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金催化一锅法串联构建高官能化的吡咯并[1,2-a]喹啉-1(2H)-酮

Gold-catalyzed one-pot cascade construction of highly functionalized pyrrolo[1,2-a]quinolin-1(2H)-ones.

作者信息

Zhou Yu, Feng Enguang, Liu Guannan, Ye Deju, Li Jian, Jiang Hualiang, Liu Hong

机构信息

The Center for Drug Discovery and Design, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China.

出版信息

J Org Chem. 2009 Oct 2;74(19):7344-8. doi: 10.1021/jo901418m.

Abstract

An efficient protocol was developed for the synthesis of fused heterocyclic multiring compounds pyrrolo[1,2-a]quinolin-1(2H)-ones via a AuBr(3)/AgSbF(6)-catalyzed cascade transformation. Significantly, the strategy affords a straightforward and efficient approach to construction of tricyclic lactam molecular architectures in which two new C-C bonds and one new C-N bond are formed in a one-pot synthetic operation from simple starting materials. Moreover, a broad spectrum of substrates can participate in the process effectively to produce the desired products in good yields and with excellent regio- and chemoselectivities.

摘要

通过AuBr(3)/AgSbF(6)催化的串联转化,开发了一种高效的合成稠合杂环多环化合物吡咯并[1,2-a]喹啉-1(2H)-酮的方法。值得注意的是,该策略提供了一种直接有效的方法来构建三环内酰胺分子结构,其中从简单的起始原料通过一锅法合成操作形成了两个新的C-C键和一个新的C-N键。此外,多种底物可以有效地参与该过程,以良好的产率和优异的区域和化学选择性生成所需产物。

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