REVIEWS

Recent Progress in the Synthesis of Substituted Benzo[b]furan Derivatives

  • Zhihao Zhang ,
  • Xin Jiang ,
  • Qinghan Li
Expand
  • a College of Chemistry and Environment, Southwest Minzu University, Chengdu 610041
    b Key Laboratory of General Chemistry of the National Ethnic Affairs Commission, College of Chemistry and Environment, Southwest Minzu University, Chengdu 610041
    c Key Laboratory of pollution Control Chemistry and Environmental Functional Materials for Qinghai-Tibet Plateau of the National Ethnic Affairs Commission, College of Chemistry and Environment, Southwest Minzu University, Chengdu 610041
* E-mail:

Received date: 2021-10-08

  Revised date: 2021-11-20

  Online published: 2021-12-15

Supported by

Graduate Student Innovation Funds of Southwest Minzu University(CX2020SZ18); Sichuan Provincial Department of Science and Technology Support Program(2015NZ0033)

Abstract

Benzo[b]furan structure is found in many natural products and bioactive compounds. Benzo[b]furan derivatives have attracted the attention of pharmaceutical chemists because of their antiviral, anticancer, insecticidal and anti inflammatory, analgesic and antioxidant activities. At present, many effective synthetic methods have been reported and become one of the hot topics of organic synthesis research in recent years. The research progress in the synthesis of substituted benzo[b]furan derivatives by cyclization or coupling reaction under the conditions of transition metal catalysis and catalysts free in recent ten years is reviewed.

Cite this article

Zhihao Zhang , Xin Jiang , Qinghan Li . Recent Progress in the Synthesis of Substituted Benzo[b]furan Derivatives[J]. Chinese Journal of Organic Chemistry, 2022 , 42(4) : 945 -964 . DOI: 10.6023/cjoc202110008

