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International Journal of Materials Science
ISSN 0973-4589 Volume 13, Number 3 (2018), pp. 189-204
© Research India Publications
http://www.ripublication.com
A Hantzsch condensation reaction / Dihydropyridine
Cascade Synthesis on Zeolite substrate
Adya Jain*, Shikha Singh, Kautily Rao Tiwari,
Neeraj Kumar and Radha Tomar
S. O. S in Chemistry, Jiwaji University, Gwalior, M.P., 474011, India.
Graphical Abstract:
Fig 1: Graphical Abstract
Abstract
Competence of Nanoporous Modified Zeolite-Beta has been observed at
various parameters (i.e. different solvent, temperature, catalyst concentration
and time interval) on the yield of different derivatives. Synthesis of 9, 10-
Diarylacridine-1, 8-dione was carried out by single-pot Hantzsch condensation
190 Adya Jain et al
reaction, which includes three component reactants i.e. aldehyde, amine and 5,
5-Dimethyl-1, 3- cyclohexanedione (dimedone). Expeditious with excellent
Yield of synthesized drug intermediates from Cr2O3-H-β was found to be
88.75% in ethanol at 90ºC. The synthesized zeolites sample were
characterized by the help of Fourier transform infrared spectroscopy (FTIR),
X-Ray diffraction (XRD), BET Surface Area and Porosity and Scanning
electron microscopy (SEM) while the synthesis of drug derivatives were
confirmed by Fourier transform infrared spectroscopy (FTIR), 1H-Nuclear
Magnetic Resonance Spectroscopy (1H-NMR) and Liquid chromatography-
Mass spectrometer (LC-MS).
Keywords: Zeolite Beta, Hantzsch condensation, 9, 10-Diarylacridine-1, 8-
dione
1. INTRODUCTION
Dihydropyridine (DHP) derivatives (i.e. Acridinediones, Quinolines) displays wide
array of biological activities such as vasodilator, anti-atherosclerotic, antitumor,
antidiabetic [1] calcium β-blockers, antihypertensive activity, α1a-antagonists and
heart defibrillation. Acridine derivatives possess number of biological activities i.e.
antitumor [2], cytotoxic, anticancer [3], antimicrobial, anti multidrug resistant,
fungicidal, antibacterial activity, antiglucoma [4], mutagenic properties etc.
Dihydopyridine molecules are synthesized by one pot multicomponent condensation
reaction i.e. Hantzsch Condensation Reaction which is a catalytic driven reaction. In
the absence of catalyst, the obtained yield percentage is unsatisfactorily in lower
amount and the reaction completes in long duration.
NH
Dihydropyridine
N
O O
CH3CH3
CH3
CH3
R
R1
Acridine-1,8-diones
NH
CH3
OO Ar
OEt
Quinazoline
Fig 2: Structures representing Parent Nucleus Molecule and Drug Derivatives
A number of different derivates of Acridinedione and Quinolines has been
synthesized by different methods in the presence of different catalysts and solvents
such as alumina (neutral or basic) as mineral solid supports using DMF as solvent [5],
p-dodecylbenezenesulfonic acid (DBSA) as a Bronsted acid-surfactant-combined
catalyst [6], Amberlyst-15 in CH3CN [7], 1-butyl-3-methyl-imidazolium
tetrafluoroborate ([bmim][BF4]) [8], tris(pentafluorophenyl) borane [B(C6F5)3] [9], L-
proline [10], sodium 1-dodecanesulfonate (SDS) [11], Brønsted acidic imidazolium
salts containing perfluoroalkyl tails [12] Hf(NPf2)4 [13], nano-Fe3O4 [14], Cross-
dehydrogenative regioselective Csp3–Csp2 coupling of enamino-ketones [15],
A Hantzsch condensation reaction / Dihydropyridine Cascade Synthesis on Zeolite substrate 191
[Bmim]ClO4 [16], aluminium dodecyl sulfate trihydrate [Al(DS)3].3H2O a Lewis
acid-surfactant-combined catalyst[17], magnetite (Fe3O4)/chitosan as a magnetically
recyclable heterogeneous nanocatalyst[18], P2O5 [19], ionic liquid triethylamine
hydrogen sulphate [Et3N]+ [HSO4]- [20], monodisperse platinum nanoparticles
supported with reduced graphene oxide[21] etc. Modified/Simple Zeolite are not used
as catalyst for Hantzsch condensation reaction till date.
