SYNTHESIS AND PROPERTIES OF PRODUCTS FROM NITRO GROUP SUBSTITUTION IN 4-METHYL-5-NITRO-1,2,4-TRIAZOLE BY 2-(4-HYDROXYPHENYL)ETHANOL

G.Т. Sukhanov, А.G. Sukhanova, K.K. Bosov, I.А. Krupnova, Yu.V. Filippova, V.А. Istoshina
DOI: 10.25699/SSSB.2018.23.17559 Download PDF
Abstract: The process of nucleophilic substitution of the nitro group in 4-methyl-5-nitro-1,2,4-triazole by 2-(4hydroxyphenyl)ethanol furnishes 4-methyl-3-(4-{2-[(4-methyl-4H-1,2,4-triazole-3-yl)oxy]ethyl}phenoxy)-4H-1,2,4-triazole. The main process of the target phenoxytriazole formation is accompanied by a side reaction due to the hydroxide anion attacking the C3 position of the heterocycle whereby a highly reactive 4-methyl-1,2,4-triazole-5-one reacts with the starting nitrotriazole substrate to give 4,4’-dimethyl-4Н,4’Н-[1,3’]bi([1,2,4]triazolyl)-5’-one. The data obtained by the computer-aided prediction of the biological activity of the target phenoxytriazole suggest that further experimental trials of the resultant compound hold promise.
Index terms: nucleophilic substitution, 4-methyl-5-nitro-1,2,4-triazole, Thyrozol, biological activity.

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