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 S.A., Usachev B.I., Eltsov O.S., Sosnovskikh V.Y. // Tetrahedron. - 2014. - V. 70, l. 46. - P. 8863-8871.

ISSN:
00404020
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. © 2014 Elsevier Ltd. All rights reserved.
Author keywords:
1,2,3-Triazoles; Cinnamic acids; Geometric isomers; Pyrones; Sodium azide; Trifluoromethylated heterocycles
Index keywords:
(4 chlorophenyl)(5 trifluoromethyl 1,2,3 triazol 4 yl)methylenemalonic acid; (4 fluorophenyl)(5 trifluoromethyl 1,2,3 triazol 4 yl)methylenemalonic acid; 1 (5 trifluoromethyl 1,2,3 triazol 4 yl)ethano
DOI:
10.1016/j.tet.2014.09.093
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https://www.scopus.com/inward/record.uri?eid=2-s2.0-84922611195&doi=10.1016%2fj.tet.2014.09.093&partnerID=40&md5=341eea33812b6d6db49a80c63e5cbd5d
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Link https://www.scopus.com/inward/record.uri?eid=2-s2.0-84922611195&doi=10.1016%2fj.tet.2014.09.093&partnerID=40&md5=341eea33812b6d6db49a80c63e5cbd5d
Affiliations Department of Chemistry, Institute of Natural Sciences, Ural Federal University, Ekaterinburg, Russian Federation
Author Keywords 1,2,3-Triazoles; Cinnamic acids; Geometric isomers; Pyrones; Sodium azide; Trifluoromethylated heterocycles
Chemicals/CAS acetonitrile, 75-05-8; dimethyl sulfoxide, 67-68-5; sodium azide, 26628-22-8
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Correspondence Address Sosnovskikh, V.Y.; Department of Chemistry, Institute of Natural Sciences, Ural Federal UniversityRussian Federation
Publisher Elsevier Ltd
CODEN TETRA
Language of Original Document English
Abbreviated Source Title Tetrahedron
Source Scopus