Advanced Synthesis and Catalysis
Advanced Synthesis and Catalysis
5 years ago

Copper(II)-Catalyzed Aerobic Oxidative Desulfitative 6π Electrocyclization: Efficient Synthesis of Diverse 4-Aminoquinolines

Copper(II)-Catalyzed Aerobic Oxidative Desulfitative 6π Electrocyclization: Efficient Synthesis of Diverse 4-Aminoquinolines
Lou Shi, Yifei Li, Ling Pan, Qun Liu
The C−C bond formation via C−S bond activation (disclosed in 2000) has received increasing attention. However, stoichiometric amounts of exogenous thiophilic reagents are generally required as thiolate scavengers. Herein, a new model for the synthesis of 4-aminoquinolines, the copper(II)-catalyzed aerobic oxidative desulfitative 6π cyclization of the readily available N-arylimino ketene N,S-acetals is described. The reaction can proceed efficiently under mild conditions without any exogeneous thiolate scavengers (due to the formation of disulfide as the by-product) to afford diverse 4-aminoquinolines, a privileged structure motif displaying antimalarial activity, with a wide range of functional groups at the C-2 to C-8 positions.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/adsc.201700410

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