Synthesis and the reactions of trifluoromethylated 1,2,3-triketones 2-(het)arylhydrazones and 4,7-dihydroazolo{[}5,1-c]triazines / Khudina OG,Shchegol'kov EV,Burgart YV,Kodess MI,Kazheva ON,Chekhlov AN,Shilov GV,Dyachenko OA,Saloutin VI,Chupakhin ON // JOURNAL OF FLUORINE CHEMISTRY. - 2005. - V. 126, l. 8. - P. 1230-1238.

ISSN/EISSN:

0022-1139 / нет данных

Type:

Article

Abstract:

The coupling of trifluoromethylated 1,3-diketones with (het)aryldiazonium chlorides results mainly in the formation of 1,2,3-triketones 2(het)arylhydrazones while using hetarylamine with a NH-group at the a-position of the heterocycle as the diazonium component gives 4,7dihydroazolo{[}5,1-c]triazines due to cyclization at the trifluoroacetyl fragment. Trifluoromethylated 1,2,3-triketones 2-(het)arylhydrazones and 7-hydroxy-4,7-dihydroazolo{[}5,1 -c]triazines react regio-selectively with methyl hydrazine and phenyl hydrazine to form 3-CF3-pyrazoles. The long-range coupling constants (J(F-H)) of 1-methylpyrazoles and the chemical shifts of trifluoromethyl groups in the F-19 NMR spectra can be used for the determination of regio-isomeric structures of mono(trifluoromethyl)-substituted pyrazoles. 2-(Het)arylhydrazones and 4,7dihydroazolo{[}5,1 -c]triazines with two trifluoromethyl substituents afford the mixtures of cis- and trans-azopyrazoles in the reactions with hydrazines. (c) 2005 Elsevier B.V. All rights reserved.

Author keywords:

cyclizations; regio-sclectivity; heterocycles; isomers HYDRAZINES

DOI:

10.1016/j.jfluchem.2005.06.001

Web of Science ID:

ISI:000231275300015

Соавторы в МНС:

Другие поля

Поле	Значение
Month	AUG
Publisher	ELSEVIER SCIENCE SA
Address	PO BOX 564, 1001 LAUSANNE, SWITZERLAND
Language	English
Keywords-Plus	HYDRAZINES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Inorganic \& Nuclear; Chemistry, Organic
Author-Email	kog@ios.uran.ru
ResearcherID-Numbers	Shchegol'kov, Evgenii/H-6790-2015 Burgart, Yanina/T-8025-2017
ORCID-Numbers	Shchegol'kov, Evgenii/0000-0001-6611-2855 Burgart, Yanina/0000-0001-6061-2410
Number-of-Cited-References	12
Usage-Count-Since-2013	1
Journal-ISO	J. Fluor. Chem.
Doc-Delivery-Number	956CA