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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

Meng Li, Jia Zheng, Weigao Hu, Chunsheng Li, Jianxiao Li, Songjia Fang, Huanfeng Jiang, Wanqing Wu*

*State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, China, Email: cewuwqscut.edu.cn

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

DOI: 10.1021/acs.orglett.8b03165 (free Supporting Information)


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Abstract

A palladium-catalyzed annulation of N-acyl-o-alkynylanilines with isocyanides provides functionalized 2-aminoquinolines with high atom economy via an unconventional 6-endo-dig cyclization process. Further investigations of the mechanism revealed that an intramolecular acyl migration of the N-protecting groups is involved.

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deprotection



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

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


Key Words

quinolines


ID: J54-Y2018