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
收藏
页码：445 / 451
页数：7
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