References

[1]
Miao, Y. H.; Hu, Y. H.; Yang, J.; Liu, T.; Sun, J.; Wang, X. J. RSC Adv. 2019, 9, 27510.
[2]
Karagöz, A. Ç.; Reiter, C.; Seo, E. J. Bioorg. Med. Chem. 2018, 26, 3610.
[3]
Xu, X. L.; Yang, Y. R.; Mo, X. F.; Wei, J. L.; Zhang, X. J.; You, Q. D. Eur. J. Med. Chem. 2017, 137, 45.
[4]
Thévenin, M.; Thoret, S.; Grellier, P.; Dubois, J. Bioorg. Med. Chem. 2013, 21, 4885.
[5]
(a) Liang, Z.; Xu, H.; Tian, Y.; Guo, M.; Su, X.; Guo, C. Molecules 2016, 21, 732.
[5]
(b) Kenchappa, R.; Bodke, Y. D.; Telkar, S.; Sindhe, M. A. J. Chem. Biol. 2017, 10, 1.
[6]
Tan, Y. X.; Gong, T.; Liu, C. Chem. Pharm. Bull. 2010, 58, 579.
[7]
Aswathanarayanappa, C.; Bheemappa, E.; Bodke, Y. D.; Bhovi, V. K.; Ningegowda, R.; Shivakumar, M. C. Med. Chem. Res. 2012, 22, 78.
[8]
(a) Schroeter, F.; Soellner, J.; Thomas Strassner, T. ACS Catal. 2017, 7, 3004.
[8]
(b) Hamasaka, G.; Roy, D.; Tazawa, A.; Uozumi, Y. ACS Catal. 2019, 9, 11640.
[8]
(c) Chen, Z. K.; Wang, B. J.; Zhang, J. T.; Yu, W. L.; Liu, Z. X.; Zhang, Y. H. Org. Chem. Front. 2015, 2, 1107.
[9]
Liu, Y.; Yao, B.; Deng, C. L.; Tang, R. Y.; Zhang, X. G.; Li, J. H. Org. Lett. 2011, 13, 1126.
[10]
Geary, L. M.; Hultin, P. G. Eur. J. Org. Chem. 2010, 2010, 5563.
[11]
Liu, J.; Chen, W.; Ji, Y.; Wang, L. Adv. Synth. Catal. 2012, 354, 1585.
[12]
Rehan, M.; Nallagonda, R.; Das, B. G.; Meena, T.; Ghorai, P. J. Org. Chem. 2017, 82, 3411.
[13]
Yamaguchi, M.; Ozawa, H.; Katsumata, H.; Akiyama, T.; Manabe, K. Tetrahedron Lett. 2018, 59, 3175.
[14]
Zhou, L. X.; Shi, Y. X.; Zhu, X. Y.; Zhang, P. Tetrahedron Lett. 2019, 60, 2005.
[15]
Seo, J.; Chen, C. W.; Lee, W. Y.; Jeon, J. E.; Chen, P. L.; Chuang, S. C.; Joo, J. M. Synthesis 2021, 53, 3001.
[16]
Sun, L. L.; Liao, Z. Y.; Tang, R. Y.; Deng, C. L.; Zhang, X. G. J. Org. Chem. 2012, 77, 2850.
[16]
(b) Komiyama, M.; Tsuchiya, H.; Teramoto, M.; Yajima, N.; Kurokawa, M.; Minamizono, K.; Tsuchiya, N.; Kato, Y.; Sato, Y.; Dohi, M. Org. Process Res. Dev. 2018, 22, 1306.
[17]
Nagamochi, M.; Fang, Y. Q.; Lautens, M. Org. Lett. 2007, 9, 2955.
[18]
Lakshminarayana, B.; Chakraborty, J.; Satyanarayana, G.; Subrahmanyam, C. RSC Adv. 2018, 8, 21030.
[19]
Cheng, L. J.; Mankad, N. P. Chem. Soc. Rev. 2020, 49, 8036.
[20]
Newman, S. G.; Aureggi, V.; Bryan, C. S.; Lautens, M. Chem. Commun. 2009, 45, 5236.
[21]
Zhou, L.; Shi, Y.; Xiao, Q.; Liu, Y. Z.; Ye, F.; Zhang, Y.; Wang, J. B. Org. Lett. 2011, 13, 968.
[22]
Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2011, 13, 2395.
[23]
Liu, J. M.; Zhang, N. F.; Yue, Y. Y.; Wang, D.; Zhang, Y. L.; Zhang, X.; Zhou, K. L. RSC Adv. 2013, 3, 3865.
[24]
Liu, Y.; Wang, H.; Wan, J. P. J. Org. Chem. 2014, 79, 10599.
[25]
Gao, D.; Back, T. G. Chem.-Eur. J. 2012, 18, 14828.
[26]
Fu, R. G.; Li, Z. Org. Lett. 2018, 20, 2342.
[27]
Villuri, B. K.; Ichake, S. S.; Reddy, S. R.; Kavala, V.; Bandi, V.; Kuo, C. W.; Yao, C. F. J. Org. Chem. 2018, 83, 10241.
[28]
Zhu, X. R.; Deng, C. L. Synthesis 2021, 1842.
[29]
(a) Krause, N.; Winter, C. Chem. Rev. 2011, 111, 1994.
[29]
(b) Corma, A.; Leyva-Pérez, A.; Sabater, M. J. Chem. Rev. 2011, 111, 1657.
[30]
Fernandez-Canelas, P.; Rubio, E.; Gonzalez, J. M. Org. Lett. 2019, 21, 6566.
[31]
(a) Achar, T. K.; Maiti, S.; Jana, S.; Debabrata Maiti, D. ACS Catal. 2020, 10, 13748.
