Cu(I)-Catalyzed Intramolecular Cyclization of Ortho-halogenated Phenylthioacetamides for the Synthesis of 2-Amino Benzo[b]thiophenes

doi:10.6023/cjoc201605030

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (10): 2419-2425.DOI: 10.6023/cjoc201605030 Previous Articles Next Articles

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Cu(I)-催化邻卤硫代苯乙酰胺的分子内环化合成2-氨基苯并噻吩

李红亮, 王正林, 邓卫平

华东理工大学药学院上海市功能性材料化学重点实验室上海 200237

收稿日期:2016-05-17 修回日期:2016-06-28 发布日期:2016-07-08
通讯作者: 邓卫平,E-mail:weiping_deng@ecust.edu.cn E-mail:weiping_deng@ecust.edu.cn
基金资助:
国家自然科学基金（No.21372074）资助项目.

Cu(I)-Catalyzed Intramolecular Cyclization of Ortho-halogenated Phenylthioacetamides for the Synthesis of 2-Amino Benzo[b]thiophenes

Li Hongliang, Wang Zhenglin, Deng Weiping

Shanghai Key Laboratory of Functional Materials Chemistry & School of Pharmacy, East China University of Science and Technology, Shanghai 200237

Received:2016-05-17 Revised:2016-06-28 Published:2016-07-08
Supported by:
Project supported by the National Natural Science Foundation of China (No.21372074).

1. Cu(I)-Catalyzed Intramolecular Cyclization of Ortho-halogenated Phenylthioacetamides for the Synthesis of 2-Amino Benzo[b]thiophenes.PDF(1289KB)

Abstract

The Cu(I)-catalyzed intramolecular cyclization of ortho-halogenated phenylthioacetamides to form 2-amino ben-zo[b]thiophenes in water was studied. This method employed water instead of organic solvent, and the catalyst-loading can be as low as to 5 mol% and the yield of products is up to 98%, which overcomes the drawbacks such as harsh reaction conditions and low yields in the previous methods. In addition, the reaction can be scaled up to gram-scale and catalyst can be reused with a maintained yield of products. This reaction provided a simple and environmentally friendly protocol for the preparaion of 2-amino benzo[b]thiophene and their derivatives.

Key words: 2-amino benzo[b]thiophenes, Cu-catalyzed, water-phase, ortho-halogenated phenylthioacetamides

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Li Hongliang, Wang Zhenglin, Deng Weiping. Cu(I)-Catalyzed Intramolecular Cyclization of Ortho-halogenated Phenylthioacetamides for the Synthesis of 2-Amino Benzo[b]thiophenes[J]. Chin. J. Org. Chem., 2016, 36(10): 2419-2425.

