Regioselective synthesis of 5-trifluoromethyl-1,2,3-triazoles via CF3-directed cyclization of 1-trifluoromethyl-1,3-dicarbonyl compounds with azides / Rozin Yury A.,Leban Johann,Dehaen Wim,Nenajdenko Valentine G.,Muzalevskiy Vasiliy M.,Eltsov Oleg S.,Bakulev Vasiliy A. // TETRAHEDRON. - 2012. - V. 68, l. 2. - P. 614-618.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

1-Trifluoromethyl-substituted 1,3-dicarbonyl compounds are shown to undergo 100\% regioselective cyclization in reactions with alkyl and aryl azides to form 4-acyl-5-trifluoromethyl-1,2,3-triazoles. The reaction represents a general method for the synthesis of otherwise difficulty available 4-acyl-5trifluoromethyl-1,2,3-triazoles. The directing role of the trifluoromethyl group is discussed in the light of stepwise and concerted mechanisms for this reaction. (C) 2011 Elsevier Ltd. All rights reserved,

Author keywords:

1-Trifluoromethyl-1,3-dicarbonyl compounds; Azides; {[}3+2] Cycloaddition; 4-Acyl-5-trifluoromethyl-1,2,3-triazoles ONE-POT SYNTHESIS; MEDICINAL CHEMISTRY; CYCLOADDITION; FLUORINATION; DIKETONES; EFFICIENT; DESIGN; BOND

DOI:

10.1016/j.tet.2011.10.110

Web of Science ID:

ISI:000299443900027

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JAN 14
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	ONE-POT SYNTHESIS; MEDICINAL CHEMISTRY; CYCLOADDITION; FLUORINATION; DIKETONES; EFFICIENT; DESIGN; BOND
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vasiliy.bakulev@toslab.com
ResearcherID-Numbers	Nenajdenko, Valentine/R-2277-2016
ORCID-Numbers	Muzalevskiy, Vasiliy/0000-0003-4576-6491
Funding-Acknowledgement	Russian Foundation for Basic Research {[}10-03-00897-a, 11-03-00579-a]; Federal Special Program {[}P962]
Funding-Text	This project was supported by the Russian Foundation for Basic Research (grants no. 10-03-00897-a, 11-03-00579-a) and Federal Special Program (grant P962).
Number-of-Cited-References	50
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	18
Journal-ISO	Tetrahedron
Doc-Delivery-Number	880XM