ISOTHIAZOLES .5. CYCLOADDITION REACTION OF NITRILE OXIDES TO 3-DIETHYLAMINO-4-(4-METHOXYPHENYL)-ISOTHIAZOLE 1,1-DIOXIDE - AN ENTRY TO 5-ACYL-ISOTHIAZOLE 1,1-DIOXIDE AND 5-CYANO-ISOTHIAZOLE 1,1-DIOXIDE DERIVATIVES

被引：12

作者：

CLERICI, F

FERRARIS, F

GELMI, ML

机构：

[1] Istituto di Chimica Organica, Facoltà di Farmacia, I-20133 Milano

来源：

TETRAHEDRON | 1995年 / 51卷 / 45期

关键词：

D O I：

10.1016/0040-4020(95)00779-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitrile oxides 2 reacted with 3-diethylamino-4-(4-methoxyphenyl)-isothiazole 1,1-dioxide (1) affording through a highly regioselective 1,3-dipolar cycloaddition reaction isothiazolo[5,4-d]isoxazoline 4,4-dioxides 3. Reduction of 3 afforded a mixture of the E and Z forms of the corresponding 5-(amino-arylmethylene)-dihydro-isothiazole 1,1-dioxides 4/5 which were transformed into 5-acyl-dihydro-isothiazole 1,1-dioxides 6 and the corresponding dehydrated products 7. Compound 3 f was easily transformed into 5-cyanoisothiazole 1,1-dioxide 11.

引用

收藏

页码：12351 / 12362

页数：12

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