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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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Published in: | Russian journal of organic chemistry 2020-12, Vol.56 (12), p.2079-2086 |
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Main Authors: | , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 1070-4280 1608-3393 |
DOI: | 10.1134/S1070428020120052 |