Login Register Cart 0
Generic placeholder image

Current Green Chemistry

Editor-in-Chief

ISSN (Print): 2213-3461
ISSN (Online): 2213-347X

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Mini-Review Article

Unlocking the Potential: A Comprehensive Review for the Synthesis of Benzofuran Derivatives

Author(s): Krina Patel, Heli Patel, Drashti Shah, Dharti Patel, Neel Savaliya, Tushar Bambharoliya, Ashish Shah, Anjali Mahavar and Ashish Patel*

Volume 11, Issue 1, 2024

Published on: 13 November, 2023

Page: [12 - 36] Pages: 25

DOI: 10.2174/0122133461272081231102061911

Price: $65

Abstract

Benzofuran, a versatile heterocyclic compound, has gained considerable attention in recent years due to its diverse biological activities, distinctive structural characteristics, broad synthetic approaches, and extensive applications. The growing potential inherent in benzofuran encourages many researchers to address the challenges of the synthesis of its framework. This comprehensive review aims to provide a detailed overview of the recent advancements in the synthesis of diverse benzofuran derivatives, highlighting innovative strategies, synthetic methodologies, and significant breakthroughs in the field. The synthetic methodologies are classified as metalcatalyzed routes, green-solvent-based routes, microwave-assisted methods, catalyst-free and solvent- free methods, and a miscellaneous group of routes. This categorization in review provides an easy means for the reader to rationally select the best possible synthetic method for benzofuran derivatives. In addition, it explores the use of different solvents and catalysts in benzofuran synthesis, which serves as a valuable resource for chemists, researchers, and scientists involved in pharmaceutical and allied sciences. Overall, this review provides a comprehensive overview of the synthesis of benzofuran scaffolds and complies with all the significant developments in the synthetic routes of benzofuran, which will be useful for researchers interested in the development of new benzofuran-based molecules.

Keywords: Benzofuran, heterocyclic chemistry, synthetic methodologies, ubiquitous fragment, benzofuran- based molecules.