Some commercial drugs of 1, 4 Dihydropyridine
NH
OCH3
N+
O-
O
O
O
CH3
O
CH3CH3
NH
OCH3
Cl
O
O
CH3
O
CH3CH3
Cl
NH
OCH3
O
O
CH3
O
CH3CH3
N+
O-
O
Nifadipine(1) Felodipine(2) Nitrendipine(3)
Fig. 3: Structure of Nifadipine(1), Felodipine(2) and Nitrendipine(3)
Calcium Channel Blocker
Dihydropyridines
First Generation
Nifedipine
Short half life
[< 3 hrs]
Second Generation
Nicardipine
Felodipine
Isradipine
Long half life
[< 14 hrs]
Third Generation
Amlodipine
Very long
[> 30 hrs]
192 Adya Jain et al
Zeolites are nanoporous crystalline aluminosilicates containing labyrinth of molecular
dimensions which can be filled by water or other guest molecules. Zeolites are
obtained as natural minerals which can also be artificially engineered. Major
applications of Zeolite are adsorption, catalysis and ion-exchange property. Zeolite
exclusive advantages includes less or noncorrosive nature, no waste or disposal
problem, abundance, low cost, high thermostability, great adaptability to practically
all types of catalysis, heterogeneous i.e. easily separable from reaction mixture, great
acid strength, easier scale up for continuous processes, etc. Hence, we decided to
work on zeolite as catalyst for the synthesis of 1,4-Dihyropyridine drug molecules.
The use of catalyst greatly enhances the yield percentage and purity of drug molecules
therefore fulfills the needs of huge demands for pharmaceutical medicines.
Zeolite Beta is one of the large pore and high synthetic silicate zeolite thus attribute
higher catalytic activity, higher hydrophobicity, high cation concentration and acidic
strength. Therefore we had chosen this zeolite as catalyst due to its remarkable
properties. Zeolite Beta consists of an intergrowth of two distinct structures termed
Polymorphs A and B (hybrid of tetragonal and monoclinic structure). [22] The
polymorphs grow as two-dimensional sheets and the sheets randomly alternate
between the two. Both polymorphs have a three dimensional network of 12-ring
pores. Material formula of zeolite β is Na0.92 K0.62 (TEA)7.6 [Al4.53Si59.47O128] with
Si/Al ratio of 13.1.
The BEA framework topology attracts much attention because of the large available
micropore volume, large-pore channel system and the presence of active sites in
different concentrations that are useful in a number of acid-catalyzed reactions e.g.,
dewaxing, hydroisomerization, hydrocracking, alkane and aromatic alkylation,
disproportionation and other organic synthesis processes [23,24]. Therefore we had
chosen this zeolite for the synthesis of pharmaceutical drug molecules because of
unique exceptional properties.ad chosen this zeolite
To best of our knowledge, these novel drug intermediates are first time synthesized by
using Cr2O3-H-β zeolite as nanoporous catalyst.
Fig 4: Polymorph combination for the formation of Zeolite Beta
A Hantzsch condensation reaction / Dihydropyridine Cascade Synthesis on Zeolite substrate 193
2. EXPERIMENTAL
2.1 Synthesis of Zeolite and its derivatives
2.1.1. Synthesis of Zeolite Beta
In a 250 ml round bottomed flask, 29.7 ml distilled water, 44.8 ml Tetramethyl
ammonium hydroxide (template), 0.265 g NaCl, 0.72 g KCl and 14.77 g silica gel was
added to it. Then 10 ml distilled water, 0.165 g NaOH and 0.895 g sodium aluminate
solution was mixed to the above solution (Scheme 1). This mixture was stirred for 10
min and a thick gel was obtained. This thick gel was kept in autoclave at 135ºC for 18
h. Thereafter obtained mixture was centrifuged, washed and filtered by double
distilled water (pH=12). Finally precipitate was dried in oven for an overnight at
77ºC.
