Synthesis of isomerically pure 3-(5-trifluoromethyl-1,2,3-triazol-4-yl)cinnamic acid derivatives via the reaction of 4-aryl-6-trifluoromethyl-2-pyrones with sodium azide / Usachev Sergey A.,Usachev Boris I.,Eltsov Oleg S.,Sosnovskikh Vyacheslav Y. // TETRAHEDRON. - 2014. - V. 70, l. 46. - P. 8863-8871.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

Treatment of 4-aryl-6-trifluoromethyl-2-pyrones with sodium azide in DMSO afforded the corresponding (Z)-3-(5-trifluoromethyl-1,2,3-triazol-4-yl)cinnamic acids in good yields. Similarly, 4-aryl-3-carbethoxy-6-trifluoromethyl-2-pyrones smoothly reacted with sodium azide in acetonitrile to produce (E)-2-ethoxycarbonyl-3-(5-trifluoromethyl-1,2,3-triazol-4-yl)cinnamic acids in high yields, whereas their reactions in ethanol, accompanied by a configurational change, gave the thermodynamically more stable (Z)-2-ethoxycarbonyl-3-(5-trifluoromethyl-1,2,3-triazol-4-yl)cinnamic acids. (C) 2014 Elsevier Ltd. All rights reserved.

Author keywords:

Pyrones; Sodium azide; Cinnamic acids; 1,2,3-Triazoles; Geometric isomers; Trifluoromethylated heterocycles ONE-POT SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; EFFICIENT SYNTHESIS; 5-FLUOROALKYLATED 1H-1,2,3-TRIAZOLES; BROMODIFLUOROMETHYLATED TRIAZOLE; 6-(TRIFLUOROMETHYL)COMANIC ACID; REGIOSELECTIVE SYNTHESIS; CONVENIENT SYNTHESIS; BUILDING-BLOCKS; 1,2,3-TRIAZOLES

DOI:

10.1016/j.tet.2014.09.093

Web of Science ID:

ISI:000344204700009

Соавторы в МНС:

Другие поля

Поле	Значение
Month	NOV 18
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	ONE-POT SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; EFFICIENT SYNTHESIS; 5-FLUOROALKYLATED 1H-1,2,3-TRIAZOLES; BROMODIFLUOROMETHYLATED TRIAZOLE; 6-(TRIFLUOROMETHYL)COMANIC ACID; REGIOSELECTIVE SYNTHESIS; CONVENIENT SYNTHESIS; BUILDING-BLOCKS; 1,2,3-TRIAZOLES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vy.sosnov-skikh@urfu.ru
ResearcherID-Numbers	Usachev, Sergey/N-2942-2016
Funding-Acknowledgement	Russian Science Foundation {[}14-13-00388]; Ural Federal University
Funding-Text	This work was financially supported by the Russian Science Foundation (Grant 14-13-00388) and by the Ural Federal University (Program of Support of Young Scientists).
Number-of-Cited-References	55
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	22
Journal-ISO	Tetrahedron
Doc-Delivery-Number	AS3UZ