New rearrangement of 4-isoxazoline system:: Conversion of ketones into α,β-unsaturated amides

被引：21

作者：

Chiacchio, U ^{[1
]}

Rescifina, A ^{[1
]}

Chiacchio, MA ^{[1
]}

Romeo, G ^{[1
]}

Romeo, R ^{[1
]}

机构：

[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 09期

关键词：

D O I：

10.1021/jo034135+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new rearrangement pattern of the 4-isoxazoline system is reported. The reaction, starting from 3,3-disubstituted derivatives and leading to alpha/beta-unsaturated amides, proceeds through the quaternarization of the nitrogen atom and involves the heterolytic cleavage of C-3-N bond, assisted by the formation of a relatively stable intermediate. The overall process represents a useful conversion of ketones into alpha,beta-unsaturated amides.

引用

收藏

页码：3718 / 3720

页数：3

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