RING-OPENING OF ISOXAZOLIDINE NUCLEUS - COMPETITIVE FORMATION OF ALPHA,BETA-ENONES AND TETRAHYDRO-1,3-OXAZINES

被引：24

作者：

CASUSCELLI, F

CHIACCHIO, U

RESCIFINA, A

ROMEO, R

ROMEO, G

TOMMASINI, S

UCCELLA, N

机构：

[1] UNIV CATANIA,DIPARTIMENTO SCI CHIM,I-95125 CATANIA,ITALY

[2] UNIV CALABRIA,DIPARTIMENTO CHIM,I-87036 ARCAVACATA,ITALY

来源：

TETRAHEDRON | 1995年 / 51卷 / 10期

关键词：

D O I：

10.1016/0040-4020(95)00030-C

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of isoxazolidine derivatives with methyl iodide, followed by simple heating with aqueous NaOH, gives rise to a competitive formation of alpha,beta-enones and tetahydro-1,3-oxazines. The ring-opening process is controlled by the stereochemistry of H-5 which represents the driving factor of two competitive reaction routes.

引用

页码：2979 / 2990

页数：12

共 22 条

[1] CARRUTHERS V, 1990, TETRAHEDRON ORGANIC, V8, P269
[2] RING-OPENING OF SUBSTITUTED ISOXAZOLIDINES - ONE-POT SYNTHESIS OF INDENES
CASUSCELLI, F
CHIACCHIO, U
LIGUORI, A
ROMEO, G
SINDONA, G
UCCELLA, N
[J]. TETRAHEDRON, 1993, 49 (23) : 5147 - 5152
[3] RING-OPENING OF ISOXAZOLIDINE SYSTEM - HOMOLOGATION OF 3-ARYL INTO 3-STYRYL NITRONES VIA INTERMEDIATE 5-HYDROXY-ISOXAZOLIDINES
CHIACCHIO, U
LIGUORI, A
ROMEO, G
SINDONA, G
UCCELLA, N
[J]. TETRAHEDRON, 1992, 48 (43) : 9473 - 9482
[4] CHIACCHIO U, 1993, HETEROCYCLES, V36, P2209
[5] NOVEL-APPROACH TO THE RING-OPENING OF 4-ISOXAZOLINES - ONE-POT SYNTHESIS OF ALPHA,BETA-ENONES
CHIACCHIO, U
LIGUORI, A
RESCIFINA, A
ROMEO, G
ROSSANO, F
SINDONA, G
UCCELLA, N
[J]. TETRAHEDRON, 1992, 48 (01) : 123 - 132
[6] RING-OPENING OF ISOXAZOLIDINE NUCLEUS BY TRIMETHYL PHOSPHATE TREATMENT - FORMATION OF TERTIARY ALLYLIC ALCOHOLS VIA INTERMEDIATE 1,3-OXAZINIUM SALTS
CHIACCHIO, U
LIGUORI, A
ROMEO, G
SINDONA, G
UCCELLA, N
[J]. HETEROCYCLES, 1993, 36 (04) : 799 - 817
[7] STEREOSELECTIVE CONTROL IN 1,3-DIPOLAR CYCLOADDITION OF NITRONES TO SUBSTITUTED STYRENES
CHIACCHIO, U
CASUSCELLI, F
CORSARO, A
RESCIFINA, A
ROMEO, G
UCCELLA, N
[J]. TETRAHEDRON, 1994, 50 (22) : 6671 - 6680
[8] STEREOSELECTIVE SYNTHESIS OF FUSED GAMMA-LACTAMS BY INTRAMOLECULAR NITRONE CYCLOADDITION
CHIACCHIO, U
BUEMI, G
CASUSCELLI, F
PROCOPIO, A
RESCIFINA, A
ROMEO, R
[J]. TETRAHEDRON, 1994, 50 (18) : 5503 - 5514
[9] Confalone P. N., 1988, ORG REACTIONS, V36, P1
[10] DeShong P., 1988, ADV CYCLOADDITION, V1, P87

← 1 2 3 →