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Regioselective synthesis of 3-benzazepinones and unexpected 5-bromo-3-benzazepinones. 2010
Lei Zhang, and
Deju Ye, and
Yu Zhou, and
Guannan Liu, and
Enguang Feng, and
Hualiang Jiang, and
Hong Liu
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China.
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.
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