[31]
(b) Masahiro Murakami, M.; Ishida, N. Chem. Rev. 2021, 121, 264.
[32]
Hu, Z. Y.; Tong, X. F.; Liu, G. X. Org. Lett. 2016, 18, 2058.
[33]
Sun, P.; Gao, S.; Yang, C.; Guo, S. J.; Lin, A. J.; Yao, H. Q. Org. Lett. 2016, 18, 6464.
[34]
Shi, Z.; Schro?der, N.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 8092.
[35]
Trost, B. M.; Frederiksen, M. U.; Rudd, M. T. Angew. Chem., Int. Ed. 2005, 44, 6630.
[36]
Varela-Fernández, A.; González-Rodríguez, C.; Varela, J. A.; Castedo, L.; Saá, C. Org. Lett. 2009, 11, 5350.
[37]
Lee, D. H.; Kwon, K. H.; Yi, C. S. J. Am. Chem. Soc. 2012, 134, 7325.
[38]
(a) Suzuki, T. Chem. Rev. 2011, 111, 1825.
[38]
(b) Pan, S.; Shibata, T. ACS Catal. 2013, 3, 704.
[39]
Shibata, T.; Hashimoto, Y.-K.; Otsuka, M.; Tsuchikama, K.; Endo, K. Synlett 2011, 2075.
[40]
Shibata, T.; Hashimoto, Y.-k.; Otsuka, M.; Tsuchikama, K.; Endo, K. Synth. Catal. 2009, 351, 2850.
[41]
Anxionnat, B.; Pardo, D. G.; Ricci, G.; Rossen, K.; Cossy, J. Org. Lett. 2013, 15, 3876.
[42]
(a) Schneider, U.; Kobayashi, S. Acc. Chem. Res. 2012, 45, 1331.
[42]
(b) Du, G.; Wang, G.; Ma, W.; Yang, Q.; Bao, W.; Liang, X.; Zhu, L.; Lee, C.-S. Synlett 2017, 28, 1394.
[43]
Alonso-Maranon, L.; Martinez, M. M.; Sarandeses, L. A.; Gomez-Bengoa, E.; Perez Sestelo, J. I. J. Org. Chem. 2018, 83, 7970.
[44]
Radadiya, A.; Shah, A. Eur. J. Med. Chem. 2015, 97, 356.
[45]
Donohoe, T. J.; Jones, C. R.; Winter, C.In Comprehensive Organic Synthesis, 2nd ed., Vol. 8, Eds.: Knochel, P.; Molander, G. A. Elsevier, Amsterdam, 2014, pp. 794-837.
[46]
Wu, F. T.; Bai, R.X.; Gu, Y. L. Adv. Synth. Catal. 2016, 358, 2307.
[47]
Tomkinson, N. C. O.; Contiero, F.; Jones, K.; Matts, E.; Porzelle, A. Synlett 2009, 18, 3003.
[48]
Chen, W.; Zhang, Y. C.; Zhang, L.; Wang, M.; Wang, L. Chem Commun. 2011, 47, 10476.
[49]
Schevenels, F.; Markó, I. E. Org. Lett., 2012, 14, 1298.
[50]
Xie, Y. S.; Kumar, D.; Bodduri, V. D. V.; Tarani, P. S.; Zhao, B. X.; Miao, J. Y.; Jang, K.; Shin, D. S. Tetrahedron Lett. 2014, 55, 2796.
[51]
Kenchappa, R.; Bodke, Y. D.; Telkar, S.; Nagaraja, O. Russ. J. Gen. Chem. 2017, 87, 2027.
[52]
Gouthami, P.; Chavan, L. N.; Chegondi, R.; Chandrasekhar, S. J. Org. Chem. 2018, 83, 3325.
[53]
Zhang, H. W.; Ma, C. M.; Zheng, Z. W.; Sun, R. W.; Yu, X. H.; Zhao, J. H. Chem. Commun. 2018, 54, 4935.
[54]
Ranjbari, M. A.; Tavakol, H. J. Org. Chem. 2021, 86, 4756.
[55]
Wirth, T.; Singh, F. V. Synthesis 2012, 44, 1171.
[56]
Singh, F. V.; Mangaonkar, S. Synthesis 2018, 50, 4940.
[57]
Pei, T.; Chen, C.-Y.; DiMichele, L.; Davies, I. W. Org. Lett. 2010, 12, 4972.
[58]
Rao, M. L. N.; Awasthi, D. K.; Talode, J. B. Tetrahedron Lett. 2012, 53, 2662.
[59]
Wang. Z. W.; Li, Y. B.; Yan, B. Q.; Huang, M. M.; Wu, Y. J. Synlett 2015, 26, 531.
[60]
Wen, C.; Jiang, X.; Wu, K.; Luo, R. Q.; Li, Q. H. RSC Adv. 2020, 10, 19610.
[61]
Wen, C.; Wu, C.; Luo, R. Q.; Li, Q. H.; Chen, F. Synthesis 2021, 53, 3847.
[62]
Mayhugh, A. L.; Luscombe, C. K. Org. Lett. 2021, 23, 7079.
[63]
Yorimitsu, H.; Baralle, A.; Otsuka, S.; Guérin, V.; Murakami, K.; Osuka, A. Synlett 2015, 26, 327.
[64]
Yoon. H. J.; Lee, Y. M. J. Org. Chem. 2015, 80, 10244.
[65]
Yang, Q.; He, Y.; Wang, T.; Zeng, L. Y.; Zhang, Z. T. Mol. Diversity 2016, 20, 9.
Outlines

/