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Synthesis 2024; 56(22): 3488-3502
DOI: 10.1055/a-2367-2151
DOI: 10.1055/a-2367-2151
paper
Ring-Closing Metathesis as Methodology for the Synthesis of 2- and 3-Arylbenzo[b]furans
This work is based on research supported by the University of the Free State and the National Research Foundation of South Africa. The authors acknowledge that opinions, findings, and conclusions or recommendations expressed in any publication generated by the NRF-supported research is that of the authors alone, and that the NRF accepts no liability whatsoever in this regard.
Abstract
Olefin metathesis, which is well established in the petrochemical industry, is also emerging as a green technology in the manufacture of pharmaceutical and specialty chemicals. Arylbenzofurans are of interest for potential medicinal applications. In this paper we report on the synthesis of various 2-aryl- and 3-arylbenzo[b]furans with natural substitution patterns from readily available starting materials in a strategy that applies ring-closing metathesis with the Grubbs second generation catalyst as key step.
Key words
arylbenzofurans - metathesis - Grubbs catalyst - allylation - Tebbe methylenation - Grignard reagent - Al(OTf)3Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2367-2151.
- Supporting Information
Publication History
Received: 05 June 2024
Accepted after revision: 16 July 2024
Accepted Manuscript online:
16 July 2024
Article published online:
13 August 2024
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References
- 1a Dwarakanath D, Gaonkar SL. Asian J. Org. Chem. 2022; 11: e202200282
- 1b Hiremathad A, Patil MR, Chethana KR, Chand K, Santos MA, Keri RS. RSC Adv. 2015; 5: 96809
- 1c Nevagi RJ, Dighe SN, Dighe SN. Eur. J. Med. Chem. 2015; 97: 561
- 1d Radadiya A, Shah A. Eur. J. Med. Chem. 2015; 97: 356
- 1e Miao Y.-H, Hu Y.-H, Yang J, Liu T, Sun J, Wang X.-J. RSC Adv. 2019; 9: 27510
- 2 Abbas AA, Dawood KM. RSC Adv. 2023; 13: 11096
- 3a Abu-Hashem AA, Hussein HA. R, Aly AS, Gouda MA. Synth. Commun. 2014; 44: 2285
- 3b Abdel-Wahab BF, Abdel-Aziz HA, Ahmed EM. Arch. Pharm. Chem. Life Sci. 2008; 341: 734
- 4 Naik R, Harmalkar DS, Xu X, Jang K, Lee K. Eur. J. Med. Chem. 2015; 90: 379
- 5 Zheng X.-K, Cao Y-G, Ke Y.-Y, Zhang Y.-L, Li F, Gong J.-H, Zhao X, Kuang H.-X, Feng W.-S. Phytochemistry 2017; 135: 128
- 6a Brady WT, Giang YF. J. Org. Chem. 1986; 51: 2145
- 6b Brady WT, Giang Y.-SF, Marchand AP, Wu A.-H. J. Org. Chem. 1987; 52: 3457
- 7a Date M, Kawanishi K, Hori T, Watanabe M, Furukawa S. Chem. Pharm. Bull. 1989; 37: 2884
- 7b Watanabe M, Kawanishi K, Furukawa S. Chem. Pharm. Bull. 1991; 39: 579
- 7c Kanvinde MN, Kelkar RM, Paradkar MV. Synth. Commun. 1993; 23: 961
- 7d Chen C.-Y, Dormer PG. J. Org. Chem. 2005; 70: 6964
- 7e Ruan L, Shi M, Mao S, Yu L, Yang F, Tang J. Tetrahedron 2014; 70: 1065
- 8a Mushtaq A, Zahoor AF, Ahmad S, Saif MJ, Ul Haq A, Khan SG, Al-Mutairi AA, Irfan A, Al-Hussain SA, Zaki ME. A. ACS Omega 2024; 9: 20728
- 8b Heravi MM, Zadsirjan V. Recent Advances in the Synthesis of Benzo[b]furans . In Advances in Heterocyclic Chemistry, Vol. 143. Scriven EF. V, Ramsden CA. Academic Press; London: 2024: 177-226
- 9a Sawatzky RS, Stradiotto M. Synlett 2018; 29: 799
- 9b Mayhugh AL, Luscombe CK. Org. Lett. 2021; 23: 7079
- 9c Hegde RV, Ong T.-G, Ambre R, Jadhav AH, Patil SA, Dateer RB. Catal. Lett. 2021; 151: 1397
