698ndash6710 (d1H Ar-H) 6162 (dd 1H Ar-H) 9570 (br s 1H NH) IR120584 3397 cmminus1 3328 cmminus1 (NndashH) 3065 cmminus1 (Ar-H) 2978v(Aliph CndashH) 1680 cmminus1 (C=O) 1604 cmminus1 and 1469 cmminus1(C=C) 1145 cmminus1 (COC) Anal calcd for C

21H25NO3 C

7431 H 742 N 413 found C 7426 H 746 N 415

221015840-(3366-Tetramethyl-9-(furan-2-yl)-345679-hexa-hydro-1H-xanthene-18(2H)-diylidene)dimalononitrile (2a)1H NMR (400MHz CDCl

3) 120575 1016 (s 6H 2 times CH

3) 1128

(s 6H 2 times CH3) 2246 (s 4H 2 times CH

2) 2665 (s 4H CH

2)

4941 (s 1H CH) 6154ndash6188 (m 2H Ar-H) 7138ndash7144 (d1H Ar-H) IR 120584 3078 cmminus1 (Ar-H) 2865 cmminus1 (aliph CndashH)2224 cmminus1 (CN) 1716 cmminus1 and 1684 cmminus1 (C=O) 1620 cmminus1(C=C) 1154 cmminus1 (CndashOndashC) Anal calcd for C

27H24N4O2 C

7429 H 554 N 1284 found C 7382 H 569 N 1209

221015840-(3366-Tetramethyl-9-(5-methylfuran-2-yl)-345679-hexahydro-1H-xanthene-18(2H-diylidene)dimalononitrile(2b) 1H NMR (400MHz CDCl

3) 120575 0986 (s 6H 2 times CH

3)

1235 (s 6H 2 times CH3) 2244 (s 4H 2 times CH

2) 2658 (s

4H CH2) 4988 (s 1H CH) 6159ndash6181 (m 2H Ar-H)

3286 (s 3H Ar-CH3) IR 120584 3058 cmminus1 (Ar-H) 2944 cmminus1

(Aliph CndashH) 2224 cmminus1 (CN) 1714 cmminus1 and 1682 cmminus1(C=O) 1622 cmminus1 (C=C) 1144 cmminus1 (CndashOndashC) Anal calcdfor C28H26N4O2 C 7465 H 582 N 1244 found C 7511 H

608 N 1188

221015840-(3366-Tetramethyl-9-(thiophen-2-yl)-345679-hexa-hydro-1H-xanthene-18(2H)-diylidene)dimalononitrile (2c)1H NMR (400MHz CDCl

3) 120575 1029 (s 6H 2 times CH

3) 1208

(s 6H 2 times CH3) 2248 (s 4H 2 times CH

2) 2659 (s 4H CH

2)

4745 (s 1H CH) 6686ndash6789 (m 2H Ar-H) 7252ndash7263 (d1H Ar-H) IR 120584 3078 cmminus1 (Ar-H) 2988 cmminus1 (Aliph CndashH)2224 cmminus1 (CN) 1710 cmminus1 and 1688 cmminus1 (C=O) 1626 cmminus1(C=C) 1164 cmminus1 (CndashOndashC) Anal calcd for C

27H24N4OS C

7165 H 535 N 1284 S 709 found C 7118 H 574 N 1212 S783

221015840-(3366-Tetramethyl-9-(3-methylthiophen-2-yl)-345679-hexahydro-1H-xanthene-18(2H)-diylidene)dimalononitrile(2d) 1H NMR (400MHz CDCl

3) 120575 1044 (s 6H 2 times CH

3)

1301 (s 6H 2 times CH3) 2144 (s 4H 2 times CH

2) 2656 (s

4H CH2) 4886 (s 1H CH) 6136ndash6172 (m 2H Ar-H)

3114 (s 3H Ar-CH3) IR 120584 3098 cmminus1 (Ar-H) 2898 cmminus1

(Aliph CndashH) 2224 cmminus1 (CN) 1710 cmminus1 and 1682 cmminus1(C=O) 1663 cmminus1 (C=C) 1156 cmminus1 (CndashOndashC) Anal calcd

