Methylation of 4-amino-5-methyl-4H-1,2,4-triazole-3-thiol with methyl iodide in sodium methylate afforded unexpected 4-amino-1,3-dimethyl-4H-1,2,4-triazole-5-thione. Reaction of the latter with phenylisothiocyanate gave 6-anilino-1,3-dimethyl[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazol-1-ium hydrosulfide. Acid-catalyzed condensation of 4-amino-1,3-dimethyl-4H-1,2,4-triazole-5-thione with ethyl orthoformate in ethanol lead to the corresponding ethyl N-substituted (5-thioxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)ethanimidoate derivative. Condensation of the latter with anilines or phenylhydrazine gave a group of new 7H-[1,2,4]triazolo[4,3-b][1,2,4]triazol-1-ium hydrosulfides.
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The financial support of this research by Ahvaz Branch, Islamic Azad University is gratefully acknowledged.
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(2), 159–161
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Nikpour, M., Motamedi, H. