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


Mloston, Grzegorz; Gendek, Tomasz; Heimgartner, Heinz (2000). Reactions of 2-unsubstituted 1H-imidazole 3-oxides with heterocumulenes and dimethyl acetylenedicarboxylate. Tetrahedron, 56:5405-5412.

Abstract

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.

Abstract

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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2000
Deposited On:29 Oct 2013 10:49
Last Modified:05 Apr 2016 17:05
Publisher:Elsevier
ISSN:0040-4020
Funders:Polish State Committee for Scientific Research, Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Dr. Helmut Legerlotz-Stiftung, Universität Zürich
Publisher DOI:https://doi.org/10.1016/S0040-4020(00)00449-X

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