CuCl<sub>2</sub>-Promoted 6-<i>endo-dig</i> Chlorocyclization and Oxidative Aromatization Cascade: Efficient Construction of 1-Azaanthraquinones from <i>N</i>-Propargylaminoquinones
Na Fei (2175680)Hao Yin (381910)Shaozhong Wang (1505020)Huaqin Wang (724353)Zhu-Jun Yao (297585)
Abstract
An efficient synthetic methodology was developed to assemble 1-azaanthraquinones from <i>N</i>-propargylaminoquinones by copper(II)-promoted sequential 6-<i>endo-dig</i> 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.
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