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Cleavage of C-C Bonds for the Synthesis of C2-Substituted Quinolines and Indoles by Catalyst-Controlled Tandem Annulation of 2-Vinylanilines and Alkynoates

Jixiang Ni, Yong Jiang, Zhenyu An and Rulong Yan*

*State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Gansu, China, Email: yanrllzu.edu.cn

J. Ni, Y. Jiang, Z. An, R. Yan, Org. Lett., 2018, 20, 1534-1537.

DOI: 10.1021/acs.orglett.8b00260 (free Supporting Information)


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Abstract

A tandem Michael addition, C-C bond cleavage, and cyclization of 2-vinylanilines and alkynoates provides 2-substituted indoles and quinolines. Whereas C2-substituted indoles can be accessed in good yields under metal-free conditions, the simple method for the generation of the C2-substituted quinolines in moderate yields is Pd-catalyzed.

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Key Words

Indoles


ID: J54-Y2018