State Key Laboratory of Coordination Chemistry, Institute of Chemical Biology and Drug Innovation, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, PR China.
Org Lett. 2011 Aug 19;13(16):4208-11. doi: 10.1021/ol201542h. Epub 2011 Jul 18.
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.
开发了一种有效的合成方法，通过铜（II）促进的顺序 6-endo-二氯环化和氧化芳构化，从 N-丙炔基氨基醌组装 1-氮杂蒽醌。该方法可扩展至制备氯化生物碱，如 cleistophine 和 sampangine。提出了一种可能的机制，涉及通过区域选择性亲电活化引发的碳-碳键形成以及通过还原消除形成碳-氯键。