ISRN Organic Chemistry 5

for C28H26N4OS C 7207 H 562 N 1201 S 687 found C

7112 H 528 N 1284 S 715

221015840-(3366-Tetramethyl-9-(5-methylthiophen-2-yl)- 345679-hexahydro-1H-xanthene-18(2H-diylidene)dimalononitrile(2e) 1H NMR (400MHz CDCl

3) 120575 1022 (s 6H 2 times CH

3)

1308 (s 6H 2 times CH3) 2224 (s 4H 2 times CH

2) 2538 (s

4H CH2) 4908 (s 1H CH) 6108ndash6191 (m 2H Ar-H)

3257 (s 3H Ar-CH3) IR 120584 3086 cmminus1 (Ar-H) 2910 cmminus1

(Aliph CndashH) 2224 cmminus1 (CN) 1728 cmminus1 and 1692 cmminus1(C=O) 1605 cmminus1 (C=C) 1162 cmminus1 (CndashOndashC) Anal calcdfor C28H26N4OS C 7207 H 562 N 1201 S 687 found C

7143 H 512 N 1277 S 725

221015840-(3366-Tetramethyl-9-(pyrrol-2-yl)-345679-hexahyd-ro-1H-xanthene-18(2H)-diylidene)dimalononitrile (2f) 1HNMR (400MHz CDCl

3) 120575 1022 (s 6H 2 times CH

3) 1063(s

6H 2 times CH3) 2268 (s 4H 2 times CH

2) 2569 (s 4H CH

2)

4858 (s 1H CH) 6168ndash6198 (m 2H Ar-H) 7124ndash7138 (d1H Ar-H) 8986 (br s 1H NH) IR 120584 3064 cmminus1 (Ar-H)2936 cmminus1 (Aliph CndashH) 2224 cmminus1 (CN) 1710 cmminus1 and1678 cmminus1 (C=O) 1619 cmminus1 (C=C) 1166 cmminus1 (COC) Analcalcd for C

21H24O4 C 7446 H 579 found C 7412 H 608

Acknowledgments

Theauthors are thankful to theDirector of SAIF IITMumbaifor spectral analysis and Dr Asutosh K Pandey Departmentof Engineering Chemistry Oriental University Indore (MP)for valuable suggestions

References

[1] R V A Orru and M De Greef ldquoRecent advances in solution-phase multicomponent methodology for the synthesis of hete-rocyclic compoundsrdquo Synthesis no 10 pp 1471ndash1499 2003

[2] A Domling ldquoRecent developments in isocyanide-based multi-component reactions in applied chemistryrdquo Chemical Reviewsvol 106 no 1 pp 17ndash89 2006

[3] A Domling and I Ugi ldquoMulticomponent reactions with iso-cyanidesrdquoAngewandte Chemie International Edition vol 39 no18 pp 3168ndash3210 2000

[4] J Peng W Hao X Wang S Tu N Ma and G ZhangldquoMicrowave-assisted synthesis of pyrazolo[43-f ]quinolin-7-one derivatives viamulti-component reactionsrdquoChinese Journalof Chemistry vol 27 no 9 pp 1707ndash1710 2009

[5] L F Tietze H Evers and E Topken ldquoA novel concept in com-binatorial chemistry in solution with the advantages of solid-phase synthesis formation of N-betaines by multicomponentdomino reactionsrdquo Angewandte Chemie International Editionvol 40 no 5 pp 903ndash905 2001

[6] T Masquelin H Bui B Brickley G Stephenson J Schw-erkoske and C Hulme ldquoSequential UgiStrecker reactionsvia microwave assisted organic synthesis novel 3-center-4-component and 3-center-5-component multi-component reac-tionsrdquo Tetrahedron Letters vol 47 no 17 pp 2989ndash2991 2006

[7] A Djande M Kiendrebeogo M Compaore et al ldquoAntioxidantpotential of 4-acyl isochroman-1 3-dionesrdquo Research Journal ofChemical Sciences vol 1 no 5 pp 88ndash90 2011

[8] S M Menchen S C Benson J Y L Lam et al Patent US6583168 2003

[9] C G Knight and T Stephens ldquoXanthene-dye-labelled phos-phatidylethanolamines as probes of interfacial pH Studies inphospholipid vesiclesrdquo Biochemical Journal vol 258 no 3 pp683ndash689 1989

