Discussion Addendum for: Convenient Preparation of 3 …orgsyn.org/Content/pdfs/procedures/v96p0098.pdf · 2019-04-12 · Org. Synth. 2019, 96, 98-109 99 DOI: 10.15227/orgsyn.096.0098

Org. Synth. 2019, 96, 98-109 Published on the Web 4/18/2019 DOI: 10.15227/orgsyn.096.0098 Ó 2019 Organic Syntheses, Inc.

98

DiscussionAddendumfor:ConvenientPreparationof3-EthoxycarbonylBenzofuransfromSalicylaldehydesandEthylDiazoacetate Mizzanoor Rahaman1 and M. Mahmun Hossain*1 Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, 3210 North Cramer Street, Milwaukee, Wisconsin 53211-3029, United States Original Article: Dudley, M. E.; Morshed, M. M.; Hossain, M. M. Org. Synth. 2009, 86, 172–180.

The benzofuran scaffold is an important heterocyclic core component found in several natural products and in polymers.2,3 Typically, 2,3-disubstituted benzofurans are notable building blocks in many medicinal and biologically active compounds.4-9 In addition, 3-substituted benzofurans act as anticancer agents,10 antitubercular agents,11 antimicrobial agents,12

antiviral agents,13 and anti-inflammatory agents.14 They also act as enzyme inhibitors,15,16 ischemic cell death inhibitors,17 receptor agonist-antagonists,18

and use as diagnostic imaging agents targeting amyloid plaques in Alzheimer's disease.19 Although syntheses of 2-substituted or 2,3-disubstituted benzofurans are most common, the syntheses of 3-substituted benzofurans are rare.20-24 In 2004, our group reported an unprecedented reaction of acrylate formation from readily available aldehydes starting materials and ethyl diazoacetate (EDA) in the presence of Brønsted acid, HBF4· OEt2.25 While studying the substrate scope of benzaldehydes to prepare substituted 3-hydroxyacrylates, our group reacted salicylaldehyde with EDA and isolated a very low mass of acrylates with a larger portion of

CHO

OH O

COOEt1. N2CHCOOEt, HBF4, (10 mol%), CH2Cl2, rt

2. H2SO4, rt

ClCl

Org. Synth. 2019, 96, 98-109 DOI: 10.15227/orgsyn.096.0098 99

the hemiacetal, 3-ethoxycarbonyl-2-hydroxy-2,3-dihydrofuran. The hemiacetal underwent dehydration in the presence of concentrated H2SO4 to form the 3-ethoxycarbonyl benzofuran. The general scope of the reaction was also investigated using various commercially available substituted salicylaldehydes and EDA. The acid catalyzed dehydration via cyclization produced the products in excellent yields.26 Alternatemethodstoprepare3-alkoxycarbonylbenzofurans

Most alternate syntheses of 3-alkoxycarbonyl benzofuran involve

transition metal catalysis. In 1982, Ortar et al. reported the synthesis of 3-methoxycarbonyl benzofurans by the oxidation reaction of chromanones with excess thallium trinitrate (TTN) in methanol in the presence of trimethyl orthoformate (TMOF). The product was isolated as a pale-yellow liquid in only 23% yield (Scheme 1).27

O

O

TTN, TMOF

MeOH, 6 h O

OMeO

R R

Scheme 1. Synthesis by a thallium catalyzed oxidation annulation

Henke and coworkers reported a new synthetic route to 3-ethoxycarbonyl benzofuran (Scheme 2a).28 In this two-step procedure, the first step involved the Michael addition of 2-bromophenol with ethyl propionate in the presence of trimethylamine to prepare 3-(2-bromophenoxy)-acrylic acid ethyl ester. Second, a palladium-catalyzed intramolecular Heck coupling of the 3-(2-bromophenoxy)acrylic acid ester created 3-ethoxycarbonyl benzofuran as a yellow oil in 61% yield.

