Synthesis and properties of 5-hydroxy-1-tolyl(benzyl)-1,2,3-triazoles

Autor:	Ksenia A. Sadovskova, Yuri Yu. Morzherin, Yulia I. Nein, Tatiana V. Glukhareva
Rok vydání:	2016
Předmět:	Pericyclic reaction 1 2 3-Triazole 010405 organic chemistry Stereochemistry Organic Chemistry Mesoionic 02 engineering and technology Alkylation 01 natural sciences Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound 020401 chemical engineering chemistry 0204 chemical engineering
Zdroj:	Chemistry of Heterocyclic Compounds. 52:716-720
ISSN:	1573-8353 0009-3122
DOI:	10.1007/s10593-016-1953-0
Popis:	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.
Databáze:	OpenAIRE
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