综述与进展

基于成环策略构建苯并呋喃的合成研究

  • 靳瑞文 ,
  • 王连杰 ,
  • 宋跃 ,
  • 刘小培 ,
  • 王俊伟 ,
  • 李中贤
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  • 河南省科学院高新技术研究中心 河南省精细化工重点实验室 郑州 450002

收稿日期: 2023-12-27

  修回日期: 2024-03-22

  网络出版日期: 2024-04-10

基金资助

河南省科技攻关项目(222102230082); 河南省科学院基本科研业务费(220602088); 河南省科学院重大科研(220102002)

Research Progress on the Synthesis of Benzofuran Based on Cyclization Strategy

  • Ruiwen Jin ,
  • Lianjie Wang ,
  • Yue Song ,
  • Xiaopei Liu ,
  • Junwei Wang ,
  • Zhongxian Li
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  • Henan Key Laboratory of Fine Chemicals, High & New Technology Research Center, Henan Academy of Sciences, Zhengzhou 450002

Received date: 2023-12-27

  Revised date: 2024-03-22

  Online published: 2024-04-10

Supported by

Key Scientific and Technological Project of Henan Province(222102230082); Fundamental Research Funds of Henan Academy of Sciences(220602088); Major Scientific Research Funds of Henan Academy of Sciences(220102002)

摘要

苯并呋喃是一种重要的结构成分, 存在于各种天然产品、农用化学品和药物中, 一直以来受到广大化学家的广泛关注. 近年来, 通过分子内和分子间环化合成苯并呋喃衍生物的报道不胜枚举, 主要有金属催化反应合成、电催化反应合成、光催化反应合成以及其他的合成方法, 并且对其反应机理进行了详细的研究, 重点针对环化合成苯并呋喃衍生物进行了详细且系统的总结.

本文引用格式

靳瑞文 , 王连杰 , 宋跃 , 刘小培 , 王俊伟 , 李中贤 . 基于成环策略构建苯并呋喃的合成研究[J]. 有机化学, 2024 , 44(9) : 2742 -2759 . DOI: 10.6023/cjoc202312027

Abstract

Benzofuran is an essential structural component found in a wide range of natural products, agrochemicals and drugs, possessing a range of biological activities. In recent years, there have been numerous reports of successful syntheses of benzofuran derivatives via intra- and inter-molecular cyclizations using diverse catalysts. This review gives an exhaustive and methodical survey of the procedures for making benzofurans.

