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 20 条

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TETRAHEDRON LETTERS, 1994, 35 (28) : 5003 - 5004
[4] AN EFFICIENT SYNTHESIS OF 3-TERT-AMINOPROPANOL DERIVATIVES BY REGIOSELECTIVE RING-OPENING OF TETRAHYDRO-1,3-OXAZINES WITH GRIGNARD-REAGENTS
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[6] ELECTROPHILIC AROMATIC REACTIVITIES VIA RING-CHAIN TAUTOMERISM OF TETRAHYDRO-1,3-OXAZINES AND OXAZOLIDINES
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[7] ELECTROPHILIC AROMATIC REACTIVITIES VIA RING CHAIN TAUTOMERISM OF TETRAHYDRO-1,3-OXAZINES AND 1,3-OXAZOLIDINES
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[8] Electrochemical Ring-Opening of Cyclopropylamides with Alcohols toward the Synthesis of 1,3-Oxazines
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ORGANIC LETTERS, 2023, 26 (14) : 2806 - 2810
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