Volume 54, Issue 2 pp. 965-978
Article

Efficient Synthesis of 9H-Pyrrolo[1,2-α]Indoles via Michael Addition–Condensation of 3-Substituted Indoles with α,β-Unsaturated Ketimines

Minmin Zhang

Minmin Zhang

Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China

University of Chinese Academy of Sciences, Beijing, 100049 China

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Lihua Liao

Lihua Liao

Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China

University of Chinese Academy of Sciences, Beijing, 100049 China

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Shuowen Yu

Shuowen Yu

Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China

University of Chinese Academy of Sciences, Beijing, 100049 China

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Yijun Liao

Yijun Liao

Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China

University of Chinese Academy of Sciences, Beijing, 100049 China

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Xiaoying Xu

Xiaoying Xu

Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China

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Weicheng Yuan

Weicheng Yuan

Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China

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Xiaomei Zhang

Corresponding Author

Xiaomei Zhang

Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China

E-mail: [email protected]Search for more papers by this author
First published: 04 May 2016
Citations: 7

Abstract

By employing copper dibromide as a catalyst, Michael addition–condensation of 3-substituted indoles with α,β-unsaturated ketimines was realized. The reactions afforded a large variety of 9H-pyrrolo[1,2-α]indoles with good yields (up to 99 %). In addition, a plausible reaction mechanism was proposed.

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