« Previous Next »
Graphical Abstract

[1]
Gidron, O. Diskin-Posner, Y.; Bendikov, M. α-Oligofurans. J. Am. Chem. Soc., 2010, 132(7), 2148-2150.
[http://dx.doi.org/10.1021/ja9093346] [PMID: 20121137]
[2]
Heaney, H.; Katrizky, A.R.; Rees, C.W.; Scriven, E.F.V. Comprehensive Heterocyclic Chemistry; Pergamon: New York, 1996.
[3]
Kamal, M.; Shakya, A.K.; Jawaid, T. Benzofurans: A new profile of biological activities. Int. J. Med. Pharm. Sci., 2011, 1(3), 1-15.
[4]
De Luca, L.; Nieddu, G.; Porcheddu, A.; Giacomelli, G. Some recent approaches to the synthesis of 2-substituted benzofurans. Curr. Med. Chem., 2009, 16(1), 1-20.
[http://dx.doi.org/10.2174/092986709787002826] [PMID: 19149560]
[5]
Radadiya, A.; Shah, A. Bioactive benzofuran derivatives: An insight on lead developments, radioligands and advances of the last decade. Eur. J. Med. Chem., 2015, 97, 356-376.
[http://dx.doi.org/10.1016/j.ejmech.2015.01.021] [PMID: 25703339]
[6]
Proksch, P.; Rodriguez, E. Chromenes and benzofurans of the asteraceae, their chemistry and biological significance. Phytochemistry, 1983, 22(11), 2335-2348.
[http://dx.doi.org/10.1016/0031-9422(83)80118-6]
[7]
Kirilmis, C.; Ahmedzade, M.; Servi, S.; Koca, M.; Kizirgil, A.; Kazaz, C. Synthesis and antimicrobial activity of some novel derivatives of benzofuran: Part 2. The synthesis and antimicrobial activity of some novel 1-(1-benzofuran-2-yl)-2-mesitylethanone derivatives. Eur. J. Med. Chem., 2008, 43(2), 300-308.
[http://dx.doi.org/10.1016/j.ejmech.2007.03.023] [PMID: 17513022]
[8]
Abdel-Wahab, B.F.; Abdel-Aziz, H.A.; Ahmed, E.M. Convenient synthesis and antimicrobial activity of new 3-substituted 5-(benzofuran-2-yl)-pyrazole derivatives. Arch. Pharm. , 2008, 341(11), 734-739.
[http://dx.doi.org/10.1002/ardp.200800119] [PMID: 18816590]
[9]
Halabalaki, M.; Aligiannis, N.; Papoutsi, Z.; Mitakou, S.; Moutsatsou, P.; Sekeris, C.; Skaltsounis, A.L. Three new arylobenzofurans from onobrychis ebenoides and evaluation of their binding affinity for the estrogen receptor. J. Nat. Prod., 2000, 63(12), 1672-1674.
[http://dx.doi.org/10.1021/np000071b] [PMID: 11141112]
[10]
Gfesser, G.A.; Faghih, R.; Bennani, Y.L.; Curtis, M.P.; Esbenshade, T.A.; Hancock, A.A.; Cowart, M.D. Structure–activity relationships of arylbenzofuran H3 receptor antagonists. Bioorg. Med. Chem. Lett., 2005, 15(10), 2559-2563.
[http://dx.doi.org/10.1016/j.bmcl.2005.03.047] [PMID: 15863316]
[11]
Kozikowski, A.P.; Ma, D.; Du, L.; Lewin, N.E.; Blumberg, P.M. Effect of alteration of the heterocyclic nucleus of ILV on its isoform selectivity for PKC-palladium-catalyzed route to benzofuran analogs of ILV. J. Am. Chem. Soc., 1995, 117(25), 6666-6672.
[http://dx.doi.org/10.1021/ja00130a003]
[12]
Saku, O.; Saki, M.; Kurokawa, M.; Ikeda, K.; Takizawa, T.; Uesaka, N. Synthetic studies on selective adenosine A2A receptor antagonists: Synthesis and structure–activity relationships of novel benzofuran derivatives. Bioorg. Med. Chem. Lett., 2010, 20(3), 1090-1093.
[http://dx.doi.org/10.1016/j.bmcl.2009.12.028] [PMID: 20034788]
[13]
Mane, B.Y.; Agasimundin, Y.S.; Shivakumar, B. Synthesis of benzofuran analogs of fenamates as non-steroidal antiinflammatory agents. Indian J. Chem., 2010, 49(2), 264-269.
[14]
Gammill, R.B.; Day, C.E.; Schurr, P.E. Khellin analogs. 1. general topological requirements for lipid-altering activity in furochromones. J. Med. Chem., 1983, 26(12), 1672-1674.
[http://dx.doi.org/10.1021/jm00366a002] [PMID: 6644736]
[15]
Schneiders, G.E.; Stevenson, R. Synthesis of (.+-.)-machicendiol. J. Org. Chem., 1979, 44(25), 4710-4711.
[http://dx.doi.org/10.1021/jo00393a055]
[16]
Ana, J.S.; Alves, S.; José, A.; Pereira, A.; Dethoup, T.; Cravo, S.; Mistry, S.; Artur, M.; Silva, M.S.; Madalena, M.; Pinto, M.; Anake, K. A new meroterpene, a new benzofuran derivative and other constituents from cultures of the marine sponge-associated fungus Acremonium persicinum KUFA 1007 and Their Anticholinesterase Activities. Mar. Drugs, 2019, 17, 379.
[17]
Jedrych, Z.; Borkowska, G. Investigation of new benzofurane, benzopiran and furanochromone derivatives--potential antiarrhythmic and hypotensive agents. Pol. J. Pharmacol. Pharm., 1983, 35(5), 397-403.
[PMID: 6664941]
[18]
