有机化学 ›› 2016, Vol. 36 ›› Issue (6): 1351-1358.DOI: 10.6023/cjoc201601025 上一篇    下一篇

研究论文

Cu(OTf)2和脯氨亚磺酰胺共同催化吲哚与N-磺酰醛亚胺的Friedel-Crafts反应

刘海华, 张东华, 王夏辉, 孟卫东, 黄焰根   

  1. 东华大学化学化工与生物工程学院上海 201620
  • 收稿日期:2016-01-20 修回日期:2016-02-15 出版日期:2016-06-25 发布日期:2016-02-24
  • 通讯作者: 黄焰根 E-mail:hyg@dhu.edu.cn
  • 基金资助:

    上海市教委科研创新(No.13ZZ047)和中央高校基本科研业务费专项资金(No.2232015D3-13)资助项目.

Cu(OTf)2 and N-Sulfinylprolinamide Catalyzed Friedel-Crafts Reaction of Indoles with N-Sulfonylaldimines

Liu Haihua, Zhang Donghua, Wang Xiahui, Meng Weidong, Huang Yangen   

  1. College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620
  • Received:2016-01-20 Revised:2016-02-15 Online:2016-06-25 Published:2016-02-24
  • Supported by:

    Project supported by the Innovation Program of Shanghai Municipal Education Commission (No. 13ZZ047) and the Fundamental Research Funds for the Central Universities (No. 2232015D3-13).

3-取代吲哚甲胺衍生物因其多种生物活性而备受关注. 吲哚与N-磺酰醛亚胺的Friedel-Crafts反应是制备3-取代吲哚甲胺衍生物的主要方法, 但反应中通常会伴随大量的双吲哚甲烷化合物的生成. 应用Cu(OTf)2和脯氨亚磺酰胺共同催化吲哚与N-磺酰醛亚胺的Friedel-Crafts反应, 可以选择性地合成3-取代吲哚甲胺衍生物, 产率为65%~93%. 该方法具有底物适用性好、反应条件温和、操作简单等优点.

关键词: 亲电取代, 杂环化合物, 脯氨亚磺酰胺, 3-取代吲哚甲胺衍生物, Friedel-Crafts反应

3-Indolyl methanamine derivatives have attracted much attention due to their multiple potent bioactivities. The Friedel-Crafts reaction between indole and N-sulfonylaldimine is a major method for preparation of 3-indolyl methanamine derivatives, however, abundant bisindolyl methane will be formed during the reaction. 3-Indolylmethanamine derivatives were selectively synthesized in 65%~93% yields by the Friedel-Crafts amidoalkylation reaction of indoles and N-sulfonylaldimines utilizing Cu(OTf)2 and N-sulfinylprolinamide as catalysts. This method exhibited several features such as broad substrate applicability, mild reaction condition and simple operation.

Key words: electrophilic substitution, heterocycles, N-sulfinylprolinamide, 3-indolyl methanamine derivatives, the Friedel- Crafts amidoalkylation