参考文献

[1]
(a) Pacher, T.; Seger, C.; Engelmeier, D. J. Nat. Prod. 2002, 65, 820.
[1]
(b) Kao, C. L.; Chern, J. W. Tetrahedron 2001, 42, 1111.
[1]
(c) Akgul, K. K.; Anil, H. Phytochemistry 2003, 63, 939.
[1]
(d) Pu, W.; Wang, F.; Wang, C. Chin. J. Org. Chem. 2019, 39, 1277 (in Chinese).
[1]
(蒲文臣, 王飞, 王淳, 有机化学, 2019, 39, 1277.)
[1]
(e) Oschmann, M.; Holm, L. J.; Pourghasemi-Lati, M.; Verho, O. Molecules 2020, 25, 361.
[2]
(a) Zhu, J.; Tian, J. M.; Chen, Y. Y.; Hu, X. J.; Han, X.; Chen, W. C.; Yang, Z. K.; Bao, X. Z.; Ye, X. Y.; Chen, H.; Zhang, F. M.; Wang, H.; Tu, Y. Q. J. Org. Chem. 2023, 88, 14670.
[2]
(b) Khuntia, R.; Mahapatra, S. K.; Roy, L.; Pan, S. C. Chem. Sci. 2023, 14, 10768.
[2]
(c) Cabrera-Pardo1, J. R.; Fuentealba, J.; Gavilá, J.; Cajas, D.; Becerra, J.; Napiórkowska, M. Front. Pharmacol. 2020. 10. 1679.
[3]
(a) Pieters, L.; Van, D. S.; Gao, M. J. Med. Chem. 1999, 42, 5475.
[3]
(b) Pauletti, P. M.; Araujo, A. R.; Young, M. C. Phytochemistry 2000, 55, 597.
[3]
((c) Zhao, Y.; Liu, W.; Sun, X.; Lin, G. Chin. J. Org. Chem. 2012, 32, 1919 (in Chinese).
[3]
(赵云辉, 刘文杰, 孙兴文, 林国强, 有机化学, 2019, 39, 456.)
[4]
(a) Joule, A.; Smit, G. F. Heterocyclic Chemistry, 3rd ed., London, CRC Press, 1995, p. 536.
[4]
(b) Tan, Y. X.; Yang, Y.; Zhang, T. Fitoterapia 2010, 87, 742.
[4]
(c) Carey, F. A.; Sundberg, R. A. Advanced Organic Chemistry, Science Publishing Company, New York, 2007, pp. 759-762.
[5]
Nakamura, I.; Mizushima, Y.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 15022.
[6]
Kumar, M. P.; Liu, R. S. J. Org. Chem. 2006, 71, 4951.
[7]
Varela-Fernández, A.; González-Rodríguez, C.; Varela, J. A. Org. Lett. 2009, 11, 5350.
[8]
Jumbam, N. D.; Yedwa, M.; Masamba, W. Bull. Chem. Soc. Ethiop. 2011, 25, 157.
[9]
Li, H.; Liu, G. J. Org. Chem. 2014, 79, 509.
[10]
Oonishi, Y.; Gomez-Suarez, A.; Martin, A. R. Chem. Eur. J. 2014, 20, 13507.
[11]
Zhu, H. L.; Zhou, Q. Q.; Liu, N. Xing, J. H.; Yao, W. J.; Dou, X. W. Adv. Synth. Catal. 2022, 364, 1162.
[12]
Guilarte, V.; Castroviejo, M. P.; álvarez, Beilstein, E. J. Org. Chem. 2011, 7, 1255.
[13]
Kuram, M. R.; Bhanuchandra, M.; Sahoo, A. K. Angew. Chem., Int. Ed. 2013, 52, 4607.
[14]
Agasti, S.; Sharma, U.; Naveen, T.; Maiti, D. Chem. Commun. 2015, 51, 5375.
[15]
Al-Zoubi, R. M.; Al-Jammal, W. K.; Ferguson, M. J. RSC Adv. 2021, 11, 30069.
[16]
Reddy, R. J.; Sharadha, N.; Krishna, G. R. J. Org. Chem. 2023, 88, 8889.
[17]
Ghosh, S.; Das, J. Tetrahedron Lett. 2011, 52, 1112.
[18]
Ghosh, S.; Das, J.; Saikh. F. Tetrahedron Lett. 2012, 53, 5883.
[19]
Protti, S.; Fagnoni, M.; Albini, A. J. Org. Chem. 2012, 77, 6473.
[20]
Zhang, L.; Si, X.; Rominger, F.; Hashmi, A. S. K. J. Am. Chem. Soc. 2020, 142, 10485.
[21]
Zhu, Y.; He, Y. Q.; Tian, W. F.; Wang, M.; Zhou, Z. Z.; Song, X. R.; Ding, H. X.; Xiao, Q. Adv. Synth. Catal. 2021, 363, 3372.
[22]
Zhao, J.; Nguyen, S. C.; Ye, R.; Ye, B.; Weller, H.; Somorjai, G. A.; Alivisatos, A. P.; Toste, F. D. ACS Cent. Sci. 2017, 3, 482.
[23]
Fakhari, A. R.; Ahmar, H. Synth. Commun. 2011, 41, 561.
[24]
Siddiqui, I. R.; Waseem, M. A.; Shamim, S. Tetrahedron Lett. 2013, 54, 4154.
[25]
Warner, A. J.; Churn, A.; McGough, J. S. Angew. Chem., Int. Ed. 2016, 56, 354.
[26]
Ma, W.; Huang, J.; Huang, X. Org. Chem. Front. 2019, 6, 493.
[27]
Mangaonkar, S. R.; Shetgaonkar, S. E.; Vernekar, A. A. ChemistrySelect 2020, 5, 107541.
[28]
Du, W. Q.; Yang, R. J.; Wu, J. W.; Xia, Z. H. Eur. J. Org. Chem. 2023, 26, e202201497.
[29]
Li, Y. K.; Tung, C. H.; Xu, Z. H. Org. Lett. 2022, 24, 5829.
[30]
Hashmi, A. S. K.; Yang, W.; Rominger, F. Angew. Chem., Int. Ed. 2011, 50, 5762.
[31]
Oschmann, M.; Holm, L. J.; Lati, M. P. Molecules 2020, 25, 361.
[32]
Cabrera-Pardo, J. R.; Fuentealba, J.; Gavilán, J. Front. Pharmacol. 2019, 10, 1679.
[33]
Kumar, A.; Kumar, M.; Verma, A. K. J. Org. Chem. 2020, 85, 13983.
[34]
Zhang, B. B.; Li, X. M.; Li, X. X.; Yu, Z. Y.; Zhao, B. Y.; Wang, X. F.; Du, Y. F.; Zhao, K. J. Org. Chem. 2021, 86, 17274.
[35]
Geary, L. M.; Hultin, P. G. Org. Lett. 2009, 11, 5478.
[36]
Hu, Z. Y.; Dong, J. H.; Li, Z. Y.; Yuan, B.; Wei, R.Y.; Xu, X. X. Org. Lett. 2018, 20, 6750.
[37]
Abu-Hashem, A. A.; Hussein, H. A. R.; Aly, A. S.; Gouda, M. A. Synth. Commun. 2014, 44, 2285.
[38]
Heravi, M. M.; Zadsirjan, V. Heterocycl. Chem. 2015, 117, 261.
[39]
Zhang, W.; Xu, W.; Zhang, F.; Li, Y. Chin. J. Org. Chem. 2019, 39, 1277 (in Chinese).
[39]
(张文生, 许文静, 张斐, 李焱, 有机化学, 2019, 39, 1277.)
[40]
Huang, J.; Fu, R.; Jing, L.; Qin, D.; Huang, K.; Wang, W. Chin. J. Org. Chem. 2019, 39, 456 (in Chinese).
[40]
(黄锦, 付荣辉, 敬林海, 秦大斌, 黄昆, 汪伟, 有机化学, 2019, 39, 456.)
[41]
Naveen, T. Tetrahedron 2021, 84, 132025.
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