Afosah, D.K.; Verespy, S., III; Al-Horani, R.A.; Boothello, R.S.; Karuturi, R.; Desai, U.R. A small group of sulfated benzofurans induces steady-state submaximal inhibition of thrombin. Bioorg. Med. Chem. Lett., 2018, 28(6), 1101-1105.
[http://dx.doi.org/10.1016/j.bmcl.2018.01.069] [PMID: 29459207]
[19]
Messina, F.; Botta, M.; Corelli, F.; Mugnaini, C. Chiral azole derivatives, 3. Synthesis of the enantiomers of the potent aromatase inhibitor 1-[2-benzofuranyl(4-chlorophenyl)methyl]-1H-imidazole. Tetrahedron Lett., 1999, 40(40), 7289-7292.
[http://dx.doi.org/10.1016/S0040-4039(99)01569-5]
[20]
Singh, B.N.; Williams, M.V. The effect of amiodarone, a new anti-anginal drug, on cardiac muscle. Br. J. Pharmacol., 1970, 39(4), 657-667.
[http://dx.doi.org/10.1111/j.1476-5381.1970.tb09891.x] [PMID: 5485142]
[21]
Smith, R.A.; Chen, J.; Mader, M.M.; Muegge, I.; Moehler, U.; Katti, S.; Marrero, D.; Stirtan, W.G.; Weaver, D.R.; Xiao, H.; Carley, W. Solid-Phase synthesis and investigation of benzofurans as selective estrogen receptor modulators. Bioorg. Med. Chem. Lett., 2002, 12(20), 2875-2878.
[http://dx.doi.org/10.1016/S0960-894X(02)00613-3] [PMID: 12270167]
[22]
Chawla, H.P.S.; Grover, P.K.; Anand, N.; Kamboj, V.P.; Kar, A.B. Antifertility agents. IV. 2,3-Diphenylbenzo- and 5,6-polymethylene-benzofurans, 1,2-diphenylnaphthofurans, and some related compounds. J. Med. Chem., 1970, 13(1), 54-59.
[http://dx.doi.org/10.1021/jm00295a015] [PMID: 5412117]
[23]
Mazurov, A.A.; Kombo, D.C.; Hauser, T.A.; Miao, L.; Dull, G.; Genus, J.F.; Fedorov, N.B.; Benson, L.; Sidach, S.; Xiao, Y.; Hammond, P.S.; James, J.W.; Miller, C.H.; Yohannes, D. Discovery of (2S, 3R)- N-[2-(pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]oct-3-yl]benzo[b]furan-2-carboxamide (TC-5619), a selective α7 nicotinic acetylcholine receptor agonist, for the treatment of cognitive disorders. J. Med. Chem., 2012, 55(22), 9793-9809.
[http://dx.doi.org/10.1021/jm301048a]
[24]
Galal, S.A.; Abd El-All, A.S.; Abdallah, M.M.; El-Diwani, H.I. Synthesis of potent antitumor and antiviral benzofuran derivatives. Bioorg. Med. Chem. Lett., 2009, 19(9), 2420-2428.
[http://dx.doi.org/10.1016/j.bmcl.2009.03.069] [PMID: 19345581]
[25]
Dai, J.R.; Hallock, Y.F.; Cardellina, J.H., II; Boyd, M.R. HIV-inhibitory and cytotoxic oligostilbenes from the leaves of Hopea malibato. J. Nat. Prod., 1998, 61(3), 351-353.
[http://dx.doi.org/10.1021/np970519h] [PMID: 9544565]
[26]
Dean, F.M. The total synthesis of natural products. In: The total synthesis of naturally occurring oxygen ring componds; ApSimon, J; Wiley: New York, 1973.
[27]
Xu, X.; Yang, Y.; Mo, X.; Wei, J.; Zhang, X.; You, Q. Design, synthesis, and evaluation of benzofuran derivatives as novel anti-pancreatic carcinoma agents via interfering the hypoxia environment by targeting HIF-1α pathway. Eur. J. Med. Chem., 2017, 137, 45-62.
[http://dx.doi.org/10.1016/j.ejmech.2017.05.042] [PMID: 28554092]
[28]
Khanam, H. Shamsuzzaman, Bioactive Benzofuran derivatives: A review. Eur. J. Med. Chem., 2015, 97, 483-504.
[http://dx.doi.org/10.1016/j.ejmech.2014.11.039] [PMID: 25482554]
[29]
Jung, J.W.; Park, J.H.; Seo, K.H.; Oh, E.J.; Lee, D.Y.; Lim, D.W.; Han, D.; Song, M.C.; Baek, N.I. New hydroxy fatty acid from the root bark of Morus alba L. J. Korean Soc. Appl. Biol. Chem., 2015, 58(4), 541-543.
[http://dx.doi.org/10.1007/s13765-015-0071-5]
[30]
Liang, Z.; Xu, H.; Tian, Y.; Guo, M.; Su, X.; Guo, C. Design, synthesis and antifungal activity of novel benzofuran-triazole hybrids. Molecules, 2016, 21(6), 732-432.
[http://dx.doi.org/10.3390/molecules21060732] [PMID: 27338311]
[31]
Kenchappa, R.; Bodke, Y.D.; Telkar, S.; Aruna Sindhe, M. Antifungal and anthelmintic activity of novel benzofuran derivatives containing thiazolo benzimidazole nucleus: an in vitro evaluation. J. Chem. Biol., 2017, 10(1), 11-23.
[http://dx.doi.org/10.1007/s12154-016-0160-x] [PMID: 28101251]
[32]
Chand, K. A review on antioxidant potential of bioactive hetrocycle benzofuran: Natural and synthetic derivatives. Pharmacol. Rep., 2017, 69, 281-295.
[http://dx.doi.org/10.1016/j.pharep.2016.11.007] [PMID: 28171830]
[33]
