Synthesis and properties of 5-hydroxy-1-tolyl(benzyl)-1,2,3-triazoles / Nein Y.I., Glukhareva T.V., Sadovskova K.A., Morzherin Y.Y. // Chemistry of Heterocyclic Compounds. - 2016. - V. 52, l. 9. - P. 716-720.

ISSN:
00093122
Type:
Article
Abstract:
[Figure not available: see fulltext.] 1-Benzyl-N-tolyl-1,2,3-triazole-4-carboxamide was accessed via rearrangement of N-benzyl-1-tolyl-1,2,3-triazole-4-carboxamide. It is shown that by boiling in various solvents an equilibrium between isomeric triazoles and diazomalondiamides is established, and that the equilibrium is shifted toward 1-benzyl-1,2,3-triazole. The two isomeric triazoles are shown to undergo alkylation reactions. For 5-hydroxy-1-tolyl-1,2,3-triazole, the alkylation occurs at position 3 of the heterocycle to form a mesoionic triazol-5-olate, whereas for 1-benzyl-5-hydroxy-1,2,3-triazole, alkylation leads to the formation of a 5-alkoxy derivative. © 2016, Springer Science+Business Media New York.
Author keywords:
1,2,3-triazole; alkylation; diazo compound; mesoionic heterocycles; pericyclic reactions; rearrangement
Index keywords:
нет данных
DOI:
10.1007/s10593-016-1953-0
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Affiliations Ural Federal University named after the First President of Russia B. N. Yeltsin, 19 Mira St, Yekaterinburg, Russian Federation
Author Keywords 1,2,3-triazole; alkylation; diazo compound; mesoionic heterocycles; pericyclic reactions; rearrangement
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Correspondence Address Morzherin, Y.Y.; Ural Federal University named after the First President of Russia B. N. Yeltsin, 19 Mira St, Russian Federation; email: yu.yu.morzherin@urfu.ru
Publisher Springer New York LLC
CODEN CHCCA
Language of Original Document English
Abbreviated Source Title Chem. Heterocycl. Compd.
Source Scopus