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 inRussian journal of organic chemistry Vol. 54; no. 4; pp. 573 - 577
Main Authors Ivanov, D. V., Igidov, N. M., Shurov, S. N., Dmitriev, M. V., Chernov, I. N.
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 01.04.2018
Springer Nature
Springer Nature B.V
Subjects
Alcohol
Alcohols
Aromatic compounds
Carboxylates
Catalysis
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Organic Chemistry
Physical Sciences
Quantum chemistry
Reaction mechanisms
Science & Technology
DERIVATIVES
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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