2.1.2 Conversion of Na-form zeolites to H-form zeolites
In a 250 ml round bottomed flask, 9 g of zeolite (Na form), 7.230 g NH4Cl and 13.80
ml distilled water mixed with 0.1M HCl solution to reach pH=4. This reaction
mixture was stirred for 30 min at 60ºC. Thereafter obtained material was washed and
filtered by double distilled water. Finally precipitate was dried in oven at 60ºC for 24
h. Further the powdered mixture was calcinated at 200ºC for 60 min (Scheme 2).
2.1.3 Synthesis of Cr2O3-zeolites beta
In a 250 ml round bottomed flask, 1.5 g zeolite and 20 ml of 1M Anhydrous Sr(NO3)2
were mixed and stirred for 5 h. During stirring 50 ml of 0.2 M KMnO4 solution was
added suddenly. Thereafter the reaction mixture was washed with double distilled
water and dried in oven at 100ºC for more than overnight. Finally the powdered form
was calcinated at 550ºC for 4h (Scheme 3).
Scheme 1, 2 and 3: Synthesis and Modification of Zeolite
194 Adya Jain et al
2.2 Synthesis of 1,8-Acridinedione derivatives (3,3,6,6-Tetramethyl-3,4,6,7,9,10-
hexahydro-1,8-acridinedione)
In ethanol (solvent), Primary amine (1 mmol) was added to the mixture of 5, 5-
dimethyl-1,3-cyclohexanedione (dimedone) (2 mmol), an aromatic aldehyde (1 mmol)
and zeolite (0.1 g) at 90 °C (Fig. 5). Reaction completion was realized by Thin Layer
Chromatography. The reaction mixture was filtered and the product was obtained as
filtrate, collected and dried at room temperature. The purification of solid residue was
performed by recrystallizing from ethanol to obtain pure 1, 8-dioxo-
decahydroacridine derivative form. The synthesized compound was characterized by
the help of FTIR, LC-MS and 1H-NMR.
𝐏𝐫𝐨𝐝𝐮𝐜𝐭 𝐲𝐢𝐞𝐥𝐝 (%) =𝐀𝐜𝐭𝐮𝐚𝐥 𝐲𝐢𝐞𝐥𝐝 (𝐠)
𝐓𝐡𝐞𝐨𝐫𝐢𝐭𝐢𝐜𝐚𝐥 𝐲𝐢𝐞𝐥𝐝 (𝐠)× 𝟏𝟎𝟎%
O
O
CH3
CH3
+ RCHO NH2R1
+Refluxing Water
90 °C, 15-20min.N
O O
CH3CH3
CH3
CH3
R1
R
Fig 5: One Pot Hantzsch Condensation Reaction
Table 1: Synthesis of Different derivatives of 1, 8-Acridinedione:
S.No. Benzaldehyde (R) Amine (R’) Product Yield (%)
1. O
Cl
NH2
Cl
Cl
N
O O
CH3CH3
CH3
CH3
Cl
Cl
Cl
86.29
2. O
OH
NH2
Cl N
O O
CH3CH3
CH3
CH3
Cl
OH
90.23
A Hantzsch condensation reaction / Dihydropyridine Cascade Synthesis on Zeolite substrate 195
3. O
OH
NH2
Cl
Cl
N
O O
CH3CH3
CH3
CH3
Cl
OH
Cl
89.88
4. O
N+
O-
O
NH2
N
O O
CH3CH3
CH3
CH3
N+ O
-O
88.49
5. O
Cl
NH2
Cl N
O O
CH3CH3
CH3
CH3
Cl
Cl
84.82
O
O
CH3
CH3
ArCHO
aldol
O
O
CH3
CH3
Ar
O
O
Michael
O O
O O
Ar
NH2
O
O O
N
NHO
O O
O O
N
OH
Ar
Ar
Ar
-H2O
O O
N
Ar
Scheme 2: Plausible mechanism for the formation of 1, 8-Acridinedione
196 Adya Jain et al
3.1 Result and Discussion [I]
Melting points were determined in open capillaries from melting point instrument.
