SYNTHESIS AND PROPERTIES OF 5-HYDROXY-1-TOLYL(BENZYL)-1,2,3-TRIAZOLES

Abstract

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 1benzyl-5-hydroxy-1,2,3-triazole, alkylation leads to the formation of a 5-alkoxy derivative.

Authors: Yulia I. Nein, Tatiana V. Glukhareva, Ksenia A. Sadovskova, Yuri Yu. Morzherin*