Isothiazoles .6. Cycloaddition of azides to isothiazole dioxides: Synthesis of thiadiazabicyclo[3.1.0]hexene derivatives and their thermal rearrangement to thiazete dioxides, 1,2,6-thiadiazine dioxides and pyrazoles.

被引：12

作者：

Clerici, F ^{[1
]}

Galletti, F ^{[1
]}

Pocar, D ^{[1
]}

Roversi, P ^{[1
]}

机构：

[1] UNIV MILAN,FAC CHIM,DIPARTIMENTO CHIM FIS & ELETTROCHIM,I-20133 MILAN,ITALY

来源：

TETRAHEDRON | 1996年 / 52卷 / 20期

关键词：

D O I：

10.1016/0040-4020(96)00336-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Diethylamino-4-(4-methoxyphenyl)-isothiazole 1,1-dioxide(1) was made to react with arylalkyl- and arylazides 2. Cycloadducts 3, which could he isolated in some cases, afforded N-arylalkyl or N-aryl-thiadiazabicyclo[3.1.0]hexene derivatives 4 through N-2-elimination. Thermal rearrangements of N-aryl- and N-beta-phenylethyl substituted compounds 4b-e, produced derivatives of 1,2-thiazete 1,1-dioxide 5, 1,2,6-thiadiazine 1,1-dioxide 6 and pyrazole 7. The reaction can be optimized to afford compounds 6 in synthetically useful yield. In the case of N-benzyl-thiadiazabicyclo[3.1.0]hexene derivative 4a the different substitution on the aziridine nitrogen produced a different reaction course, affording the thiadiazine derivative 6a and the pyrimidine derivative 8. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：7183 / 7200

页数：18

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