NUCLEOPHILIC SUBSTITUTION OF NITRO GROUP IN 1- METHYL- 5-NITRO-1,2,4-TRIAZOLE BY DIAMINOGLYOXIME

I.А. Krupnova, G.Т. Sukhanov, K.K. Bosov, А.G. Sukhanova, Yu.V. Filippova, Е.V. Pivovarova, M.V. Chikina
DOI: 10.25699/SSSB.2021.40.6.011 Download PDF
Abstract: The reaction between 1-methyl-5-nitro-1,2,4-triazome and a concerted bifunctional О-nucleophile – diaminoglyoxime was explored herein. The starting substrate was shown to engage into the SNipso-substitution of the nitro group by the О-nucleophile hydroxyls to furnish a bioactive compound whose single molecule combines different-type pharmacophoric moieties – 1,2,4-triazole heterocycles and NH2 groups. The process came amid competitive reactions to form triazolone and a product from its subsequent reaction with the starting substrate. The PASS Online web-resource was used to perform computer-aided screening, demonstrating that the starting substrate and the reaction products can serve as potential pharmaceutical substances.
Index terms: 1-methyl-5-nitro-1,2,4-triazole, diaminoglyoxime, SNipso-substitution of nitro group, О-nucleophile, N-C bicyclic structure.

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