Aswathanarayanappa, C.; Bheemappa, E.; Bodke, Y.D.; Bhovi, V.K.; Ningegowda, R.; Shivakumar, M.C.; Peethambar, S.K.; Telkar, S. 5-phenyl-1-benzofuran-2-yl derivatives: Synthesis, antimicrobial, and antioxidant activity. Med. Chem. Res., 2013, 22(1), 78-87.
[http://dx.doi.org/10.1007/s00044-012-0017-y]
[34]
Abdel-motaal, M.; Kandeel, E.M.; Abou-Elzahab, M.; Elghareeb, F. Synthesis and evaluation of antioxidant activity of some new hetrocyclic compounds bearing the benzo[b]furan moiety. Eur. Sci. J., 2017, 13(30), 297-313.
[http://dx.doi.org/10.19044/esj.2017.v13n30p297]
[35]
Rangaswamy, J.; Vijay Kumar, H.; Harini, S.T.; Naik, N. Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: As a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility. Bioorg. Med. Chem. Lett., 2012, 22(14), 4773-4777.
[http://dx.doi.org/10.1016/j.bmcl.2012.05.061] [PMID: 22695127]
[36]
Hiremathad, A.; Chand, K.; Keri, R.S. Development of coumarin–benzofuran hybrids as versatile multitargeted compounds for the treatment of Alzheimer’s Disease. Chem. Biol. Drug Des., 2018, 92(2), 1497-1503.
[http://dx.doi.org/10.1111/cbdd.13316] [PMID: 29679445]
[37]
Thévenin, M.; Thoret, S.; Grellier, P.; Dubois, J. Synthesis of polysubstituted benzofuran derivatives as novel inhibitors of parasitic growth. Bioorg. Med. Chem., 2013, 21(17), 4885-4892.
[http://dx.doi.org/10.1016/j.bmc.2013.07.002] [PMID: 23902828]
[38]
Stefano, R.; Céline, R.; Lorna, P.; Alessandra, B.; Silvia, G.; Manuela, B.; Vincenza, A.; Fabiana, M.; Andrea, T.; Jean-Pierre, M.; Angela, R. J. Med. Chem., 2008, 51, 2883-2886.
[http://dx.doi.org/10.1021/jm8002747] [PMID: 18419109]
[39]
Xie, Y.S.; Kumar, D.; Bodduri, V.D.V.; Tarani, P.S.; Zhao, B-X.; Miao, J-Y.; Jang, K.; Shin, D-S. Microwave-assisted parallel synthesis of benzofuran-2-carboxamide derivatives bearing anti-inflammatory, analgesic and antipyretic agents. Tetrahedron Lett., 2014, 55(17), 2796-2800.
[http://dx.doi.org/10.1016/j.tetlet.2014.02.116]
[40]
Yadav, P.; Singh, P.; Tewari, A.K. Design, synthesis, docking and anti-inflammatory evaluation of novel series of benzofuran based prodrugs. Bioorg. Med. Chem. Lett., 2014, 24(10), 2251-2255.
[http://dx.doi.org/10.1016/j.bmcl.2014.03.087] [PMID: 24745964]
[41]
Gans, K.R.; Galbraith, W.; Roman, R.J.; Haber, S.B.; Kerr, J.S.; Schmidt, W.K.; Smith, C.; Hewes, W.E.; Ackerman, N.R. Anti-inflammatory and safety profile of DuP 697, a novel orally effective prostaglandin synthesis inhibitor. J. Pharmacol. Exp. Ther., 1990, 254(1), 180-187.
[PMID: 2366180]
[42]
Lau, C.K.; Bélanger, P.C.; Dufresne, C.; Scheigetz, J.; Therien, M.; Fitzsimmons, B.; Young, R.N.; Ford-Hutchinson, A.W.; Riendeau, D.; Denis, D.; Guay, J.; Charleson, S.; Piechuta, H.; McFarlane, C.S.; Chiu, L. Development of 2,3-dihydro-6-(3-phenoxypropyl)-2-(2-phenylethyl)-5-benzofuranol (L-670,630) as a potent and orally active inhibitor of 5-lipoxygenase. J. Med. Chem., 1992, 35(7), 1299-1318.
[http://dx.doi.org/10.1021/jm00085a019] [PMID: 1313879]
[43]
Higashi, A.; Kishikawa, N.; Ohyama, K.; Kuroda, N. A simple and highly selective fluorescent sensor for palladium based on benzofuran-2-boronic acid. Tetrahedron Lett., 2017, 58(28), 2774-2778.
[http://dx.doi.org/10.1016/j.tetlet.2017.06.005]
[44]
Gupta, S.; Adhikary, S.; Modukuri, R.K.; Choudhary, D.; Trivedi, R.; Sashidhara, K.V. Benzofuran-pyran hybrids: A new class of potential bone anabolic agents. Bioorg. Med. Chem. Lett., 2018, 28(10), 1719-1724.
[http://dx.doi.org/10.1016/j.bmcl.2018.04.041] [PMID: 29703629]
[45]
Dudley, M.E.; Morshed, M.M.; Hossain, M.M. A convenient method of synthesizing 3-ethoxycarbonylbenzofurans from salicylaldehydes and ethyl diazoacetate. Synthesis, 2006, 10, 1711-1714.
[46]
Dawood, K.M.; Abdel-Gawad, H.; Rageb, E.A.; Ellithey, M.; Mohamed, H.A. Synthesis, anticonvulsant, and anti-inflammatory evaluation of some new benzotriazole and benzofuran-based heterocycles. Bioorg. Med. Chem., 2006, 14(11), 3672-3680.
[http://dx.doi.org/10.1016/j.bmc.2006.01.033] [PMID: 16464601]
[47]
Ryu, C.K.; Song, A.L.; Lee, J.Y.; Hong, J.A.; Yoon, J.H.; Kim, A. Synthesis and antifungal activity of benzofuran-5-ols. Bioorg. Med. Chem. Lett., 2010, 20(22), 6777-6780.
[http://dx.doi.org/10.1016/j.bmcl.2010.08.129] [PMID: 20851600]
[48]
