STUDIES ON ORGANOSILICON CHEMISTRY .118. SYNTHESIS AND REACTIONS OF METHYL (TRIMETHYLSILYLMETHYL)-ACETYLENECARBOXYLATE - A GENERAL-METHOD FOR THE GENERATION OF DI-EXO-METHYLENEISOXAZOLINES AND NOVEL ACCESS TO FUSED ISOXAZOLES

被引:33
作者
HOJO, M [1 ]
TOMITA, K [1 ]
HOSOMI, A [1 ]
机构
[1] UNIV TSUKUBA,DEPT CHEM,TSUKUBA,IBARAKI 305,JAPAN
关键词
METHYL (TRIMETHYLSILYLMETHYL)ACETYLENECARBOXYLATE, 1,3-DIPOLAR CYCLOADDITION; 1,4-ELIMINATION; DI-EXO-METHYLENEISOXAZOLINE; DIELS-ALDER REACTION; FUSED ISOXAZOLE;
D O I
10.1016/0040-4039(93)85108-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methyl (trimethylsilylmethyl)acetylenecarboxylate, which is a common key compound in preparation of precursors for di-exo-methylene derivatives of isoxazolines, reacts with nitrile oxides to yield cycloadducts, isoxazoles. Reduction and acetylation of cycloadducts leading to 4-acetoxymethyl-5-(trimethylsilylmethyl)isoxazoles followed by fluoride ion-promoted 1,4-elimination reaction in the presence of dienophiles gave fused isoxazoles.
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页码:485 / 488
页数:4
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