Later, Frontier et al. applied a similar synthetic strategy as reported by Henke et al.28 involving 3-(2-iodophenoxy)acrylic acid ethyl ester to prepare 3-ethoxycarbonyl benzofuran in 74% yield (Scheme 2b).29 The ester was produced from the reaction of 2-iodophenol and ethyl propionate in the presence of N-methylmorpholine (NMM).

Wang and coworkers reported the formation of 3-ethoxycarbonyl benzofuran in 81% yield from (E)-3-phenoxyacrylates through the direct oxidative cyclization by a palladium catalyst (Scheme 2c).30 The


corresponding acrylates were prepared from phenol and propynoic acid ethyl ester in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO).

Scheme 2. Syntheses by a palladium-catalyzed cyclization

Morice et al. reported the preparation of several 3-methoxycarbonyl benzofurans based on the conversion of 3-coumaranones into their corresponding triflates, followed by palladium assisted CO insertion reactions in methanol (Scheme 3).31 3-Coumaranones were prepared from o-methoxybenzoic acids with oxalyl chloride and diazomethane followed by decomposition of the diazo ketone in acetic acid/sodium acetate solution.

Scheme 3. Synthesis by a palladium assisted CO insertion

Karchava et al. reported the preparation of 3-methoxycarbonyl benzofuran from hydroxyacrylates. First, the methyl-2-bromophenylacetates

Br

OH Et3N, THF, rt

Br

O

O

OEt

O

OOEt

Pd(OAC)2, PPh3

NaHCO3, DMF, 110 °CR R R

I

OH NMM, THF, rt

I

O

O

OEt

O

OOEt

Pd(OAC)2, PPh3

Et3N, CH3CN, 80 °CR R R

OH O

O

OEt

O

OOEt

Pd(OAC)2, PPh3

CF3CO2Ag, C6H6, 110 °CDABCO, CH2Cl2RRR

a.

b.

c.

O

O

O

O

O

O

O

O

O

OOMe

DIPEA, Tf2O

CH2Cl2, rt, 16 h

OMe

O

OHNaOAc, HOAc

OMe

O

O

OTfPd(OAc)2, dppp, NEt3, MeOH

CO (1 atm), DMF, 80 °C, 2 h

1. (COCl)2

2. CH2N2, Et2O

N2

R R R

R R


were treated with methyl formate in the presence of sodium hydride and after acidic work up, the mixture provided the acrylate product. Later, a copper-catalyzed cyclization of the acrylate produced 3-methoxycarbonyl benzofuran in 88% yield (Scheme 4).32

Br

1. NaH, HCOOMe, 1 h

2. 10% HCl, NaHCO3 Br

OMeO

CuI, K2CO3, DMF

100 °C, 2 h O

OMeO

OMe

OOH

R R R

Scheme 4. Synthesis by a copper-catalyzed cyclization

Recently, in 2016, Yao et al. reported the synthesis of 3-ethoxycarbonyl benzofuran by a Rh(III)-catalyzed reaction between salicylaldehyde and ethyl 2-diazo-3-oxopropanoate in dichloroethane (DCE).33 Silver triflimide (AgNTf2) favored the formation of 3-ethoxycarbonyl benzofuran via a tandem C-H activation/decarbonylation/annulation process in 72% yield (Scheme 5).

OH O

OOEt

[RhCp*(Cl)2]2, PPh3

AgNTf2, DCE, 50 °CH

O

N2

O

OEtR

R

H

O

- CO

Scheme 5. Synthesis by a rhodium-catalyzed annulation Applicationsofourmethodinorganicsynthesis

Compared to the alternative syntheses of 3-alkoxycarbonyl benzofuran, our synthetic method is simple, less time consuming, and high yielding with inexpensive and commercially available starting materials. This one-pot synthetic method has been used by us and by other groups in the preparation of several biologically active compounds as described herein.