Telvekar, V.N.; Belubbi, A.; Bairwa, V.K.; Satardekar, K. Novel N′-benzylidene benzofuran-3-carbohydrazide derivatives as antitubercular and antifungal agents. Bioorg. Med. Chem. Lett., 2012, 22(6), 2343-2346.
[http://dx.doi.org/10.1016/j.bmcl.2012.01.067] [PMID: 22365752]
[49]
Nosova, É.V.; Kravchenko, M.A.; Lipunova, G.N.; Chasovskikh, O.M.; Sokolov, V.A.; Charushin, V.N. Synthesis and antituberculous activity of fluorinated 3-R-hydrazino2-benzoylacrylates and their cyclization products. Pharm. Chem. J., 2002, 36(11), 585-587.
[http://dx.doi.org/10.1023/A:1022657029905]
[50]
Fuganti, C.; Serra, S. A new approach to 2-aryl-7-alkoxy-benzofurans: Synthesis of ailanthoidol, a natural neolignan. Tetrahedron Lett., 1998, 39(31), 5609-5610.
[http://dx.doi.org/10.1016/S0040-4039(98)01053-3]
[51]
Asif, M. Mini review on important biological properties of benzofuran derivatives. J. Anal. Pharm. Res., 2016, 3(2), 1-4.
[http://dx.doi.org/10.15406/japlr.2016.03.00050]
[52]
Liang, Y.; Tao, L-M.; Zhang, Y-H.; Li, J-H. Palladium-catalyzed cross-coupling reactions of 1,2-diiodoalkenes with terminal alkynes: Selective synthesis of unsymmetrical buta-1,3-diynes and 2-ethynylbenzofurans. Synthesis, 2008, 24, 3988-3994.
[53]
Chen, C.; Dormer, P.G. Synthesis of Benzo[ b ]furans via CuI-Catalyzed Ring Closure. J. Org. Chem., 2005, 70(17), 6964-6967.
[http://dx.doi.org/10.1021/jo050788+] [PMID: 16095327]
[54]
Kumar, K.S.; Adepu, R.; Kapavarapu, R.; Rambabu, D.; Krishna, G.R.; Reddy, C.M.; Priya, K.K.; Parsa, K.V.L.; Pal, M. AlCl3 induced C-arylation/cyclization in a single pot: A new route to benzofuran fused N-heterocycles of pharmacological interest. Tetrahedron Lett., 2012, 53(9), 1134-1138.
[http://dx.doi.org/10.1016/j.tetlet.2011.12.096]
[55]
Katritzky, A.R.; Fali, C.N.; Li, J. General synthesis of polysubstituted benzo[b]furans. J. Org. Chem., 1997, 62(23), 8205-8209.
[http://dx.doi.org/10.1021/jo9710846] [PMID: 11671934]
[56]
Zhou, L.; Shi, Y.; Xiao, Q.; Liu, Y.; Ye, F.; Zhang, Y.; Wang, J. CuBr-catalyzed coupling of N-tosylhydrazones and terminal alkynes: Synthesis of benzofurans and indoles. Org. Lett., 2011, 13(5), 968-971.
[http://dx.doi.org/10.1021/ol103009n] [PMID: 21268646]
[57]
Wang, J.R.; Manabe, K. Hydroxyterphenylphoshine-palladium catalyst for benzo[b]furan synthesis from 2-chlorophenols. bifunctional ligand strategy for cross-coupling of chloroarenes. J. Org. Chem., 2010, 75(15), 5340-5342.
[http://dx.doi.org/10.1021/jo1007948] [PMID: 20578763]
[58]
Kumar, M.P.; Liu, R.S. Zn(OTf)2-catalyzed cyclization of proparyl alcohols with anilines, phenols, and amides for synthesis of indoles, benzofurans, and oxazoles through different annulation mechanisms. J. Org. Chem., 2006, 71(13), 4951-4955.
[http://dx.doi.org/10.1021/jo0606711] [PMID: 16776526]
[59]
Hirano, K.; Satoh, T.; Miura, M. Copper-catalyzed annulative amination of ortho-alkynylphenols with hydroxylamines: Synthesis of 3-aminobenzofurans by umpolung amination strategy. Org. Lett., 2011, 13(9), 2395-2397.
[http://dx.doi.org/10.1021/ol200651r] [PMID: 21449554]
[60]
van Otterlo, W.A.L.; Morgans, G.L.; Madeley, L.G.; Kuzvidza, S.; Moleele, S.S.; Thornton, N.; de Koning, C.B. An isomerization-ring-closing metathesis strategy for the synthesis of substituted benzofurans. Tetrahedron, 2005, 61(32), 7746-7755.
[http://dx.doi.org/10.1016/j.tet.2005.05.090]
[61]
Maimone, T.J.; Buchwald, S.L. Pd-catalyzed O-arylation of ethyl acetohydroximate: synthesis of O-arylhydroxylamines and substituted benzofurans. J. Am. Chem. Soc., 2010, 132(29), 9990-9991.
[http://dx.doi.org/10.1021/ja1044874] [PMID: 20604520]
[62]
Nakamura, I.; Mizushima, Y.; Yamamoto, Y. Synthesis of 2,3-disubstituted benzofurans by platinum-olefin-catalyzed carboalkoxylation of o-alkynylphenyl acetals. J. Am. Chem. Soc., 2005, 127(43), 15022-15023.
[http://dx.doi.org/10.1021/ja055202f] [PMID: 16248630]
[63]
Collini, M.D.; Kaufman, D.H.; Manas, E.S.; Harris, H.A.; Henderson, R.A.; Xu, Z.B.; Unwalla, R.J.; Miller, C.P. 7-Substituted 2-phenyl-benzofurans as ERβ selective ligands. Bioorg. Med. Chem. Lett., 2004, 14(19), 4925-4929.
[http://dx.doi.org/10.1016/j.bmcl.2004.07.029] [PMID: 15341953]
[64]
