Palladium-Catalyzed Intermolecular Aerobic Oxidative Cyclization of 2-Ethynylanilines with Isocyanides: Regioselective Synthesis of 4-Halo-2-aminoquinolines

Bifu Liu, Hanling Gao, Yue Yu, Wanqing Wu and Huanfeng Jiang*

*School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510640, PR China, Email: jianghfscut.edu.cn

B. Liu, H. Gao, Y. Yu, W. Wu, H. Jiang, J. Org. Chem., 2013, 78, 10319-10328.

DOI: 10.1021/jo401707j

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Abstract

A robust and regioselective palladium-catalyzed intermolecular aerobic oxidative cyclization of 2-ethynylanilines with isocyanides enables the synthesis of 4-halo-2-aminoquinolines with good yields and broad substrates scope. Furthermore, this process can be easily extended to synthesis of various 6H-indolo[2,3-b]quinolines via an intramolecular Buchwald-Hartwig cross-coupling reaction in a two-step one-pot manner.

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Palladium-Catalyzed Cyclization of N-Acyl-o-alkynylanilines with Isocyanides Involving a 1,3-Acyl Migration: Rapid Access to Functionalized 2-Aminoquinolines

M. Li, J. Zheng, W. Hu, C. Li, J. Li, S. Fang, H. Jiang, W. Wu, Org. Lett., 2018, 20, 7245-7248.

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Key Words

quinolines, oxygen

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ID: J42-Y2013