Infrared spectra of the synthesized drug intermediates and zeolites were recorded by
“Spectrumto-Perkin Elmer” spectrophotometer in the range of 4000–400 cm-1 by
using KBr pellets. X-Ray diffraction spectra were recorded by using “Miniflex 600”
Diffractometer. 1H-NMR spectra were determined in DMSO-d6 solvent by the help
of JEOL-JNM-ECA Series (Delta V4.3)-400 MHz-FT-NMR. Data for 1H NMR are
reported as follows: chemical shift, integration, multiplicity (s = singlet, d = doublet, t
= triplet, q = quartet, m = multiplet) and coupling constants. BET surface area and
porosity of zeolite samples was determines by using Gemini VII 2390 Surface Area
Analyzer (Micromeritics). Analytical thin layer chromatography was performed using
0.25 mm silica gel plates (Ethyl Acetate: n-Hexane :: 3:1).
3.1.1 Fourier Transform Infrared Spectroscopy
The finger print region of FT-IR determines the formation of zeolite. The absorption
peaks between 750-700 cm-1 (i.e. 743.42, 734.91, 726.83, 712.83 and 702.84)
corresponds to the symmetric stretching vibration of SiO4 groups. The bands around
635.57, 546.81 and 467 cm-1 relates to bending vibration of SiO4 groups or in the
vibration modes of the 4-membered rings of silicate chains. The stretching vibration
of SiO4 are shifted towards lower frequency indicating that the presence of the
internal Si-O···HO-Si bonds.
Fig 6: FT-IR of H-beta and Cr2O3-beta
3.1.2 Scanning Electron Microscope
The SEM micrograph of zeolite shows the interconnection of porous structure by
agglomerating of nanoparticles of Cr2O3 on H-beta with an average particle size less
than 50 μm.
4000 3500 3000 2500 2000 1500 1000 500
0
5
10
15
20
25
% T
rans
mitt
ance
Wavelength (cm-1)
H-Beta
Cr20
3-H-Beta
A Hantzsch condensation reaction / Dihydropyridine Cascade Synthesis on Zeolite substrate 197
Fig 7: SEM micrograph of Zeolite Cr2O3-H- β
3.1.3 X-Ray Diffraction
The X-Ray Diffraction pattern is the fingerprint of the crystalline phase of zeolite.
From the diffraction signals, the sharp peaks at 2θ value corresponding to 25.0 for
zeolite-H-β and Cr2O3- H-β are clearly observed. Generally sharp peaks determine the
crystalline nature of material, but here the broadening of peaks determines the
polycrystalline nature of zeolite beta. It is also clearly observed that the X-ray
diffraction patterns of H-forms and metal oxide exchanged forms of zeolites are
similar to the diffraction patterns of their respective parent zeolites. These
observations indicate that zeolite framework has not undergone any significant
structural change during the incorporation of metal ion and crystallinity of the zeolite
was preserved.
