Features of reactions of polyfluorinated ethyl 4-oxo-2-pnenyl-4H-chromene-3-carboxylates with N-nucleophiles / Shcherbakov K. V.,Burgart Ya. V.,Saloutin V. I. // RUSSIAN JOURNAL OF ORGANIC CHEMISTRY. - 2013. - V. 49, l. 5. - P. 719-729.

ISSN/EISSN:

1070-4280 / нет данных

Type:

Article

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 C-2 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 C-7 of flavone. In the reaction with 1,2-phenylenediamine 3-{[}(2-aminophenyl)amino]-3-phenyl-2-(2,3,4,5-tetrafluoro-6-hydroxybenz oyl)acrylate was obtained from tetrafluoroflavone and 1H-benzimidazol-2-yl(3,4,5-trifluoro-2-hydroxyphenyl)methanone, from trifluoroflavone.

Author keywords:

4-HYDROXY-5,6,7,8-TETRAFLUOROCOUMARIN DERIVATIVES

DOI:

10.1134/S1070428013050151

Web of Science ID:

ISI:000320230900015

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAY
Publisher	MAIK NAUKA/INTERPERIODICA/SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013-1578 USA
Language	English
Keywords-Plus	4-HYDROXY-5,6,7,8-TETRAFLUOROCOUMARIN DERIVATIVES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	specialk@mail.ru saloutin@ios.uran.ru
ResearcherID-Numbers	Burgart, Yanina/T-8025-2017
ORCID-Numbers	Burgart, Yanina/0000-0001-6061-2410
Funding-Acknowledgement	Russian Federation supporting the leading scientific schools {[}NSh-5505.2012.3]; Ministry of Education and Science of the Russian Federation {[}8430]; Ural Division of the Russian Academy of Sciences {[}12-P-3-1030]
Funding-Text	The study was carried out under the financial support of the program of the President of the Russian Federation supporting the leading scientific schools (grant NSh-5505.2012.3), of the Ministry of Education and Science of the Russian Federation (contract no. 8430), and of the program of the Ural Division of the Russian Academy of Sciences (no. 12-P-3-1030).
Number-of-Cited-References	13
Usage-Count-Since-2013	8
Journal-ISO	Russ. J. Organ. Chem.
Doc-Delivery-Number	161YR