[10] A K Bhattacharya and K C Rana ldquoMicrowave-assisted syn-thesis of 14-aryl-14H-dibenzo[aj]xanthenes catalysed by pTSAin solution and solvent-free conditionsrdquo Mendeleev Communi-cations vol 17 no 4 pp 247ndash248 2007

[11] G Mulongo J Mbabazi B Odongkara H Twinomuhwezi andG B Mpango ldquoNew biologically active compounds from 1 3-diketonesrdquo Research Journal of Chemical Sciences vol 1 no 3pp 102ndash108 2011

[12] Z Karimi-Jaberi and M M Hashemi ldquoOne step synthesisof 14-alkyl- or aryl-14H-dibenzo[aj]xanthenes using sodiumhydrogen sulfate as catalystrdquo Monatshefte fur Chemie vol 139no 6 pp 605ndash608 2008

[13] M Seyyedhamzeh P Mirzaei and A Bazgir ldquoSolvent-freesynthesis of aryl-14H-dibenzo[aj]xanthenes and 18-dioxo-octahydro-xanthenes using silica sulfuric acid as catalystrdquoDyesand Pigments vol 76 no 3 pp 836ndash839 2008

[14] J QWang and R G Harvey ldquoSynthesis of polycyclic xanthenesand furans via palladium-catalyzed cyclization of polycyclicaryltriflate estersrdquo Tetrahedron vol 58 no 29 pp 5927ndash59312002

[15] G Casiraghi G Casnati M Catellani and M A A CorinaldquoConvenient one-step synthesis of xanthene derivativesrdquo Syn-thesis no 8 pp 564ndash564 1974

[16] S Gupta P Gupta A Sachar and R L Sharma ldquoSyntheticstudies of some varied structural systems of biologically potentpolynitrogen heteropolycyclicsrdquo Indian Journal of Chemistry Bvol 49 no 9 pp 1243ndash1256 2010

[17] M H Majid A Hamideh B Khadijeh S Mina A O Hosseinand F B Fatemeh ldquoSolvent-free synthesis of xanthenes deriva-tives by preyssler type heteropolyacidrdquo Bulletin of ChemicalSociety of Ethiopia vol 25 no 3 pp 399ndash406 2011

[18] K Muharrem ldquoAldol condensation and michael addition of4 4-dimethylcyclohexane-1 3-dione and aromatic aldehydesUnconventional substituent effectsrdquo Chinese Journal of Chem-istry vol 29 no 11 pp 2355ndash2360 2011

[19] A Ilangovan S Malayappasamy S Muralidharan and SMaruthamuthu ldquoA highly efficient green synthesis of 1 8-dioxooctahydroxanthenesrdquo Chemistry Central Journal vol 5pp 81ndash86 2011

[20] B Baghernejad ldquo4-Diazabicyclo [222] octane (DABCO) asa useful catalyst in organic synthesisrdquo European Journal ofChemistry vol 1 no 1 pp 54ndash60 2010

[21] H Yang R Tian and Y Li ldquoOrganic reactions catalyzed by 14-diazabicyclo [222] octane (DABCO)rdquo Frontiers of Chemistryin China vol 3 no 3 pp 279ndash287 2008

[22] X Da-Zhen Y Liu S Shi and Y Wang ldquoA simple efficientand green procedure for Knoevenagel condensation catalyzedby [C

4dabco][BF

4] ionic liquid in waterrdquo Green Chemistry vol

12 no 3 pp 514ndash517 2010[23] M Bigdeli ldquoClean synthesis of 18-dioxooctahydroxanthenes

promoted by DABCO-bromine in aqueous mediardquo ChineseChemical Letters vol 21 no 10 pp 1180ndash1182 2010

[24] B Saeed R Sorour B Morteza and H G Jurgen ldquoDABCO-catalyzed efficient synthesis of naphthopyran derivatives viaone-pot three-component condensation reaction at room tem-peraturerdquo Synthetic Communications vol 38 no 7 pp 1078ndash1089 2008

6 ISRN Organic Chemistry

[25] K Y Lee J M Kim and J N Kim ldquoSynthesis of 2344a-tet-tetrahydroxanthenrahydroxanthen-1-ones and 33a-dihydro-2H-cyclopenta[b]chromen-1-ones from the reaction of salicy-laldehydes and 2-cyclohexen-1-one and 2-cyclopenten-1-onerdquoBulletin of the Korean Chemical Society vol 24 no 1 pp 17ndash182003