- 9d Cao J, Chen Z.-L, Li S.-M, Zhu G.-F, Yang Y.-Y, Wang C, Chen W.-Z, Wang J.-T, Zhang J.-Q, Tang L. Eur. J. Org. Chem. 2018; 2774
- 9e Hess A, Alandini N, Guelen HC, Prohaska JP, Knochel P. Chem. Commun. 2022; 58: 8774
- 9f Yao J, Shao L, Kang X, Zhu M, Huo X, Wang X. J. Org. Chem. 2024; 89: 1719
- 10a Sinai A, Mészáros A, Balogh A, Zwillinger M, Novák Z. Synthesis 2017; 49: 2374
- 10b Wang Y, Zhou C, Wang R. Green Chem. 2015; 17: 3910
- 10c Boyer A, Isono N, Lackner S, Lautens M. Tetrahedron 2010; 66: 6468
- 10d Auzias MG, Neuburger M, Wegner HA. Synlett 2010; 2443
- 10e Watanabe K, Mino T, Ishikawa E, Masudo C, Yoshida Y, Sakamoto M. Org. Biomol. Chem. 2018; 16: 575
- 11 Zheng H.-X, Shan X.-H, Qu J.-P, Kang Y.-B. Org. Lett. 2018; 20: 3310
- 12a Kim I, Lee S.-H, Lee S. Tetrahedron Lett. 2008; 49: 6579
- 12b Kim I, Choi J. Org. Biomol. Chem. 2009; 7: 2788
- 12c Kim K, Kim I. Org. Lett. 2010; 12: 5314
- 13 Kraus GA, Schroeder JD. Synlett 2005; 16: 2504
- 14 Nicolaou KC, Snyder SA, Bigot A, Pfefferkorn JA. Angew. Chem. Int. Ed. 2000; 39: 1093
- 15 Zhao B, Lu X. Org. Lett. 2006; 8: 5987
- 16a Pieterse T, Marais C, Bezuidenhoudt BC. B. ARKIVOC 2022; (v): 98
- 16b Pieterse T, Marais C, Bezuidenhoudt BC. B. ARKIVOC 2022; (v): 217
- 16c Pieterse T, Marais C, Bezuidenhoudt BC. B. ARKIVOC 2023; (viii): 202311990
- 16d Pieterse T. PhD Thesis. University of the Free State; South Africa: 2017
- 16e Visser M. M.Sc. Dissertation. University of the Free State; South Africa: 2019
- 16f Kotha S, Solanke BU, Gupta NK. J. Mol. Struct. 2021; 1244: 130907
- 16g Kotha S, Solanke BU. Chem. Asian J 2022; 17: e202200084
- 17a Martín Castro AM. Chem. Rev 2004; 104: 2939
- 17b Klyuchareva EV, Ershova EV, Nigmatullina RG, Vozhdaeva MY, Kantor EA. Dokl. Chem. 2009; 424: 52
- 18a Kuznik N, Krompiec S. Coord. Chem. Rev. 2007; 251: 222
- 18b Wakamatsu H, Nishida M, Adachi N, Mori M. J. Org. Chem. 2000; 65: 3966
- 19a Tebbe FN, Guggenberger LJ. J. Chem. Soc., Chem. Commun. 1973; 227
- 19b Pine SH, Kim V, Lee V. Org. Synth. 1990; 69: 72
- 19c Nicolaou KC, Postema MH. D, Claiborne CF. J. Am. Chem. Soc. 1996; 118: 1565
- 19d Miller BJ, Pieterse T, Marais C, Bezuidenhoudt BC. B. Tetrahedron Lett. 2012; 53: 4708
- 20a Matsubara S, Sugihara M, Utimoto K. Synlett 1998; 313
- 20b Haahr A, Rankovic Z, Hartley RC. Tetrahedron Lett. 2011; 52: 3020
- 21 Fujimura O, Fu GC, Grubbs RH. J. Org. Chem. 1994; 59: 4029
- 22 Pieterse T, Visser M, Marais C, Bezuidenhoudt BC. B. Synlett 2016; 27: 1541
- 23 Chang RK, Clairmont BP, Lin S, Roy MacArthur AH. Organometallics 2019; 38: 4448
- 24 Kato E, Kawabata J. Bioorg. Med. Chem. Lett. 2010; 20: 4333
- 25 Wootton RC. R. Ph.D. Thesis. University of Salford; UK: 2000
- 26 Li S.-R, Chen H.-M, Chen P.-Y, Tsai J.-C, Chen L.-Y, Wang E.-C, Huang Y.-T, Wei Y.-C, Lu P.-J. J. Chin. Chem. Soc. 2008; 55: 923
- 27 Sasano K, Takaya J, Iwasawa N. J. Am. Chem. Soc. 2013; 135: 10954
- 28 Wang Z, Ai F, Wang Z, Zhao W, Zhu G, Lin Z, Sun J. J. Am. Chem. Soc. 2015; 137: 383
- 29 Geary LM, Hultin PG. Org. Lett. 2009; 11: 5478
- 30 Masagalli JN, BasavanaGowda MK, Chae H.-S, Choi WJ. Molecules 2021; 26: 1327
- 31 Wang H.-S, Chan C.-K, Chang M.-Y. Tetrahedron 2016; 72: 5132
- 32 Arias L, Vara Y, Cossio FP. J. Org. Chem. 2012; 77: 266
- 33 Chatterjea JN, Sinha AK, Lal S. J. Indian Chem. Soc. 1979; 56: 508