Reactions of Ethyl 2-Amino-5-(2-aryl-2-oxoethylidene)- 4-oxo-4,5-dihydrofuran-3-carboxylates and 2-Amino-5-(2-aryl- 2-oxoethylidene)-4-oxo-4,5-dihydrofuran-3-carbonitriles with Alcohols

Ethyl 2-amino-5-(2-aryl-2-oxoethylidene)-4-oxo-1 H -4,5-dihydrofuran-3-carboxylates and 2-amino- 5-(2-aryl-2-oxoethylidene)-4-oxo-1 H -4,5-dihydrofuran-3-carbonitriles reacted with alcohols in the presence of a catalytic amount of concentrated aqueous HCl to give the corresponding 5-alkoxy-2-amino-5...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2018-04, Vol.54 (4), p.573-577
Main Authors: Ivanov, D. V., Igidov, N. M., Shurov, S. N., Dmitriev, M. V., Chernov, I. N.
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Aromatic compounds
Carboxylates
Catalysis
Chemistry
Chemistry and Materials Science
Organic Chemistry
Quantum chemistry
Reaction mechanisms
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Summary:Ethyl 2-amino-5-(2-aryl-2-oxoethylidene)-4-oxo-1 H -4,5-dihydrofuran-3-carboxylates and 2-amino- 5-(2-aryl-2-oxoethylidene)-4-oxo-1 H -4,5-dihydrofuran-3-carbonitriles reacted with alcohols in the presence of a catalytic amount of concentrated aqueous HCl to give the corresponding 5-alkoxy-2-amino-5-(2-aryl-2- oxoethyl)-4-oxo-1 H -4,5-dihydrofuran-3-carboxylic acid derivatives. A probable reaction mechanism was proposed on the basis B3LYP/6-311G( d ) quantum chemical calculations.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428018040097