[26] S Jain G N Babu S R Jetti S Harshada andD SuryaprakashldquoSynthesis antitubercular and antifungal activities of heteroaryl-substituted oxirance derived from Baylis-Hillman adductsrdquoMedicinal Chemistry Research vol 21 no 10 pp 2744ndash27482012

[27] S Jain P Paliwal and G N Babu ldquoDABCO promoted one-pot synthesis of dihydro pyrano(c) chromene and pyrano[2 3-d]pyrimidine derivatives and their biological activitiesrdquo Journalof Saudi Chemical Society 2011

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Inorganic ChemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

International Journal ofPhotoenergy

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Carbohydrate Chemistry

International Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Advances in

Physical Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom

Analytical Methods in Chemistry

Journal of

Volume 2014

Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

SpectroscopyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Medicinal ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Chromatography Research International

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Applied ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Theoretical ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Spectroscopy

Analytical ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Quantum Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Organic Chemistry International

ElectrochemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

CatalystsJournal of

ISRN Organic Chemistry 5

for C28H26N4OS C 7207 H 562 N 1201 S 687 found C

7112 H 528 N 1284 S 715

221015840-(3366-Tetramethyl-9-(5-methylthiophen-2-yl)- 345679-hexahydro-1H-xanthene-18(2H-diylidene)dimalononitrile(2e) 1H NMR (400MHz CDCl

3) 120575 1022 (s 6H 2 times CH

3)

1308 (s 6H 2 times CH3) 2224 (s 4H 2 times CH

2) 2538 (s

4H CH2) 4908 (s 1H CH) 6108ndash6191 (m 2H Ar-H)

3257 (s 3H Ar-CH3) IR 120584 3086 cmminus1 (Ar-H) 2910 cmminus1

(Aliph CndashH) 2224 cmminus1 (CN) 1728 cmminus1 and 1692 cmminus1(C=O) 1605 cmminus1 (C=C) 1162 cmminus1 (CndashOndashC) Anal calcdfor C28H26N4OS C 7207 H 562 N 1201 S 687 found C

7143 H 512 N 1277 S 725

221015840-(3366-Tetramethyl-9-(pyrrol-2-yl)-345679-hexahyd-ro-1H-xanthene-18(2H)-diylidene)dimalononitrile (2f) 1HNMR (400MHz CDCl

3) 120575 1022 (s 6H 2 times CH

3) 1063(s

6H 2 times CH3) 2268 (s 4H 2 times CH

2) 2569 (s 4H CH

2)

4858 (s 1H CH) 6168ndash6198 (m 2H Ar-H) 7124ndash7138 (d1H Ar-H) 8986 (br s 1H NH) IR 120584 3064 cmminus1 (Ar-H)2936 cmminus1 (Aliph CndashH) 2224 cmminus1 (CN) 1710 cmminus1 and1678 cmminus1 (C=O) 1619 cmminus1 (C=C) 1166 cmminus1 (COC) Analcalcd for C

21H24O4 C 7446 H 579 found C 7412 H 608

Acknowledgments

Theauthors are thankful to theDirector of SAIF IITMumbaifor spectral analysis and Dr Asutosh K Pandey Departmentof Engineering Chemistry Oriental University Indore (MP)for valuable suggestions

References

[1] R V A Orru and M De Greef ldquoRecent advances in solution-phase multicomponent methodology for the synthesis of hete-rocyclic compoundsrdquo Synthesis no 10 pp 1471ndash1499 2003

[2] A Domling ldquoRecent developments in isocyanide-based multi-component reactions in applied chemistryrdquo Chemical Reviewsvol 106 no 1 pp 17ndash89 2006

[3] A Domling and I Ugi ldquoMulticomponent reactions with iso-cyanidesrdquoAngewandte Chemie International Edition vol 39 no18 pp 3168ndash3210 2000

[4] J Peng W Hao X Wang S Tu N Ma and G ZhangldquoMicrowave-assisted synthesis of pyrazolo[43-f ]quinolin-7-one derivatives viamulti-component reactionsrdquoChinese Journalof Chemistry vol 27 no 9 pp 1707ndash1710 2009