Fig 8 and 9: XRD of H-beta and H-beta- Cr2O3 respectively
3.1.4 BET Analysis
The BET surface area of H-BETA zeolite was found to be 310.1525 m²/g, Langmuir
surface area: 446.6285 m²/g, BJH adsorption cumulative surface area of pores
2-theta (deg)
Inte
nsity (
cou
nts
)
20 40 60 80
0
1000
2000
3000
4000
2-theta (deg)
Inte
nsity (
cou
nts
)
20 40 60 80
0
1000
2000
3000
4000
198 Adya Jain et al
between 17.000 A0 and 3000.000 A0 widths: 348.805 m²/g, BJH desorption
cumulative surface area of pores between 17.000 A0 and 3000.000 A0 widths:
408.7747 m²/g.
The BET surface area of Cr2O3-H-BETA zeolite was found to be 139.4775 m²/g,
Langmuir surface area: 202.3463 m²/g, BJH adsorption cumulative surface area of
pores between 17.000 A0 and 3000.000 A0 widths: 166.174 m²/g, BJH desorption
cumulative surface area of pores between 17.000 A0 and 3000.000 A0 widths:
199.1166 m²/g.
Fig 10 and 11: BET analysis representing Relative Pressure v/s Quantity Adsorbed
and Pore width v/s Pore volume
3.2 Result and Discussion [II]
Table 2, Graph 1: Studying the yield of 9-(4-OH C6H5)-10-(3, 4-Cl2 C6H5)-3, 3, 6, 6-
Tetramethyl acridine-1, 8-dione [6] from different zeolites derivatives
S.No. Solvent Catalyst Yield (%)
1. Ethanol H-β 89.88
2. Ethanol Cr2O3-β 85.45
All reactions were carried out at 90ºC from 30-40 min. with catalyst amount of 0.10 g.
0.0 0.2 0.4 0.6 0.8 1.0
0
50
100
150
200
250
300
350
400
450
500
550
600
Qu
an
tity
Ad
so
rbe
d (
cm
³/g
ST
P)
Relative Pressure (P/Po)
Cr2O
3-H-Beta
H-Beta
0 200 400 600 800 1000
0.0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
1.1
1.2
dV
/dlo
g(w
) P
ore
Vo
lum
e (
cm
³/g
·Å)
Pore Width (Å)
Cr2O
3-H-Beta
H-Beta
89.8885.45
80
85
90
95
H-β Cr2O3-β
Yie
ld (
%)
Zeolite
Different Catalyst
A Hantzsch condensation reaction / Dihydropyridine Cascade Synthesis on Zeolite substrate 199
Table 3, Graph 2: Studying the yield of 9-(4-OH C6H5)-10-(3, 4-Cl2 C6H5)-3, 3, 6, 6-
Tetramethyl acridine-1, 8-dione [6] from different solvents
S.No. Solvent Yield (%)
1. Ethanol 89.88
2. Acetonitrile 86.60
3. Chloroform 81.23
4. 1,4-Dioxane 76.91
5. Toluene 75.35
All reactions were carried out at 90ºC from 30-40 min. with catalyst H-β amount of 0.10 g .
