Reactions of 2-unsubstituted 1H-imidazole 3-oxides with heterocumulenes and dimethyl acetylenedicarboxylate

被引：26

作者：

Mloston, G

Gendek, T

Heimgartner, H

机构：

[1] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland

[2] Univ Lodz, Sect Heteroorgan Cpds, PL-90136 Lodz, Poland

来源：

TETRAHEDRON | 2000年 / 56卷 / 30期

关键词：

imidazole N-oxides; isocyanates; isothiocyanates; acetylenedicarboxylate; 3+2] cycloadducts;

D O I：

10.1016/S0040-4020(00)00449-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of 2-unsubstituted 1H-imidazole 3-oxides with isocyanates, isothiocyanates, and dimethyl acetylenedicarboxylate led to the formation of 2-functionalized imidazole derivatives. Stepwise reaction mechanisms via zwitterionic intermediates are proposed. The intermediate [3+2] cycloadducts stabilize via extrusion of COX or ring opening. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：5405 / 5412

页数：8

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