Spiroheterocycles via Regioselective Cycloaddition Reactions of Nitrile Oxides with 5-Methylene-1H-pyrrol-2(5H)-ones

被引：20

作者：

Beattie, Nicola J. ^{[1
]}

Francis, Craig L. ^{[1
]}

Liepa, Andris J. ^{[1
]}

Savage, G. Paul ^{[1
]}

机构：

[1] CSIRO Mol & Hlth Technol, Clayton, Vic 3169, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2010年 / 63卷 / 03期

关键词：

Chlorine compounds - Cyanides - Nitrogen oxides;

D O I：

10.1071/CH09479

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Substituted 5-methylene-1H-pyrrol-2(5H)-ones underwent a 1,3-dipolar cycloaddition reaction with nitrile oxides to give the corresponding spiro heterocycles. Critical to this reaction was the development of a biphasic system for base-induced dehydrohalogenation of hydroximoyl chlorides, to give nitrile oxides, in the presence of a base-sensitive dipolarophile. A substituted N-tolyl 5-methylene-1H-pyrrol-2(5H)-one exhibited atropisomerism, which in turn led to a 4:1 facial selectivity during cycloaddition.

引用

页码：445 / 451

页数：7

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