N-Alkylation of Imidazoles with Dialkyl and Alkylene Carbonates

• Published in: Russian journal of organic chemistry Vol. 56; no. 12; pp. 2079 - 2086
• Main Authors: Gabov, I. S., Khamidullina, L. A., Puzyrev, I. S., Ezhikova, M. A., Kodess, M. I., Pestov, A. V.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-12-2020; Springer Nature B.V
• Subjects: Alkylation; Carbonates; Chemistry; Chemistry and Materials Science; Ethylene; Imidazole; Organic Chemistry; Quantum chemistry; alkylation; dialkyl carbonates; imidazoles; alkylene carbonates
• ISSN: 1070-4280; 1608-3393
• DOI: 10.1134/S1070428020120052

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.