Table 4, Graph 3: Studying the yield of 9-(4-OH C6H5)-10-(3, 4-Cl2 C6H5)-3, 3, 6, 6-
Tetramethyl acridine-1, 8-dione [6] at different temperature
S.No Temperature Yield (%)
1. 0ºC 31.90
2. 30ºC 53.31
3. 60ºC 64.77
4. 90ºC 89.88
5. 120ºC 47.29
Table 4, Graph 3: Studying the yield of 9-(4-OH C6H5)-10-(3, 4-Cl2 C6H5)-3, 3, 6, 6-
Tetramethyl acridine-1, 8-dione [6] at different time
S.No. Time Yield (%)
1. 15 min 34.16
2. 30 min 52.09
3. 45 min 67.41
4. 60 min 89.88
5. 75 min 80.23
89.8886.6
81.2376.91 75.35
65707580859095
Yie
ld (
%)
Solvents
31.9
53.3164.77
89.88
47.29
0
20
40
60
80
100
0ºC 30ºC 60ºC 90ºC 120ºC
Yie
ld(%
)
Temperature
34.16
52.09
67.41
89.8880.23
0
20
40
60
80
100
15 min 30 min 45 min 60 min 75 min
Yie
ld (
%)
Time
200 Adya Jain et al
Spectroscopic data of some synthesized drugs
9-(4-OH C6H4)-10-(4-Cl C6H4)-3, 3, 6, 6-tetramethyl acridine-1, 8-dione: FT-
IR (KBr in cm-1) 3883.47, 3055.4, 2999.5, 2850.78, 1718.37, 1488.5, 1517.61,
755.12, 724.33; UV-Vis. λ max – 893.2 nm Absorbance at 0.100 Å; m/z = 476.5
(M+H) +.1H NMR (400 MHz, DMSO-d6): d = 0.74 (s, 6 H, 2 CH3), 0.87 (s, 6 H, 2
CH3), 1.75 (d, J = 17.6 Hz, 2 H, 2 CH), 2.03 (d, J = 16.0 Hz, 2 H, 2 CH), 2.18 (d, J =
16.0 Hz, 2 H, 2 CH), 2.18 (d, J = 17.6 Hz, 2 H, 2 CH), 5.00 (s, 1 H, CH), 7.30 –7.49
(m, 6 H, ArH), 7.68 (d, J = 8.8 Hz, 2 H, ArH), 9.05 (s, 1H, -OH ).
9-(4-OH C6H4)-10-(3, 4-Cl2 C6H3)-3, 3, 6, 6-tetramethyl acridine-1, 8-
dione: FT-IR (KBr in cm-1) 3471.47, 3184.5, 2949, 2719.14, 1674.64, 1575, 1460,
1575, 825.5 and 753.56; UV-Vis. λ max – 893.5 nm Absorbance at 0.142 Å; m/z = 511
(M+H) +.1H- NMR (400 MHz, DMSO-d6): d = 0.72 (s, 6 H, 2 CH3), 0.89 (s, 6 H, 2
CH3), 1.78 (d, J = 17.6 Hz, 2 H, 2 CH), 2.01 (d, J = 16.0 Hz, 2 H, 2 CH), 2.19 (d, J =
16.0 Hz, 2 H, 2 CH), 2.20 (d, J = 17.6 Hz, 2 H, 2 CH), 5.01 (s, 1 H, CH), 7.30 –7.49
(m, 6 H, ArH), 7.68 (d, J = 8.8 Hz, 2 H, ArH), 9.05 (s, 1H, - OH ).
9, 10-Bis (4-ClC6H4)-3, 3, 6, 6-tetramethyl acridine-1, 8-dione: FT-IR (KBr
in cm-1) 3051.84, 2960.17, 2873.28, 1688, 1575.18, 1424.78, 852.7, 762.46; UV-Vis.
λ max – 893.5 nm; Absorbance at 0.142 Å; 1H NMR (400 MHz, DMSO-d6): d = 0.72
(s, 6 H, 2 CH3), 0.89 (s, 6 H, 2 CH3), 1.89-2.01 (d, J = 16.0 Hz, 2 H, 2 CH2), 2.42 (d, J
= 17.6 Hz, 2 H, CH2), 5.01 (s, 1 H, CH), 7.30 –7.49 (m, 6 H, ArH), 7.68 (d, J = 8.8
Hz, 2 H, ArH).Anal. Calcd for C29H29Cl2NO2: C, 70.44; H, 5.91; N, 2.83. Found: C,
70.28; H, 6.05; N, 2.90.; m/z = 470 (M+H)+ .
