RING-OPENING OF ISOXAZOLIDINE SYSTEM - HOMOLOGATION OF 3-ARYL INTO 3-STYRYL NITRONES VIA INTERMEDIATE 5-HYDROXY-ISOXAZOLIDINES

被引:7
作者
CHIACCHIO, U
LIGUORI, A
ROMEO, G
SINDONA, G
UCCELLA, N
机构
[1] UNIV RENDE,DIPARTIMENTO CHIM,I-87036 RENDE,ITALY
[2] UNIV MESSINA,DIPARTIMENTO FARMACO CHIM,I-98168 MESSINA,ITALY
关键词
D O I
10.1016/S0040-4020(01)88315-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
High yield conversion of 3-aryl-5-ethoxy-isoxazolidines into 3-styryl nitrones has been achieved by 1,5 h refluxing in aq. H2SO4 or catalytic p-toluensulfonic acid/ethanol media. The rearrangement pathway is interpretable on the basis of the ring-opening process of intermediate 5-hydroxy-isoxazolidines. Formation of a masked 5-OH function has been also developed by basic or acid treatment of 5-acetoxy-isoxazolidines.
引用
收藏
页码:9473 / 9482
页数:10
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1990, APR ANN M ROY SOC CH