Russian Journal of Organic Chemistry, volume 55, issue 3, pages 402-405
Reaction of Acylpyruvic Acids and Their Esters with N-(2-Aminophenyl)acetamide
Publication type: Journal Article
Publication date: 2019-03-01
Journal:
Russian Journal of Organic Chemistry
Quartile SCImago
Q4
Quartile WOS
Q4
Impact factor: 0.8
ISSN: 10704280, 16083393
Organic Chemistry
Abstract
Acylpyruvic acids and their esters regioselectively reacted with N-(2-aminophenyl)acetamide to give acyclic enamines, substituted (Z)-2-[(2-acetamidophenyl)amino]-4-oxobut-2-enoates, whose structure was confirmed by X-ray analysis. These compounds were formed as a result of condensation involving the primary amino group of N-(2-aminophenyl)acetamide at the most electrophilic C2=O carbonyl group of acylpyruvic acid or its ester. The obtained enamines underwent thermal heterocyclization to (Z)-3-(2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-ones having no substituent on the N1 atom rather than expected (Z)-1-acetyl-3-(2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-ones. The heterocyclization involves intramolecular exchange between the amide and carboxylic acid (ester) fragments. The described transformations occur under mild conditions, require no catalyst or other additives, and therefore conform to the “green chemistry” principles. The products may be interesting from the viewpoints of medicinal chemistry, pharmacology, and fine organic synthesis.
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Stepanova E. E., Dmitriev M. V., Maslivets A. N. Reaction of Acylpyruvic Acids and Their Esters with N-(2-Aminophenyl)acetamide // Russian Journal of Organic Chemistry. 2019. Vol. 55. No. 3. pp. 402-405.
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Stepanova E. E., Dmitriev M. V., Maslivets A. N. Reaction of Acylpyruvic Acids and Their Esters with N-(2-Aminophenyl)acetamide // Russian Journal of Organic Chemistry. 2019. Vol. 55. No. 3. pp. 402-405.
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TY - JOUR
DO - 10.1134/S1070428019030254
UR - https://doi.org/10.1134%2FS1070428019030254
TI - Reaction of Acylpyruvic Acids and Their Esters with N-(2-Aminophenyl)acetamide
T2 - Russian Journal of Organic Chemistry
AU - Stepanova, E E
AU - Dmitriev, M V
AU - Maslivets, A N
PY - 2019
DA - 2019/03/01 00:00:00
PB - Pleiades Publishing
SP - 402-405
IS - 3
VL - 55
SN - 1070-4280
SN - 1608-3393
ER -
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BibTex
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@article{2019_Stepanova,
author = {E E Stepanova and M V Dmitriev and A N Maslivets},
title = {Reaction of Acylpyruvic Acids and Their Esters with N-(2-Aminophenyl)acetamide},
journal = {Russian Journal of Organic Chemistry},
year = {2019},
volume = {55},
publisher = {Pleiades Publishing},
month = {mar},
url = {https://doi.org/10.1134%2FS1070428019030254},
number = {3},
pages = {402--405},
doi = {10.1134/S1070428019030254}
}
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MLA
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Stepanova, E. E., et al. “Reaction of Acylpyruvic Acids and Their Esters with N-(2-Aminophenyl)acetamide.” Russian Journal of Organic Chemistry, vol. 55, no. 3, Mar. 2019, pp. 402-405. https://doi.org/10.1134%2FS1070428019030254.