Cowart, M.; Pratt, J.K.; Stewart, A.O.; Bennani, Y.L.; Esbenshade, T.A.; Hancock, A.A. A new class of potent non-imidazole H3 antagonists: 2-aminoethylbenzofurans. Bioorg. Med. Chem. Lett., 2004, 14(3), 689-693.
[http://dx.doi.org/10.1016/j.bmcl.2003.11.032] [PMID: 14741270]
[65]
Thielges, S.; Meddah, E.; Bisseret, P.; Eustache, J. New synthesis of benzo[b]furan and indole derivatives from 1,1-dibromo-1-alkenes using a tandem Pd-assisted cyclization–coupling reaction. Tetrahedron Lett., 2004, 45(5), 907-910.
[http://dx.doi.org/10.1016/j.tetlet.2003.11.118]
[66]
Liao, Y.; Smith, J.; Fathi, R.; Yang, Z. Novel PdII-mediated cascade carboxylative annulation to construct benzo[b]furan-3-carboxylic acids. Org. Lett., 2005, 7(13), 2707-2709.
[http://dx.doi.org/10.1021/ol050876g] [PMID: 15957927]
[67]
Fürstner, A.; Davies, P.W. Heterocycles by PtCl2-catalyzed intramolecular carboalkoxylation or carboamination of alkynes. J. Am. Chem. Soc., 2005, 127(43), 15024-15025.
[http://dx.doi.org/10.1021/ja055659p] [PMID: 16248631]
[68]
Anderson, K.W.; Ikawa, T.; Tundel, R.E.; Buchwald, S.L. The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans. J. Am. Chem. Soc., 2006, 128(33), 10694-10695.
[http://dx.doi.org/10.1021/ja0639719] [PMID: 16910660]
[69]
Hwu, J.R.; Chuang, K.S.; Chuang, S.H.; Tsay, S.C. New benzo[b]furans as electroluminescent materials for emitting blue light. Org. Lett., 2005, 7(8), 1545-1548.
[http://dx.doi.org/10.1021/ol050196d] [PMID: 15816748]
[70]
Nakamura, M.; Ilies, L.; Otsubo, S.; Nakamura, E. 2,3-disubstituted benzofuran and indole by copper-mediated C-C bond extension reaction of 3-zinciobenzoheterole. Org. Lett., 2006, 8(13), 2803-2805.
[http://dx.doi.org/10.1021/ol060896y] [PMID: 16774261]
[71]
Botta, M.; Summa, V.; Corelli, F.; Di Pietro, G.; Lombardi, P. Synthesis of aryl 2-benzofuranyl and aryl 2-indolyl carbinols of high enantiomeric purity via palladium-catalyzed heteroannulation of chiral arylpropargylic alcohols. Tetrahedron Asymmetry, 1996, 7(5), 1263-1266.
[http://dx.doi.org/10.1016/0957-4166(96)00138-3]
[72]
Oppenheimer, J.; Johnson, W.L.; Tracey, M.R.; Hsung, R.P.; Yao, P.Y.; Liu, R.; Zhao, K. A rhodium(I)-catalyzed demethylation-cyclization of o-anisole-substituted ynamides in the synthesis of chiral 2-amido benzofurans. Org. Lett., 2007, 9(12), 2361-2364.
[http://dx.doi.org/10.1021/ol0707362] [PMID: 17489599]
[73]
Xiao, Q.; Xia, Y.; Li, H.; Zhang, Y.; Wang, J. Coupling of N-tosylhydrazones with terminal alkynes catalyzed by copper(I): synthesis of trisubstituted allenes. Angew. Chem. Int. Ed., 2011, 50(5), 1114-1117.
[http://dx.doi.org/10.1002/anie.201005741] [PMID: 21268207]
[74]
Wang, S.; Li, P.; Yu, L.; Wang, L. Sequential and one-pot reactions of phenols with bromoalkynes for the synthesis of (Z)-2-bromovinyl phenyl ethers and benzo[b]furans. Org. Lett., 2011, 13(22), 5968-5971.
[http://dx.doi.org/10.1021/ol202383z] [PMID: 22007879]
[75]
Ichake, S.S.; Konala, A.; Kavala, V.; Kuo, C.W.; Yao, C.F. Palladium-catalyzed tandem C-H functionalization/cyclization strategy for the synthesis of 5-hydroxybenzofuran derivatives. Org. Lett., 2017, 19(1), 54-57.
[http://dx.doi.org/10.1021/acs.orglett.6b03310] [PMID: 27958749]
[76]
Boyer, A.; Isono, N.; Lackner, S.; Lautens, M. Domino rhodium(I)-catalysed reactions for the efficient synthesis of substituted benzofurans and indoles. Tetrahedron, 2010, 66(33), 6468-6482.
[http://dx.doi.org/10.1016/j.tet.2010.05.106]
[77]
Thalji, R.K.; Aiyar, N.; Davenport, E.A.; Erhardt, J.A.; Kallal, L.A.; Morrow, D.M.; Senadhi, S.; Burns-Kurtis, C.L.; Marino, J.P. Jr Benzofuran-substituted urea derivatives as novel P2Y1 receptor antagonists. Bioorg. Med. Chem. Lett., 2010, 20(14), 4104-4107.
[http://dx.doi.org/10.1016/j.bmcl.2010.05.072] [PMID: 20542694]
[78]
Li, C.; Zhang, Y.; Li, P.; Wang, L. Palladium-catalyzed oxidative cyclization of 3-phenoxyacrylates: An approach to construct substituted benzofurans from phenols. J. Org. Chem., 2011, 76(11), 4692-4696.
[http://dx.doi.org/10.1021/jo200317f] [PMID: 21542613]
[79]
Luo, Y.; Wu, J. A new insight into palladium-catalyzed reaction of 2-alkynylphenol with carbon monoxide. Org. Lett., 2011, 13(21), 5858-5861.
[http://dx.doi.org/10.1021/ol202478u] [PMID: 21988411]
[80]