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[1] (a) Perepichka, I. F.; Perepichka, D. F. Handbook of Thio-phene-Based Materials, Wiley-VCH Verlag, New York, 2009. (b) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893. (c) Zhang, T. Y.; O'Toole, J.; Proctor, C. S. Sulfur Reports 1999, 22, 1. (d) Guo, H. F.; Shao, H. Y.; Yang, Z. Y.; Xue, S. T.; Li, X.; Liu, Z. Y.; He, X. B.; Jiang, J. D.; Zhang, Y. Q.; Si, S. Y.; Li, Z. R. J. Med. Chem. 2010, 53, 1819. (c) Berrade, L.; Aisa, B.; Ramirez, M.; Galiano, S.; Guccione, S.; Moltzau, L. R.; Levy, F. O.; Nicoletti, F.; Battaglia, G.; Molinaro, G.; Aldana, I.; Monge, A.; Perez-Silandes, S. J. Med. Chem. 2011, 54, 3086.
[2] (a) Chonan, T.; Wakasugi, D.; Yamamoto, D.; Yashiro, M.; Oi, T.; Tanaka, H.; Ohoka-Sugita, A.; Io, F.; Koretsune, H.; Hiratate, A. Biorg. Med. Chem. 2011, 19, 1580. (b) Romagnoli, R.; Baraldi, P. G.; Carrion, M. D.; Cara, C. L.; Preti, D.; Fruttarolo, F.; Pavani, M. G.; Tabrizi, M. A.; Tolomeo, M.; Grimaudo, S. J. Med. Chem. 2007, 50, 2273. (c) Matthews, J. M. US 201001603372010[Chem. Abstr. 2010, 153, 116343]. (d) Krajewski, K.; Zhang, Y.; Parrish, D.; Deschamps, J.; Roller, P. P.; Pathak, V. K. Bioorg. Med. Chem. Lett. 2006, 16, 3034. (e) Duan, Z.; Ranjit, S.; Liu, X. Org. Lett. 2010, 12, 2430. (f) Chalmers, M. J.; Wang, Y.; Novick, S.; Sato, M.; Bryant, H. U.; Montrose-Rafizdeh, C.; Griffin, P. R.; Dodge, J. A. ACS Med. Chem. Lett. 2012, 3, 207. (g) Qin, Z.; Kastrati, I.; Chandrasena, R. E. P.; Liu, H.; Yao, P.; Petukhov, P. A.; Bolton, J. L.; Thatcher, G. R. J. Med. Chem. 2007, 50, 2682.
[3] Brower, K. R.; Amstutz, E. J. Org. Chem. 1954, 19, 411.
[4] Ablenas, F.; George, B.; Maleki, M.; Jain, R.; Hopkinson, A.; Lee-Ruff, E. Can. J. Chem. 1987, 65, 1800.
[5] Solovyev, A. Y.; Androsov, D. A.; Neckers, D. C. J. Org. Chem. 2007, 72, 3122.
[6] Hou, C.; He, Q.; Yang, C. Org. Lett. 2014, 16, 5040.
[7] Willis, M. C.; Taylor, D.; Gillmore, A. T. Tetrahedron 2006, 62, 11513.
[8] (a) Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett. 1978, 7, 13. (b) Li, G. Angew Chem, Int Ed. 2001, 40, 1513. (c) Suzuki, H.; Abe, H.; Osuka, A. Chem. Lett. 1980, 9, 1363. (d) Joyce, L. L.; Evindar, G.; Batey, R. A. Chem. Commun. 2004, 40, 446. (e) Qin, Y.; Peng, Q. Chin. J. Org. Chem. 2011, 31, 1169(in Chinese). (秦元成, 彭强, 有机化学, 2011, 31, 1169.) (f) Zhu, N.; Zhang, Z.; Gao, M.; Han, L.; Suo, Q.; Hong, H. Chin. J. Org. Chem. 2013, 33, 1423(in Chinese). (竺宁, 薛士徐, 高敏, 韩利民, 索全伶, 洪海龙, 有机化学, 2013, 33, 1423.)
[9] (a) Wang, Z.; Li, H.; Ge, L.; An, X.; Zhang, Z.; Luo, X.; Fossey, J. S.; Deng, W. J. Org. Chem. 2014, 79, 1156. (b) Ge, L.; Wang, Z.; An, X.; Luo, X.; Deng, W. Org. Biomol. Chem. 2014, 42, 8473. (c) Luo, X.; Ge, L.; An, X.; Jin, J.; Wang, Y.; Sun, P.; Deng, W. J. Org. Chem. 2015, 80, 4611.
[10] (a) Carril, M.; San Martin, R.; Domínguez, E.; Tellitu, I. Chem. Eur. J. 2007, 13, 5100. (b) Rout, L.; Saha, P.; Jammi, S.; Punniyamurthy, T. Eur. J. Org. Chem. 2008, 640. (c) Ke, F.; Qu, Y.; Jiang, Z.; Li, Z.; Zhou, X. Org. Lett. 2011, 13, 454. (d) Wang, F.; Chen, C.; Deng, G.; Xi, C. J. Org. Chem. 2012, 77, 4148. (e) Li, Z.; Wu, Z.; Deng, H.; Zhou, X. Chin. J. Org. Chem. 2013, 33, 760(in Chinese). (李正凯, 吴之清, 邓杭, 周向葛, 有机化学, 2013, 33, 760.) (f) Wen, L.-R.; Li, S.-L.; Zhang, J.; Li, M. Green Chem. 2015, 17, 1581. (g) Wen, L.-R.; Yuan, W.-K. Li, M. J. Org. Chem. 2015, 80, 4942.
[11] Evindar, G.; Batey, R. A. J. Org. Chem. 2006, 71, 1802.

Cu(I)-催化邻卤硫代苯乙酰胺的分子内环化合成2-氨基苯并噻吩

Cu(I)-Catalyzed Intramolecular Cyclization of Ortho-halogenated Phenylthioacetamides for the Synthesis of 2-Amino Benzo[b]thiophenes

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