Synthesis of 5-aryl-2-hydroxy-2-(trifluoromethyl)furan-3(2H)-ones and their reactions with aromatic 1,2-diamines, hydrazine and hydroxylamine / Safrygin Alexander V.,Irgashev Roman A.,Slepukhin Pavel A.,Roeschenthaler Gerd-Volker,Sosnovskikh Vyacheslav Y. // TETRAHEDRON. - 2015. - V. 71, l. 45. - P. 8535-8543.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

2-(Trifluoromethyl)furanones were obtained in good yields via the Claisen condensation of acetophenones with methyl 2-methoxytetrafluoropropionate, followed by sulfuric acid-mediated deprotection of the reaction products. These compounds react with 2,3-diaminopyridine, o-phenylenediamine and 2,3-diaminonaphthalene in refluxing acetic acid to give the corresponding quinoxaline derivatives, the regioisomeric and tautomeric composition of which was investigated. Reactions of 2-(trifluoromethyl) furanones with hydrazines and hydroxylamine proceeded regioselectively and gave pyridazine, pyrazole and isoxazole derivatives in high yields. Their regiochemistry was established by X-ray diffraction analysis. (C) 2015 Elsevier Ltd. All rights reserved.

Author keywords:

2-(Trifluoromethyl)furanones; Nitrogen nucleophiles; Quinoxalines; Pyridazines; Pyrazoles; Isoxazoles METHYL 3,3,3-TRIFLUOROPYRUVATE; REGIOSELECTIVE SYNTHESIS; CHEMISTRY; DERIVATIVES; 2-(TRIFLUOROACETYL)CHROMONES; TRIFLUOROMETHYLKETONES; PRODUCTS; AZIDES

DOI:

10.1016/j.tet.2015.09.035

Web of Science ID:

ISI:000363080800006

Соавторы в МНС:

Другие поля

Поле	Значение
Month	NOV 11
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	METHYL 3,3,3-TRIFLUOROPYRUVATE; REGIOSELECTIVE SYNTHESIS; CHEMISTRY; DERIVATIVES; 2-(TRIFLUOROACETYL)CHROMONES; TRIFLUOROMETHYLKETONES; PRODUCTS; AZIDES
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	29
Usage-Count-Last-180-days	4
Usage-Count-Since-2013	18
Journal-ISO	Tetrahedron
Doc-Delivery-Number	CT8QJ