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Ambivalent Nucleophilicity of 1,4,5-Trisubstituted Imidazole-2-thiones in Reactions with Dimethyl Acetylenedicarboxylate and Phenylisocyanate


Mloston, G; Gendek, T; Linden, A; Heimgartner, H (2008). Ambivalent Nucleophilicity of 1,4,5-Trisubstituted Imidazole-2-thiones in Reactions with Dimethyl Acetylenedicarboxylate and Phenylisocyanate. Polish Journal of Chemistry, 82(8):1561-1569.

Abstract

The 1,4,5-trisubstitued 2,3-dihydro-1H-imidazole-2-thiones 1 react with electrophilic reagents via the S- or the N(3)-atom. The reaction with dimethyl acetylenedicarboxylate in methanol at room temperature occurs by the nucleophilic addition of the S-atom to give the corresponding 2-[(1H-imidazol-2-yl)sulfanyl]fumarates 4 in high yield. On the other hand, imidazole-2-thiones 1 react with phenylisocyanate in dichloromethane at room temperature to yield 2,3-dihydro-2-thioxo-1H-imidazole-1-carboxamides 5. The structures of both types of adducts were established by X-ray crystallography.

Abstract

The 1,4,5-trisubstitued 2,3-dihydro-1H-imidazole-2-thiones 1 react with electrophilic reagents via the S- or the N(3)-atom. The reaction with dimethyl acetylenedicarboxylate in methanol at room temperature occurs by the nucleophilic addition of the S-atom to give the corresponding 2-[(1H-imidazol-2-yl)sulfanyl]fumarates 4 in high yield. On the other hand, imidazole-2-thiones 1 react with phenylisocyanate in dichloromethane at room temperature to yield 2,3-dihydro-2-thioxo-1H-imidazole-1-carboxamides 5. The structures of both types of adducts were established by X-ray crystallography.

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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:2008
Deposited On:06 Feb 2009 12:58
Last Modified:21 Nov 2017 13:55
Publisher:Polskie Towarzystwo Chemiczne
ISSN:0137-5083
Funders:Polish Ministry for Science and Higher Education, F. Hoffmann-La Roche AG, Basel
Official URL:http://ichf.edu.pl/pjch/pj-2008.htm
Related URLs:http://ichf.edu.pl/pjch/ (Publisher)

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