A Convenient Approach to CF3-Containing N-Heterocycles Based on 2-Methoxy-2-methyl-5-(trifluoromethyl)furan-3(2H)-one / Bazhin Denis N.,Kudyakova Yulia S.,Roeschenthaler Gerd-Volker,Burgart Yanina V.,Slepukhin Pavel A.,Isenov Maksim L.,Saloutin Victor I.,Charushin Valery N. // EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - 2015. - V. , l. 23. - P. 5236-5245.

ISSN/EISSN:

1434-193X / 1099-0690

Type:

Article

Abstract:

New synthetic routes to trifluoromethylated N-heterocycles based on condensations of 2-methoxy-2-methyl-5-(trifluoromethyl)furan-3(2H)-one with bifunctional N-nucleophiles are described. For the first time, trifluoromethyl-containing pyrazoles, pyrazolines and isoxazolines bearing hydrazone or oxime groups could be obtained by a one-pot strategy based on reactions of 5-(trifluoromethyl)furan-3(2H)-one with two equivalents of the corresponding hydrazines or hydroxylamine in the presence of an acid. The interaction of furan-3(2H)-one with ureas proceeded under mild conditions to furnish 1H-furo{[}2,3-d]imidazol-2(3H)-one derivatives in good yield. Further, a trifluoromethyl-containing quinoxaline derivative was obtained by condensation of furan-3(2H)-one with ortho-phenylenediamine.

Author keywords:

Nitrogen heterocycles; Oxygen heterocycles; Fluorine; Transimination; Cyclization ONE-POT SYNTHESIS; SLAGENINS A-C; REGIOSELECTIVE SYNTHESIS; FLUOROALKYLATED TRIKETIDES; TEBUFENPYRAD ANALOGS; MEDICINAL CHEMISTRY; IMINE METATHESIS; BUILDING-BLOCK; IN-SITU; PYRAZOLES

DOI:

10.1002/ejoc.201500737

Web of Science ID:

ISI:000359295800023

Соавторы в МНС:

Другие поля

Поле	Значение
Month	AUG
Publisher	WILEY-V C H VERLAG GMBH
Address	POSTFACH 101161, 69451 WEINHEIM, GERMANY
Language	English
EISSN	1099-0690
Keywords-Plus	ONE-POT SYNTHESIS; SLAGENINS A-C; REGIOSELECTIVE SYNTHESIS; FLUOROALKYLATED TRIKETIDES; TEBUFENPYRAD ANALOGS; MEDICINAL CHEMISTRY; IMINE METATHESIS; BUILDING-BLOCK; IN-SITU; PYRAZOLES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	dnbazhin@gmail.com
ResearcherID-Numbers	Kudyakova, Yulia/J-7484-2016 Burgart, Yanina/T-8025-2017 Bazhin, Denis/P-4667-2014
ORCID-Numbers	Kudyakova, Yulia/0000-0003-0637-1606 Burgart, Yanina/0000-0001-6061-2410 Bazhin, Denis/0000-0003-3972-6995
Funding-Acknowledgement	German Deutsche Forschungsgemeinschaft (DFG) {[}RO 362/58-1]
Funding-Text	This work was financially supported by the German Deutsche Forschungsgemeinschaft (DFG), grant number RO 362/58-1. B. D. N. is grateful to one of the reviewer of this article for helpful suggestions.
Number-of-Cited-References	73
Usage-Count-Since-2013	37
Journal-ISO	Eur. J. Org. Chem.
Doc-Delivery-Number	CO6VT