Synthesis of 2-(trifluoroacetyl)chromones and their reactions with 1,2-diamines / Irgashev Roman A.,Safrygin Alexander V.,Ezhikova Marina A.,Kodess Mikhail I.,Roeschenthaler Gerd-Volker,Sosnovskikh Vyacheslav Y. // TETRAHEDRON. - 2015. - V. 71, l. 12. - P. 1822-1830.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

2-(Trifluoroacetyl)chromones were obtained in good yields via the Claisen condensation of 2-hydroxyacetophenones with methyl 2-methoxytetrafluoropropionate, followed by sulfuric acid-mediated deprotection of the reaction products. These compounds react with ethylenediamine in the presence of acetic acid in methanol to produce the target 2-salicyloylmethylene-3-(trifluoromethyl)1,2,5,6-tetrahydropyrazines in 48-61\% yield. In a similar manner, their reactions with o-phenylenedi-amine and 2,3-diaminonaphthaline in refluxing acetic acid gave a mixture of ketoenamine and ketoimine tautomers of the corresponding quinoxaline derivatives in excellent yields. The regioisomeric and tautomeric composition of the pyrido{[}2,3-b]pyrazines prepared from 2-(trifluoroacetyl)chromones and 2,3-diaminopyridine was also investigated. (C) 2015 Elsevier Ltd. All rights reserved.

Author keywords:

Methyl 2-methoxytetrafluoropropionate; 2-(Trifluoroacetyl)chromones; 1,2-Diamines; Pyrazines; Quinoxalines FLUORINE-CONTAINING HETEROCYCLES; CONTAINING NITROGEN-HETEROCYCLES; NICOTINIC-ACID DERIVATIVES; BIOLOGICAL EVALUATION; ANTICANCER ACTIVITY; ORTHO-DIAMINES; 1ST SYNTHESIS; 3-(POLYFLUOROACYL)CHROMONES; CHEMISTRY; TRIFLUOROPYRUVALDEHYDE

DOI:

10.1016/j.tet.2015.02.010

Web of Science ID:

ISI:000350835800007

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAR 25
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	FLUORINE-CONTAINING HETEROCYCLES; CONTAINING NITROGEN-HETEROCYCLES; NICOTINIC-ACID DERIVATIVES; BIOLOGICAL EVALUATION; ANTICANCER ACTIVITY; ORTHO-DIAMINES; 1ST SYNTHESIS; 3-(POLYFLUOROACYL)CHROMONES; CHEMISTRY; TRIFLUOROPYRUVALDEHYDE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vy.sosnovskikh@urfu.ru
ResearcherID-Numbers	Irgashev, Roman/E-5077-2017
ORCID-Numbers	Irgashev, Roman/0000-0002-8428-1748
Funding-Acknowledgement	Russian Foundation for Basic Research {[}14-03-00179]
Funding-Text	This work was financially supported by the Russian Foundation for Basic Research (Grant 14-03-00179) and performed within the State Task from the Ministry of Education and Science of Russian Federation.
Number-of-Cited-References	51
Usage-Count-Since-2013	20
Journal-ISO	Tetrahedron
Doc-Delivery-Number	CD1LG