title: CuCl2-promoted 6-endo-dig chlorocyclization and oxidative aromatization cascade: efficient construction of 1-azaanthraquinones from N-propargylaminoquinones.
abstract: 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.
authors.affiliation: 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.
authors.forename: Na
authors.initials: N
authors.lastname: Fei
authors.forename: Hao
authors.initials: H
authors.lastname: Yin
authors.forename: Shaozhong
authors.initials: S
authors.lastname: Wang
authors.forename: Huaqin
authors.initials: H
authors.lastname: Wang
authors.forename: Zhu-Jun
authors.initials: ZJ
authors.lastname: Yao
mesh_terms: D000634:Aminoquinolines / Q000737:chemistry*; D000880:Anthraquinones / Q000138:chemical synthesis*; D001372:Aza Compounds / Q000138:chemical synthesis*; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011407:Propane / Q000737:chemistry*
chemical_list: D000634:Aminoquinolines; D000880:Anthraquinones; D001372:Aza Compounds; D003300:Copper; C029892:cupric chloride; D011407:Propane