Fig. 12: FT-IR of 9, 10-Bis (4-ClC6H4)-3, 3, 6, 6-tetramethyl acridine-1, 8-dione
4000 3500 3000 2500 2000 1500 1000 500
-5
0
5
10
15
20
25
30
35
40
(%)
Tra
nsm
itta
nce
Wavenumber(cm-1)
9,10-bis-(4-Cl C6H
5) Acridine-1,8-dione
A Hantzsch condensation reaction / Dihydropyridine Cascade Synthesis on Zeolite substrate 201
Fig 13: 1H-NMR of 9, 10-Bis (4-ClC6H4)-3, 3, 6, 6-tetramethyl acridine-1, 8-dione
Fig 14: LC-MS of 9, 10-Bis (4-ClC6H4)-3, 3, 6, 6-tetramethyl acridine-1, 8-dione
9-(4-OH C6H4)-3, 3, 6, 6-tetramethyl acridine-1, 8-dione: FT-IR (KBr in
cm-1) 3286.91, 3056.78, 2914.20, 2872.61, 1666.86, 1512.53, 1593.36, 832.62,
805.15; UV-Vis. λ max – 893.5 nm Absorbance at 0.142 Å; m/z = 365 (M+H) +. 1H-
NMR (400 MHz, DMSO-d6): d = 0.75 (s, 6 H, 2 CH3), 0.88 (s, 6 H, 2 CH3), 1.75-1.99
(d, J = 17.6 Hz, 2 H, 2 CH2), 2.14-2.21 (d, J = 16.0 Hz, 2 H, 2 CH2), 4.85 (s, 1 H,
CH), 6.61(m, 2H, ArH), 7.02 (m, 2 H, ArH), 9.02 (s, 1H, NH), 9.25 (s, 1H, OH).
469.5 470.0 470.5 471.0 471.5 472.0 472.5 473.0 m/z
2.0
3.0
4.0
5.0
6.0
7.0
8.0
Inten.(x100)
470.50
202 Adya Jain et al
Fig 15: FT-IR of 9-(4-OH C6H4)-3, 3, 6, 6-tetramethyl acridine-1, 8-dione
Fig 16: 1H-NMR of 9, 10-Bis (4-ClC6H4)-3, 3, 6, 6-tetramethyl acridine-1, 8-dione
4000 3500 3000 2500 2000 1500 1000 500
10
20
30
40
50
60
70
% T
rans
mitt
ance
Wavelength (cm-1)
9(4-OH C6H
6)Acridinedione
A Hantzsch condensation reaction / Dihydropyridine Cascade Synthesis on Zeolite substrate 203
Fig 17: LC-MS of 9, 10-Bis (4-ClC6H4)-3, 3, 6, 6-tetramethyl acridine-1, 8-dione
4. CONCLUSION
The foremost merits of this work are significant due to its competency,
environmentally benevolent methodology, recyclable as well as thermally stable
zeolite heterogeneous catalytic applicability. In this study we found that, with
escalating electronegativity, ionization energy decreases consequently reactivity
increases since it uses less energy to lose electrons. The reactivity order H (2.1) > Cr
(1.6) has been confirmed experimentally. The reactivity was found highest in ethanol
with H-β at 90ºC for 60 min. i.e. 89.88%. Further the yield of different derivative is
affected by the presence of electron withdrawing groups (EWG) and electron
donating groups (EDG). Yield of acridine drugs having EWG was found higher than
those for having EDG.
5. ACKNOWLEDGEMENT
I owe to my mentor for supporting and guiding me to make this work possible and
Central Instrumentation Laboratory (CIF), Jiwaji University, Gwalior, M.P. for
providing necessary instrument support (FT-IR, XRD, LC-MS). I am also thankful to
DRDE, Gwalior for providing BET surface area studies and IIT Delhi for 1H-NMR
studies.
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Yano, Inorg. Chim. Acta, 1998, 279, 51–57.
[3] K. Venkatesan, S. S. Pujari and K. V. Srinivasan, Synth. Commun., 2008, 39,
228–241.
[4] R. Ulus, I˙. Yesildag˘, M. Tanc, M. Bu¨lbu¨l, M. Kaya and C. T. Supuran,
Bioorg. Med. Chem., 2013, 21, 5799–5805.
100 200 300 400 500 600 700 800 900 m/z0.0
2.5
5.0
7.5Inten.(x100,000)
364.10
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