[5] L F Tietze H Evers and E Topken ldquoA novel concept in com-binatorial chemistry in solution with the advantages of solid-phase synthesis formation of N-betaines by multicomponentdomino reactionsrdquo Angewandte Chemie International Editionvol 40 no 5 pp 903ndash905 2001

[6] T Masquelin H Bui B Brickley G Stephenson J Schw-erkoske and C Hulme ldquoSequential UgiStrecker reactionsvia microwave assisted organic synthesis novel 3-center-4-component and 3-center-5-component multi-component reac-tionsrdquo Tetrahedron Letters vol 47 no 17 pp 2989ndash2991 2006

[7] A Djande M Kiendrebeogo M Compaore et al ldquoAntioxidantpotential of 4-acyl isochroman-1 3-dionesrdquo Research Journal ofChemical Sciences vol 1 no 5 pp 88ndash90 2011

[8] S M Menchen S C Benson J Y L Lam et al Patent US6583168 2003

[9] C G Knight and T Stephens ldquoXanthene-dye-labelled phos-phatidylethanolamines as probes of interfacial pH Studies inphospholipid vesiclesrdquo Biochemical Journal vol 258 no 3 pp683ndash689 1989

[10] A K Bhattacharya and K C Rana ldquoMicrowave-assisted syn-thesis of 14-aryl-14H-dibenzo[aj]xanthenes catalysed by pTSAin solution and solvent-free conditionsrdquo Mendeleev Communi-cations vol 17 no 4 pp 247ndash248 2007

[11] G Mulongo J Mbabazi B Odongkara H Twinomuhwezi andG B Mpango ldquoNew biologically active compounds from 1 3-diketonesrdquo Research Journal of Chemical Sciences vol 1 no 3pp 102ndash108 2011

[12] Z Karimi-Jaberi and M M Hashemi ldquoOne step synthesisof 14-alkyl- or aryl-14H-dibenzo[aj]xanthenes using sodiumhydrogen sulfate as catalystrdquo Monatshefte fur Chemie vol 139no 6 pp 605ndash608 2008

[13] M Seyyedhamzeh P Mirzaei and A Bazgir ldquoSolvent-freesynthesis of aryl-14H-dibenzo[aj]xanthenes and 18-dioxo-octahydro-xanthenes using silica sulfuric acid as catalystrdquoDyesand Pigments vol 76 no 3 pp 836ndash839 2008

[14] J QWang and R G Harvey ldquoSynthesis of polycyclic xanthenesand furans via palladium-catalyzed cyclization of polycyclicaryltriflate estersrdquo Tetrahedron vol 58 no 29 pp 5927ndash59312002

[15] G Casiraghi G Casnati M Catellani and M A A CorinaldquoConvenient one-step synthesis of xanthene derivativesrdquo Syn-thesis no 8 pp 564ndash564 1974

[16] S Gupta P Gupta A Sachar and R L Sharma ldquoSyntheticstudies of some varied structural systems of biologically potentpolynitrogen heteropolycyclicsrdquo Indian Journal of Chemistry Bvol 49 no 9 pp 1243ndash1256 2010

[17] M H Majid A Hamideh B Khadijeh S Mina A O Hosseinand F B Fatemeh ldquoSolvent-free synthesis of xanthenes deriva-tives by preyssler type heteropolyacidrdquo Bulletin of ChemicalSociety of Ethiopia vol 25 no 3 pp 399ndash406 2011

[18] K Muharrem ldquoAldol condensation and michael addition of4 4-dimethylcyclohexane-1 3-dione and aromatic aldehydesUnconventional substituent effectsrdquo Chinese Journal of Chem-istry vol 29 no 11 pp 2355ndash2360 2011

[19] A Ilangovan S Malayappasamy S Muralidharan and SMaruthamuthu ldquoA highly efficient green synthesis of 1 8-dioxooctahydroxanthenesrdquo Chemistry Central Journal vol 5pp 81ndash86 2011

[20] B Baghernejad ldquo4-Diazabicyclo [222] octane (DABCO) asa useful catalyst in organic synthesisrdquo European Journal ofChemistry vol 1 no 1 pp 54ndash60 2010

