Reactivity of 1,2,3-triazoles towards sulfonyl chlorides. A novel approach to 1-and 2-sulfonyl-4-azolyl-1,2,3-triazoles / Beryozkina Tetyana V.,Efimov Ilya V.,Fabian Walter M. F.,Beliaev Nikolai A.,Slepukhin Pavel A.,Isenov Maxim L.,Dehaen Wim,Lubec Gert,Eltsov Oleg S.,Fan Zhijin,Thomas Joice,Bakulev Vasiliy A. // TETRAHEDRON. - 2015. - V. 71, l. 36. - P. 6189-6195.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

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. Coriversely, reactions of triazoles 1a,b and oxadiazolyi 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. (C) 2015 Elsevier Ltd. All rights reserved.

Author keywords:

1,2,3-Triazoles; Sulfonyl triazoles; Sulfonyl chlorides; Regioisomeric mixtures MAIN-GROUP THERMOCHEMISTRY; TERMINAL ALKYNES; CATALYZED TRANSANNULATION; NONCOVALENT INTERACTIONS; DENSITY FUNCTIONALS; AZIDES; TRIAZOLES; ELECTROPHILICITY; CYCLOADDITIONS; REARRANGEMENTS

DOI:

10.1016/j.tet.2015.06.088

Web of Science ID:

ISI:000358969400017

Соавторы в МНС:

Другие поля

Поле	Значение
Month	SEP 9
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	MAIN-GROUP THERMOCHEMISTRY; TERMINAL ALKYNES; CATALYZED TRANSANNULATION; NONCOVALENT INTERACTIONS; DENSITY FUNCTIONALS; AZIDES; TRIAZOLES; ELECTROPHILICITY; CYCLOADDITIONS; REARRANGEMENTS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	tetber@mail.ru fanzj@nankai.edu.cn
ResearcherID-Numbers	Efimov, Ilya/H-8741-2016
ORCID-Numbers	Efimov, Ilya/0000-0003-1123-987X
Funding-Acknowledgement	International Science \& Technology Cooperation Program of China {[}2014DFR41030]; National Natural Science Foundation of China {[}21372132]
Funding-Text	Professor Fan Zhijin thanks The International Science \& Technology Cooperation Program of China (2014DFR41030) and the National Natural Science Foundation of China (21372132) for financial support; TVB thanks The Ministry of Education and Science of the Russian Federation (State task 4.1626.2014/K), VAB thanks RFBR (14-03-01033), W.D. thanks the KU Leuven and FWO-Vlaanderen.
Number-of-Cited-References	49
Usage-Count-Last-180-days	4
Usage-Count-Since-2013	42
Journal-ISO	Tetrahedron
Doc-Delivery-Number	CO2ER