Russian Journal of Organic Chemistry, volume 49, issue 5, pages 719-729
Features of reactions of polyfluorinated ethyl 4-oxo-2-pnenyl-4H-chromene-3-carboxylates with N-nucleophiles
Publication type: Journal Article
Publication date: 2013-05-01
Journal:
Russian Journal of Organic Chemistry
Quartile SCImago
Q4
Quartile WOS
Q4
Impact factor: 0.8
ISSN: 10704280, 16083393
Organic Chemistry
Abstract
Ethyl 5,6,7,8-tetrafluoro-4-oxo-2-phenyl-4H-chromene-3-carboxylate in reactions with primary amines is characterized by a chromone-coumarin rearrangement affording 3-[amino(phenyl)methylene]-6,7,8-trifluoro-2H-chromene-2,4(3H)-diones, and ethyl 4-oxo-2-phenyl-5,6,7,8-tetrafluoro-4H-chromene-3-carboxylate characteristically adds the amine at the C2 site of the flavone furnishing 3-amino-3-phenyl-2-(2,3,4,5-tetrafluoro-6-hydroxybenzoyl)acrylates which depending on the substituent at the amino group are capable of intramolecular cyclization into 3-[(alkylamino)(phenyl)methylene]-5,6,7,8-tetrafluoro-2H-chromene-2,4(3H)-dione or in the case of benzylamine substituent, into ethyl 1-benzyl-5-hydroxy-4-oxo-2-phenyl-6,7,8-trifluoro-1,4-dihydroquinoline-3-carboxylate. The main process in the reaction of tri- and tetrafluoroflavones with secondary amine (1-methylpiperazine) is the nucleophilic substitution at the C7 of flavone. In the reaction with 1,2-phenylenediamine 3-[(2-aminophenyl)amino]-3-phenyl-2-(2,3,4,5-tetrafluoro-6-hydroxybenzoyl)acrylate was obtained from tetrafluoroflavone and 1H-benzimidazol-2-yl(3,4,5-trifluoro-2-hydroxyphenyl)methanone, from trifluoroflavone.
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- We do not take into account publications without a DOI.
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Shcherbakov K. V., Burgart Y. V., Saloutin V. I. Features of reactions of polyfluorinated ethyl 4-oxo-2-pnenyl-4H-chromene-3-carboxylates with N-nucleophiles // Russian Journal of Organic Chemistry. 2013. Vol. 49. No. 5. pp. 719-729.
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Shcherbakov K. V., Burgart Y. V., Saloutin V. I. Features of reactions of polyfluorinated ethyl 4-oxo-2-pnenyl-4H-chromene-3-carboxylates with N-nucleophiles // Russian Journal of Organic Chemistry. 2013. Vol. 49. No. 5. pp. 719-729.
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TY - JOUR
DO - 10.1134/s1070428013050151
UR - https://doi.org/10.1134/s1070428013050151
TI - Features of reactions of polyfluorinated ethyl 4-oxo-2-pnenyl-4H-chromene-3-carboxylates with N-nucleophiles
T2 - Russian Journal of Organic Chemistry
AU - Shcherbakov, K V
AU - Burgart, Ya. V.
AU - Saloutin, V. I.
PY - 2013
DA - 2013/05/01 00:00:00
PB - Pleiades Publishing
SP - 719-729
IS - 5
VL - 49
SN - 1070-4280
SN - 1608-3393
ER -
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@article{2013_Shcherbakov,
author = {K V Shcherbakov and Ya. V. Burgart and V. I. Saloutin},
title = {Features of reactions of polyfluorinated ethyl 4-oxo-2-pnenyl-4H-chromene-3-carboxylates with N-nucleophiles},
journal = {Russian Journal of Organic Chemistry},
year = {2013},
volume = {49},
publisher = {Pleiades Publishing},
month = {may},
url = {https://doi.org/10.1134/s1070428013050151},
number = {5},
pages = {719--729},
doi = {10.1134/s1070428013050151}
}
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MLA
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Shcherbakov, K. V., et al. “Features of reactions of polyfluorinated ethyl 4-oxo-2-pnenyl-4H-chromene-3-carboxylates with N-nucleophiles.” Russian Journal of Organic Chemistry, vol. 49, no. 5, May. 2013, pp. 719-729. https://doi.org/10.1134/s1070428013050151.