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CuCl2-Promoted 6-endo-dig Chlorocyclization and Oxidative Aromatization Cascade: Efficient Construction of 1-Azaanthraquinones from N-Propargylaminoquinones

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posted on 2011-08-19, 00:00 authored by Na Fei, Hao Yin, Shaozhong Wang, Huaqin Wang, Zhu-Jun Yao
An efficient synthetic methodology was developed to assemble 1-azaanthraquinones from N-propargylaminoquinones by copper(II)-promoted sequential 6-endo-dig chlorocyclization and oxidative aromatization. The approach can be extended to preprare chlorinated alkaloids such as cleistophine and sampangine. A possible mechanism involving carbon–carbon bond formation triggered by regioselective electrophilic activation and carbon–chlorine bond formation via reductive elimination was proposed.