Reactivity of 1,2,3-triazoles towards sulfonyl chlorides. A novel approach to 1- and 2-sulfonyl-4-azolyl-1,2,3-triazoles / Beryozkina T.V., Efimov I.V., Fabian W.M.F., Beliaev N.A., Slepukhin P.A., Isenov M.L., Dehaen W., Lubec G., Eltsov O.S., Fan Z., Thomas J., Bakulev V.A. // Tetrahedron. - 2015. - V. 71, l. 36. - P. 6189-6195.

ISSN:
00404020
Type:
Article
Abstract:
Abstract The reactions of N-unsubstituted triazoles with sulfonyl chlorides afforded mixtures of regioisomeric 1- and 2-sulfonyl-1,2,3-triazoles. In some cases, pure regioisomers were obtained by crystallization of mixtures of isomers. 1,2,3-Triazoles bearing thiadiazole, isoxazole and benzene rings react with mesyl chloride and tosyl chloride to form mainly 1-substituted 1,2,3-triazoles. Conversely, reactions of triazoles 1a,b and oxadiazolyl triazole 1h with more bulky 1-(2,4-dimethylphenyl)sulfonyl chloride affords mainly 2-substitued products. Oxadiazole 1b furnishes an equal mixture of the regioisomeric products 3 and 4 as a result of the reaction with mesyl and tosyl chlorides. Higher temperatures increase the ratio of isomers in favor of the 2-substituted triazole. The ratio of isomers depends on both the nature of the azolyl ring and on the size of the substituent in the sulfonyl chloride. Based on the results of experimental and theoretical data, 1-substituted and 2-substituted 1,2,3-triazoles can be considered as the kinetic and thermodynamic products. © 2015 Elsevier Ltd.
Author keywords:
1,2,3-Triazoles; Regioisomeric mixtures; Sulfonyl chlorides; Sulfonyl triazoles
Index keywords:
1 sulfonyl 4 azolyl 1,2,3 triazole derivative; 1,2,3 triazol 4 yl 1,2,3 thiadiazole derivative; 1,2,3 triazol 4 yl 1,2,4 oxadiazole; 1,2,3 triazol 4 yl isoxazole; 1,2,3 triazole derivative; 2 sulfonyl
DOI:
10.1016/j.tet.2015.06.088
Смотреть в Scopus:
https://www.scopus.com/inward/record.uri?eid=2-s2.0-84937727340&doi=10.1016%2fj.tet.2015.06.088&partnerID=40&md5=f781216bf3fc2305ccf3842cf1409a17
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Поле Значение
Art. No. 26924
Link https://www.scopus.com/inward/record.uri?eid=2-s2.0-84937727340&doi=10.1016%2fj.tet.2015.06.088&partnerID=40&md5=f781216bf3fc2305ccf3842cf1409a17
Affiliations Ural Federal University, 19 Mira St., Yekaterinburg, Russian Federation; Institute of Chemistry, Karl-Franzens-University Graz, Heinrichstrasse 28, Graz, Austria; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Science, 20 S. Kovalevskaya St., Yekaterinburg, Russian Federation; Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven, Belgium; Medical University of Vienna, Department of Pediatrics, 1090, 14 Lazarettgasse, Vienna, Austria; State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Collaborative Innovation Center of Chemical Science and EngineeringTianjin, China
Author Keywords 1,2,3-Triazoles; Regioisomeric mixtures; Sulfonyl chlorides; Sulfonyl triazoles
Chemicals/CAS 1,2,3 triazole derivative, 53897-99-7; benzene, 71-43-2; chloride, 16887-00-6; isoxazole, 288-14-2
Funding Details KU Leuven; 14-03-01033, RFBR, Russian Foundation for Basic Research; 21372132, NSFC, National Natural Science Foundation of China; 4.1626.2014/K, Ministry of Education and Science of the Russian Federation
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Correspondence Address Beryozkina, T.V.; Ural Federal University, 19 Mira St., Russian Federation; email: tetber@mail.ru
Publisher Elsevier Ltd
CODEN TETRA
Language of Original Document English
Abbreviated Source Title Tetrahedron
Source Scopus