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N-Alkylation of Imidazoles with Dialkyl and Alkylene Carbonates

The reactions of imidazoles with a series of dialkyl and alkylene carbonates afforded the corresponding N -alkyl- and N -(hydroxyalkyl)imidazoles with high yields. The reactivity of dialkyl carbonates decreases in the series dimethyl > diethyl > dibutyl carbonate. Ethylene carbonate is a more...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2020-12, Vol.56 (12), p.2079-2086
Main Authors: Gabov, I. S., Khamidullina, L. A., Puzyrev, I. S., Ezhikova, M. A., Kodess, M. I., Pestov, A. V.
Format: Article
Language:English
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Summary:The reactions of imidazoles with a series of dialkyl and alkylene carbonates afforded the corresponding N -alkyl- and N -(hydroxyalkyl)imidazoles with high yields. The reactivity of dialkyl carbonates decreases in the series dimethyl > diethyl > dibutyl carbonate. Ethylene carbonate is a more efficient alkylating agent than trimethylene carbonate. The mechanisms of alkylation of imidazole with dimethyl carbonate and ethylene carbonate were studied by DFT quantum chemical calculations at the B3LYP/6-311++G( d , p ) level of theory.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428020120052