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Copper(II)-Catalyzed Aerobic Oxidative Desulfitative 6π Electrocyclization: Efficient Synthesis of Diverse 4-Aminoquinolines.
- Source :
-
Advanced Synthesis & Catalysis . Jul2017, Vol. 359 Issue 14, p2457-2470. 14p. - Publication Year :
- 2017
-
Abstract
- 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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 16154150
- Volume :
- 359
- Issue :
- 14
- Database :
- Academic Search Index
- Journal :
- Advanced Synthesis & Catalysis
- Publication Type :
- Academic Journal
- Accession number :
- 124150868
- Full Text :
- https://doi.org/10.1002/adsc.201700410