[21] H Yang R Tian and Y Li ldquoOrganic reactions catalyzed by 14-diazabicyclo [222] octane (DABCO)rdquo Frontiers of Chemistryin China vol 3 no 3 pp 279ndash287 2008

[22] X Da-Zhen Y Liu S Shi and Y Wang ldquoA simple efficientand green procedure for Knoevenagel condensation catalyzedby [C

4dabco][BF

4] ionic liquid in waterrdquo Green Chemistry vol

12 no 3 pp 514ndash517 2010[23] M Bigdeli ldquoClean synthesis of 18-dioxooctahydroxanthenes

promoted by DABCO-bromine in aqueous mediardquo ChineseChemical Letters vol 21 no 10 pp 1180ndash1182 2010

[24] B Saeed R Sorour B Morteza and H G Jurgen ldquoDABCO-catalyzed efficient synthesis of naphthopyran derivatives viaone-pot three-component condensation reaction at room tem-peraturerdquo Synthetic Communications vol 38 no 7 pp 1078ndash1089 2008

6 ISRN Organic Chemistry

[25] K Y Lee J M Kim and J N Kim ldquoSynthesis of 2344a-tet-tetrahydroxanthenrahydroxanthen-1-ones and 33a-dihydro-2H-cyclopenta[b]chromen-1-ones from the reaction of salicy-laldehydes and 2-cyclohexen-1-one and 2-cyclopenten-1-onerdquoBulletin of the Korean Chemical Society vol 24 no 1 pp 17ndash182003

[26] S Jain G N Babu S R Jetti S Harshada andD SuryaprakashldquoSynthesis antitubercular and antifungal activities of heteroaryl-substituted oxirance derived from Baylis-Hillman adductsrdquoMedicinal Chemistry Research vol 21 no 10 pp 2744ndash27482012

[27] S Jain P Paliwal and G N Babu ldquoDABCO promoted one-pot synthesis of dihydro pyrano(c) chromene and pyrano[2 3-d]pyrimidine derivatives and their biological activitiesrdquo Journalof Saudi Chemical Society 2011

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Inorganic ChemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

International Journal ofPhotoenergy

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Carbohydrate Chemistry

International Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Advances in

Physical Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom

Analytical Methods in Chemistry

Journal of

Volume 2014

Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

SpectroscopyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Medicinal ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Chromatography Research International

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Applied ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Theoretical ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Spectroscopy

Analytical ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Quantum Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Organic Chemistry International

ElectrochemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

CatalystsJournal of

6 ISRN Organic Chemistry

[25] K Y Lee J M Kim and J N Kim ldquoSynthesis of 2344a-tet-tetrahydroxanthenrahydroxanthen-1-ones and 33a-dihydro-2H-cyclopenta[b]chromen-1-ones from the reaction of salicy-laldehydes and 2-cyclohexen-1-one and 2-cyclopenten-1-onerdquoBulletin of the Korean Chemical Society vol 24 no 1 pp 17ndash182003

[26] S Jain G N Babu S R Jetti S Harshada andD SuryaprakashldquoSynthesis antitubercular and antifungal activities of heteroaryl-substituted oxirance derived from Baylis-Hillman adductsrdquoMedicinal Chemistry Research vol 21 no 10 pp 2744ndash27482012

[27] S Jain P Paliwal and G N Babu ldquoDABCO promoted one-pot synthesis of dihydro pyrano(c) chromene and pyrano[2 3-d]pyrimidine derivatives and their biological activitiesrdquo Journalof Saudi Chemical Society 2011

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Inorganic ChemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

International Journal ofPhotoenergy

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Carbohydrate Chemistry

International Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Advances in

Physical Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom

Analytical Methods in Chemistry

Journal of

Volume 2014

Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

SpectroscopyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Medicinal ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Chromatography Research International

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Applied ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Theoretical ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Spectroscopy

Analytical ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Quantum Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Organic Chemistry International

ElectrochemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

CatalystsJournal of

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Inorganic ChemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

International Journal ofPhotoenergy

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Carbohydrate Chemistry

International Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Advances in

Physical Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom

Analytical Methods in Chemistry

Journal of

Volume 2014

Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

SpectroscopyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Medicinal ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Chromatography Research International

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Applied ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Theoretical ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Spectroscopy

Analytical ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Quantum Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Organic Chemistry International

ElectrochemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

CatalystsJournal of