title: Regioselective synthesis of 3-benzazepinones and unexpected 5-bromo-3-benzazepinones.
abstract: A regioselective hydroamidation of 2-(1-alkynyl)phenylacetamides with Au(PPh(3))Cl/AgSbF(6) as the catalyst proceeded by a 7-endo-dig pathway to afford 3-benzazepinones. This method accommodates a broad range of alkyl and aryl alkynyl substitutes in moderate to high yields (63-91%). Moreover, unexpectedly, we also discovered a gold-mediated transformation from 2-(1-alkynyl)phenylacetamides to 5-bromo-3-benzazepinones, and AuBr(3) was found to not only play an activation role but also act as a reactant in the reaction for the first time.
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China.
authors.forename: Lei
authors.initials: L
authors.lastname: Zhang
authors.forename: Deju
authors.initials: D
authors.lastname: Ye
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhou
authors.forename: Guannan
authors.initials: G
authors.lastname: Liu
authors.forename: Enguang
authors.initials: E
authors.lastname: Feng
authors.forename: Hualiang
authors.initials: H
authors.lastname: Jiang
authors.forename: Hong
authors.initials: H
authors.lastname: Liu
mesh_terms: D000081:Acetamides / Q000737:chemistry; D001552:Benzazepines / Q000138:chemical synthesis*; D006046:Gold / Q000737:chemistry; D054879:Halogenation; D007659:Ketones / Q000138:chemical synthesis; D008722:Methods
chemical_list: D000081:Acetamides; D001552:Benzazepines; D007659:Ketones; D006046:Gold