Yuan, W.; Ma, S. Benzofuran derivatives from alkynyl-substituted benzynes and aryl halides. Org. Lett., 2014, 16(1), 193-195.
[http://dx.doi.org/10.1021/ol4032254] [PMID: 24387317]
[81]
Bosiak, M.J. A convenient synthesis of 2-arylbenzo[b]furans from aryl halides and 2-halophenols by catalytic one-pot cascade method. ACS Catal., 2016, 6(4), 2429-2434.
[http://dx.doi.org/10.1021/acscatal.6b00190]
[82]
Kumar, A.; Gangwar, M.K.; Prakasham, A.P.; Mhatre, D.; Kalita, A.C.; Ghosh, P. Accessing a biologically relevant benzofuran skeleton by a one-pot tandem heck alkynylation/cyclization reaction using well-defined palladium N-heterocyclic carbene complexes. Inorg. Chem., 2016, 55(6), 2882-2893.
[http://dx.doi.org/10.1021/acs.inorgchem.5b02727] [PMID: 26928799]
[83]
Shibata, T.; Hashimoto, Y.; Otsuka, M.; Tsuchikama, K.; Endo, K. Ir(III)-catalyzed room-temperature synthesis of multisubstituted benzofurans initiated by C-H activation of α-aryloxy ketones. Synlett, 2011, 2011(14), 2075-2079.
[http://dx.doi.org/10.1055/s-0030-1260981]
[84]
Ye, S.; Liu, G.; Pu, S.; Wu, J. Synthesis of 2-(polyfluoroaryl)benzofurans via a copper(I)-catalyzed reaction of 2-(2,2-dibromovinyl)phenol with polyfluoroarene. Org. Lett., 2012, 14(1), 70-73.
[http://dx.doi.org/10.1021/ol202858f] [PMID: 22136654]
[85]
Okamoto, R.; Okazaki, E.; Noguchi, K.; Tanaka, K. Rhodium-catalyzed olefin isomerization/enantioselective intramolecular Alder-ene reaction cascade. Org. Lett., 2011, 13(18), 4894-4897.
[http://dx.doi.org/10.1021/ol201986e] [PMID: 21866888]
[86]
Kanno, H.; Nakamura, K.; Noguchi, K.; Shibata, Y.; Tanaka, K. Rhodium-catalyzed cycloisomerization of 2-silylethynyl phenols and anilines via 1,2-silicon migration. Org. Lett., 2016, 18(7), 1654-1657.
[http://dx.doi.org/10.1021/acs.orglett.6b00529] [PMID: 27002692]
[87]
Miao, Y.; Hu, Y.; Yang, J.; Liu, T.; Sun, J.; Wang, X. Natural source, bioactivity and synthesis of benzofuran derivatives. RSC Advances, 2019, 9(47), 27510-27540.
[http://dx.doi.org/10.1039/C9RA04917G] [PMID: 35529241]
[88]
Burgstahler, A.W.; Worden, L.R.; Noland, W.E.; Parham, W.E.; Carol, W. Org. Synth.Coll., 1973, 5, 251.
[89]
Shang, Y.; Wang, C.; He, X.; Ju, K.; Zhang, M.; Yu, S.; Wu, J. DMAP-catalyzed cascade reaction: One-pot synthesis of benzofurans in water. Tetrahedron, 2010, 66(50), 9629-9633.
[http://dx.doi.org/10.1016/j.tet.2010.09.095]
[90]
Carril, M.; SanMartin, R.; Tellitu, I.; Domínguez, E. On-water chemistry: copper-catalyzed straightforward synthesis of benzo[b]furan derivatives in neat water. Org. Lett., 2006, 8(7), 1467-1470.
[http://dx.doi.org/10.1021/ol060274c] [PMID: 16562918]
[91]
Ghosh, S.; Das, J.; Saikh, F. A new synthesis of 2-aryl/alkylbenzofurans by visible light stimulated intermolecular Sonogashira coupling and cyclization reaction in water. Tetrahedron Lett., 2012, 53(44), 5883-5886.
[http://dx.doi.org/10.1016/j.tetlet.2012.08.078]
[92]
Rossy, C.; Fouquet, E.; Felpin, F.X. Practical synthesis of indoles and benzofurans in water using a heterogeneous bimetallic catalyst. Beilstein J. Org. Chem., 2013, 9, 1426-1431.
[http://dx.doi.org/10.3762/bjoc.9.160] [PMID: 23946838]
[93]
Devi, A.P.; Dhingra, N.; Chundawat, R.S.; Ameta, K.L. Green synthesis of 2-benzylidene-1-benzofuran-3-ones and in vitro neuraminidase study using molecular docking. SAR QSAR Environ. Res., 2022, 33(7), 499-512.
[http://dx.doi.org/10.1080/1062936X.2022.2087733] [PMID: 35735074]
[94]
Marriott, K.S.C.; Bartee, R.; Morrison, A.Z.; Stewart, L.; Wesby, J. Expedited synthesis of benzofuran-2-carboxylic acids via microwave-assisted Perkin rearrangement reaction. Tetrahedron Lett., 2012, 53(26), 3319-3321.
[http://dx.doi.org/10.1016/j.tetlet.2012.04.075] [PMID: 22736873]
[95]
De Luca, L.; Giacomelli, G.; Nieddu, G. A facile approach to the synthesis of chiral 2-substituted benzofurans. J. Org. Chem., 2007, 72(10), 3955-3957.
[http://dx.doi.org/10.1021/jo070142c] [PMID: 17419648]
[96]
Kumar, S.; Namkung, W.; Verkman, A.S.; Sharma, P.K. Novel 5-substituted benzyloxy-2-arylbenzofuran-3-carboxylic acids as calcium activated chloride channel inhibitors. Bioorg. Med. Chem., 2012, 20(14), 4237-4244.
[http://dx.doi.org/10.1016/j.bmc.2012.05.074] [PMID: 22739085]
[97]
