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Copper(II)‐Catalyzed Aerobic Oxidative Desulfitative 6π Electrocyclization: Efficient Synthesis of Diverse 4‐Aminoquinolines
Author(s) -
Shi Lou,
Pan Ling,
Li Yifei,
Liu Qun
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700410
Subject(s) - chemistry , aminoquinolines , catalysis , reagent , stoichiometry , combinatorial chemistry , oxidative phosphorylation , ketene , copper , disulfide bond , organic chemistry , medicinal chemistry , biochemistry
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.