Telvekar and coworkers synthesized N’-benzylidene benzofuran-3-carbohydrazides from 3-ethoxycarbonyl benzofurans (Scheme 6).34 All these compounds were found to be active against tuberculosis and showed antifungal activity against Candida albicans.


Scheme 6. Synthesis of N’-benzylidene benzofuran-3-carbohydrazide

Eccles and coworkers synthesized several leukotriene A4 hydrolase (LTA4H) inhibitors from 3-ethoxycarbonyl benzofuran (Scheme 7).35 LTA4H inhibitors are used in inflammatory diseases, such as bowel disease, rheumatoid arthritis, chronic obstructive pulmonary disease, and asthma.

Scheme 7. Synthesis of leukotriene A4 hydrolase (LTA4H) inhibitor

Morrow et al. synthesized pterocarpene and coumestan-type

heterocycles by the Mitsunobu coupling of 3-(hydroxymethyl)benzofurans with o-iodophenols (Scheme 8).36 Pterocarpans have been shown to exhibit broad spectrum activity against gram-positive bacteria and vancomycin-resistant strains of enterococci. Coumestans, such as coumestrol and flemmichapparin C, have also been shown to display antibacterial, antifungal, and antimyotoxic effects.

1. N2CHCOOEt, HBF4•OEt2, CH2Cl2, rt

2. H2SO4, rtOH

R1

O

R1

O

HOEt

O

O

R1

HN

O

R1 = H, R2 = HR1 = Cl, R2 = ClR = Ar

R2R2

H2N NH2 . H2O

C2H5OH, reflux5-7 h

O

R1

HN

O

R2

NH2 O Ar

C2H5OH, reflux5-7 h

NAr

R2

OH

1. N2CHCOOEt, HBF4•O(Me)2, CH2Cl2

2. toluene, reflux O

O

H

OMeO

BBr3, CH2Cl2

-78 °CMeO MeO O

OMeO

HO

S

NCl

Cs2CO3CH3CN, 50 °C O

OMeO

O

N

S

DIBALH or LAH

CH2Cl2, 0 °CO

OH

O

N

S

HNR1R2

K2CO3, DMFO

NR1R2

O

N

S

NR1R2 = Piperidine, morpholine, isonepicotic acid, N-(piperidin-4-yl)acetamide, 1-(piperidin-4-yl)pyrrolidin-2-one, 1-(2,5-diazabicyclo[2.2.1]heptan-2-yl)ethanone


OH

1. N2CHCOOEt, HBF4CH2Cl2, rt

2. H2SO4, rt O

O

HOEt

O

O

OH

DIAD, Ph3P, THF

DIBAL-H

CH2Cl2

HO

I

O

O

IO

Pd(OAc)2, KOAc

Bu4NBr, DMF

O

O

O

PCCCH2Cl2

OR1 R1 R1

R2

R1 R1R2

R2 R2

R1Pterocarpenes Coumestans

Scheme 8. Synthesis of pterocarpenes and coumestans

Tolstikov et al. reported several regioselective Diels–Alder reactions of Danishefsky’s diene with 3-ethoxycarbonyl benzofurans (Scheme 9).37 These reactions provided effective method for the construction of the heterocyclic skeleton of hexahydrodibenzofuran-7-one and tetrahydrodibenzofuran-7-one. These tricyclic fragments are the structural motifs of many pharmacologically vital substances, such as plant alkaloids morphine, galanthamine, lycoramine, and lunarine, linderol A, and several selective estrogen receptor b -agonists.

Scheme 9. Construction of heterocyclic skeleton

Elofsson and coworkers constructed a library based on the 3-carboxy 2-aryl benzofuran scaffold from 3-ethoxycarbonyl benzofuran (Scheme 10).38 These two scaffolds are core components in many biologically active natural and synthetic compounds of which many display a wide range of activities including antiviral, antibacterial, anti-inflammatory, antiangiogenic, and antimitotic activities.