Bogdal, D.; Warzala, M. Warzala, M. Microwave- assisted preparation of benzo[b]furans under solventless phase-transfer catalytic conditions. Tetrahedron, 2000, 56(44), 8769-8773.
[http://dx.doi.org/10.1016/S0040-4020(00)00818-8]
[98]
Sapkal, S.B.; Shelke, K.F.; Shingate, B.B.; Shingare, M.S. An efficient synthesis of benzofuran derivatives under conventional/non-conventional method. Chin. Chem. Lett., 2010, 21(12), 1439-1442.
[http://dx.doi.org/10.1016/j.cclet.2010.06.038]
[99]
Kabalka, G.W.; Wang, L.; Pagni, R.M. Sonogashira coupling and cyclization reactions on alumina: A route to aryl alkynes, 2-substituted-benzo[b]furans and 2-substituted-indoles. Tetrahedron, 2001, 57(38), 8017-8028.
[http://dx.doi.org/10.1016/S0040-4020(01)00774-8]
[100]
Murray, W.M.; Semple, J.E. Facile access to novel 1,4-dihydroxynapththalene-2,3- dicarboximides and heterofused analogues. Synthesis, 1996, 1996(10), 1180-1182.
[http://dx.doi.org/10.1055/s-1996-4372]
[101]
Pei, T.; Chen, C.; DiMichele, L.; Davies, I.W. Controlled synthesis of 2- and 3-substituted benzo[b]furans. Org. Lett., 2010, 12(21), 4972-4975.
[http://dx.doi.org/10.1021/ol102123u] [PMID: 20873816]
[102]
Huang, X.C.; Liu, Y.L.; Liang, Y.; Pi, S.F.; Wang, F.; Li, J.H. Cycloaddition of arynes with iodonium ylides: A mild and general route for the synthesis of benzofuran derivatives. Org. Lett., 2008, 10(8), 1525-1528.
[http://dx.doi.org/10.1021/ol800051k] [PMID: 18338899]
[103]
Zhang, Y.; Wang, Y. An efficient solid-phase synthesis of substituted benzofuran using selenium-bound resin. Appl. Organomet. Chem., 2012, 26(5), 212-216.
[http://dx.doi.org/10.1002/aoc.2840]
[104]
Riyahi, Z.; Asadi, P.; Hassanzadeh, F.; Khodamoradi, E.; Gonzalez, A.; Karimi A, M. Synthesis of novel conjugated benzofurantriazine derivatives: Antimicrobial and in silico molecular docking studies. Heliyon, 2023, 9(8), e18759.
[http://dx.doi.org/10.1016/j.heliyon.2023.e18759] [PMID: 37576200]
[105]
Mohammad, A. Catalyst –free synthesis of benzofuran derivatives from cascade reaction between nitroepoxides and salicyladehydes. J. Org. Chem., 2021, 86, 4756-4762.
[http://dx.doi.org/10.1021/acs.joc.1c00143] [PMID: 33656875]
[106]
Kalagara, S.P.N.R.; Baddam, S.R.A. Concise and catalyst free synthesis of 2,3-disubstituted dihydrobenzofuran-3-amines. SSRN, 2023, 1-5.
[107]
Yue, D.; Yao, T.; Larock, R.C. Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization. J. Org. Chem., 2005, 70(25), 10292-10296.
[http://dx.doi.org/10.1021/jo051299c] [PMID: 16323837]
[108]
Sun, L-Q.; Takaki, K.; Chen, J.; Iben, L.; Knipe, J.O.; Pajor, L.; Mahle, C.D.; Ryan, E.; Xu, C.N. -{2-[2-(4-phenylbutyl)benzofuran-4-yl]cyclopropylmethyl}acetamide: An orally bioavailable melatonin receptor antagonist. Bioorg. Med. Chem. Lett., 2004, 14, 5157-5160.
[http://dx.doi.org/10.1016/j.bmcl.2004.07.055] [PMID: 15380218]
[109]
Kraus, G.A.; Zhang, N.; Verkade, J.G.; Nagarajan, M.; Kisanga, P.B. Deprotonation of benzylic ethers using a hindered phosphazene base. A synthesis of benzofurans from ortho-substituted benzaldehydes. Org. Lett., 2000, 2(16), 2409-2410.
[http://dx.doi.org/10.1021/ol0000758] [PMID: 10956508]
[110]
Yao, T.; Yue, D.; Larock, R.C. Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization. J. Comb. Chem., 2005, 7, 809.
[http://dx.doi.org/10.1021/cc050062r] [PMID: 16283788]
[111]
Contiero, F.; Jones, K.M.; Matts, E.A.; Porzelle, A.; Tomkinson, N.C.O. Direct preparation of benzofurans from O arylhydroxylamines. Synlett, 2009, 18, 3003-3006.
[112]
Yu-hong, M.; Xiao-Yu, H.; Long, W.; Qing-Qing, Y. PPh3- triggered tandem synthesis of 2,3-disubstituted benzofuran derivatives from derivatives from o-Quinone methides with acyl chlorides. J. Org. Chem., 2022, 17, 11852-11856.
[113]
Yankun, L.; Chen-Ho, T.; Zhenghu, X. Synthesis of benzofuran derivatives via a gold- catalyzed claisen rearrangement cascade. Org. Lett., 2022, 31, 5829-5834.
[114]
Kitano, J.; Nishii, Y.; Miura, M. Selective synthesis of C4-functionalized benzofurans by rhodium- catalyzed vinylene transfer:Computational study on the cyclopentadienyl ligand. Org. Lett., 2022, 24(31), 5679-5683.
[http://dx.doi.org/10.1021/acs.orglett.2c02030] [PMID: 35900136]

Rights & Permissions Print Cite
Article Metrics
13
4
© 2024 Bentham Science Publishers | Privacy Policy