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

Articles

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   

  1. 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   

  1. 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).

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