OH

1. N2CHCOOEt, HBF4•OEt2, CH2Cl2

2. H2SO4, rt O

O

H

OEtO

PhMe, 170 °C, 48-52 hor, PhMe, microwave

O

MeO OSiMe3

CH2

O

EtO OMe

H

1. H4NF, MeOH, -15 °C2. TsOH, MeOH, rt3. CF3COOH, CH2Cl2, rt4. TsOH, PhMe, 110 °C O

O

EtO OMe

H O

O

EtO OMe

H O

O

EtO

H

O O O

OSiMe3

R R R

R RR


Scheme 10. Synthesis of 2-arylbenzofuran-3-carboxamide derivatives

Zhao et al. reported a total synthesis of paeoveitol, the norditerpene natural product which has antidepressant ability, from 3-ethoxycarbonyl benzofuran (Scheme 11).39 Our published procedure was employed to synthesize 3-ethoxycarbonyl benzofuran, which was reduced to paeoveitol D. Paeoveitol was synthesized by an unusual intermolecular ortho-quinone methide cycloaddition with paeoveitol D with excellent regio- and diastereoselectivity.

Scheme 11. Total synthesis of paeoveitol via paeoveitol D

Later, Chen and coworkers reported the first catalytic asymmetric total synthesis of (+)-paeoveitol and (-)-paeoveitol from 3-ethoxycarbonyl

1. N2CHCOOEt, HBF4•OEt2, CH2Cl2, rt

2. H2SO4, rtOH O

O

HOEt

O

R1R1 O

OEtO

R1

B(OH)2

O

OEtO

R1

O

NO

R1

Ar

R3

R4

O

OHO

R1

O

OEtO

R1

I

B(OCH3)3, LDA

THF, -78 °C

Ar

Ar

I2, LDA, THF

-78 °C, rt

boronic acidPdCl2(dppf).DCM

Na2CO3, DME/H2O

iodo derivativesPdCl2(dppf).DCMNa2CO3, DME/H2O

amine TBTU, DMF

NaOH

THF/H2O

OH

1. N2CHCOOEt, HBF4•OEt2CH2Cl2, rt

2. H2SO4, rt O

O

H

OEtO

O

OH

ZnCl2, CH2Cl2

DIBAL-H

CH2Cl2

O

O

HO

Me

HO

Me

HO

Me

HO Me

OH HO

Me H

OH

Me

Me

OHHO

Me

PaeoveitolPaeoveitol D


benzofuran via a biomimetic hetero-Diels-Alder reaction in the presence of chiral phosphoric acids as catalysts (Scheme 12).40

Scheme 12. Asymmetric synthesis of (+)-paeoveitol and (-)-paeoveitol

Bongen et al. reported an efficient asymmetric synthesis of 7-benzoyl-2,3-

dihydro-1-benzofuran-3-carboxylic acid, BRL-37959 (Scheme 13).41 3-Ethoxycarbonyl benzofuran was reduced by magnesium turnings in methanol to form 2,3-dihydrobenzofuran-3-carboxylic acid ethyl ester, which was resolved by dynamic kinetic resolution. Friedel-Crafts acylation reaction of the enantiopure product followed by acidic hydrolysis produced (R)-BRL-37959, which acts as analgesic agents with low gas irritancy.5

Scheme 13. Synthesis of enantiopure (R)-BRL-37959

Recently, in 2018, our group reported the synthesis of 7-benzoyl-2,3-dihydro-1-benzofuran-3-carboxylic acid, BRL-37959 and its analogs from 3-ethoxycarbonyl benzofuran (Scheme 14).42 To synthesize BRL-37959,

OH

1. N2CHCOOEt, HBF4•Et2OCH2Cl2, rt

2. H2SO4, rt O

O

H

OEtO

O

OH

chiral phosphoric acid cat.

