Regioselective synthesis of 3-benzazepinones and unexpected 5-bromo-3-benzazepinones.
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.
Zhang
Lei
L
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China.
Ye
Deju
D
Zhou
Yu
Y
Liu
Guannan
G
Feng
Enguang
E
Jiang
Hualiang
H
Liu
Hong
H
D000081:Acetamides / Q000737:chemistry; D001552:Benzazepines / Q000138:chemical synthesis*; D006046:Gold / Q000737:chemistry; D054879:Halogenation; D007659:Ketones / Q000138:chemical synthesis; D008722:Methods
D000081:Acetamides; D001552:Benzazepines; D007659:Ketones; D006046:Gold