REACTION OF BETA-NITROENONES WITH THIOPHENOL - SYNTHESIS OF 5-HYDROXY-4-(PHENYLTHIO)-2-ISOXAZOLINE 2-OXIDES

被引：11
作者：
SCHNEIDER, R
GERARDIN, P
LOUBINOUX, B
RIHS, G
机构：
[1] UNIV HENRI POINCARE,LERMAB,CHIM ORGAN LAB 4,F-54506 VANDOEUVRE NANCY,FRANCE
[2] CIBA GEIGY AG,CH-4002 BASEL,SWITZERLAND
来源：
TETRAHEDRON | 1995年 / 51卷 / 17期
关键词：
D O I：
10.1016/0040-4020(95)98697-G
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new synthesis of 2-isoxazoline 2-oxides starting from unsaturated nitro compounds is described. A facile and convenient preparation of beta-alkyl substituted beta-nitroenones and their conversion to beta-nitrosulfides are recorded. Treatment of these compounds with potassium tea-butoxide at -78 degrees C followed by immediate quenching with acetic acid provides access to 5-hydroxy-4-(phenylthio)-2-isoxazoline 2-oxides via intramolecular addition of the nitronate anion to the carbonyl group.
引用
收藏
页码：4997 / 5010
页数：14
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