CH2Cl2, rt

DIBAL-H

CH2Cl2

O

O

MeO

Me

MeO

Me

HO

Me

HO Me

OH HO

Me H

OH

Me

Me

OHHO

Me

(+)-Paeoveitol

BBr3

CH2Cl2 O

OEtHO

Me

O

O

OHO

Me H

OH

Me

Me

OH

(-)-Paeoveitol

, or

Paeoveitol D

OH

1. N2CHCOOEt, HBF4•Et2O, CH2Cl2

2. H2SO4, rt

O

HCAL-B, 36 °C

KPi buffer

(100 mm, pH 8.5)

O

OEtO

O

OEtO

O

OEtO

1. Mg/MeOH

2. EtOH, H2SO4

CS2, AlCl340 °C, 72 h

Cl Cl

Cl H2O, H2SO4

rtO

Cl

OEt

O

O

O

Cl

OH

O

O

Cl

O

Cl


incorporation of a benzoyl group at the C-6 position of benzofuran ring by the Friedel-Crafts acylation reaction was the main challenge. Our recent method demonstrates that bismuth (III) trifluoromethanesulfonate can be used as a catalyst for the Friedel-Crafts acylation reaction with good yield. This efficient method allowed the production of many analogs of BRL-37959 in high yield.

Scheme 14. Synthesis of BRL-37959 and its analogs

In summary, 3-ethoxycarbonyl benzofuran plays a pivotal role in the field of medicinal and pharmaceutical chemistry. The concise synthesis of 3-ethoxycarbonyl benzofuran was reported by our group with excellent yield from commercially available starting materials. In this addendum, we discussed several alternate methods for the preparation of 3-ethoxycarbonyl benzofuran and applications of our published method to synthesize important biologically active compounds. In the future, our developed method of preparing 3-ethoxycarbonyl benzofuran could be a valuable procedure in making benzofuran-ring containing natural and unnatural products. References 1. Department of Chemistry and Biochemistry, University of Wisconsin-

Milwaukee, 3210 North Cramer Street, Milwaukee, Wisconsin 53211-3029, United States. Email: [email protected]

2. Yeung, K.-S. Heterocycl. Chem. 2012, 29, 47−76.

OH

R11. N2CHCOOEt,

HBF4•Et2O, CH2Cl2, rt

2. H2SO4, rt O

R1O

H

OEtO

Mg, I2

MeOH, 72 h O

R1OMe

O

Cl

OR2

Bi(OTf)3nitrobenzene, 90 °C

O

R1

OMe

ONaOH

MeOH, 12 h

O

R2

O

R1

OH

O

O

R2


3. Nevagi, R. J.; Dighe, S. N.; Dighe, S. N. Eur. J. Med. Chem. 2015, 97, 561−581.

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M. Mahmun Hossain received his MSc degree in chemistry from the University of Dhaka, Bangladesh. In 1985, he received his PhD from the University of South Carolina. After about three years of postdoctoral study with Professor Jack Halpern at the University of Chicago, he joined the Department of Chemistry & Biochemistry at the University of Wisconsin-Milwaukee as an Assistant Professor. Later, he was promoted to Professor, and received a research award from the UWM Foundation for his outstanding research and creativity.

Mizzanoor Rahaman received his BS and MS degree in Chemistry from the University of Dhaka, Bangladesh. He began PhD studies in Organic Chemistry at the University of Wisconsin-Milwaukee in 2013. Since then he has been an active member in Professor Hossain group and has received multiple Chancellor's Fellowship Awards. He was awarded an ACS Milwaukee Section Travel Grant in 2018. He was also honored with the University’s Outstanding Teaching Assistant Award for 2017.

Documents

Discussion Addendum for: Convenient Preparation of 3 …orgsyn.org/Content/pdfs/procedures/v96p0098.pdf · 2019-04-12 · Org. Synth. 2019, 96, 98-109 99 DOI: 10.15227/orgsyn.096.0098