区域选择性合成 3-苯并氮杂䓬酮和意外的 5-溴-3-苯并氮杂䓬酮。

Regioselective synthesis of 3-benzazepinones and unexpected 5-bromo-3-benzazepinones.

机构信息

State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China.

出版信息

J Org Chem. 2010 Jun 4;75(11):3671-7. doi: 10.1021/jo100378u.

DOI:10.1021/jo100378u

PMID:20443617

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.

摘要

金(PPh(3))氯/AgSbF(6)催化 2-(1-炔基)苯乙酰胺的区域选择性氢氨化反应，通过 7-endo-dig 途径生成 3-苯并氮杂卓酮。该方法可容纳各种烷基和芳基炔基取代基，产率中等至高产率（63-91%）。此外，出乎意料的是，我们还发现了一种由 2-(1-炔基)苯乙酰胺向 5-溴-3-苯并氮杂卓酮的金介导转化，并且首次发现 AuBr(3)不仅起活化作用，而且还作为反应物参与反应。