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