Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines

被引：29

作者：

Kontokosta, Dimitra ^{[1
]}

Mueller, Daniel S. ^{[1
]}

Mo, Dong-Liang ^{[1
]}

Pace, Wiktoria H. ^{[1
]}

Simpson, Rachel A. ^{[1
]}

Anderson, Laura L. ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

Beilstein Journal of Organic Chemistry | 2015年 / 11卷

基金：

美国国家科学基金会;

关键词：

Chan-Lam; copper; nitrone; oxygen transfer; pyridine; ONE-POT SYNTHESIS; ALKENYL BORONIC ACIDS; SUBSTITUTED PYRIDINES; COUPLING REACTIONS; ALPHA; BETA-UNSATURATED KETOXIMES; OXIME ESTERS; DERIVATIVES; ALKYNES; HETEROCYCLES; REAGENTS;

D O I：

10.3762/bjoc.11.226

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Chan-Lam reaction has been used to prepare N-alkenyl-alpha,beta-unsaturated nitrones, which undergo a subsequent thermal rearrangement to the corresponding tri- and tetrasubstituted pyridines. The optimization and scope of these transformations is discussed. Initial mechanistic experiments suggest a reaction pathway involving oxygen transfer followed by cyclization.

引用

收藏

页码：2097 / 2104

页数：8

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