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Regioselective Synthesis of 3-Benzazepinones and Unexpected 5-Bromo-3-benzazepinones

  作者 ZHANG LEI; YE DEJU; ZHOU YU; LIU GUANNAN; FENG ENGUANG; JIANG HUALIANG; LIU HONG  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-11;  页码  3671-3677  
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[摘要]A regioselective hydroamidation of 2-(1-alkynyl)phenylacetamides with Au(PPh3)Cl/AgSbF6 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 AuBr3 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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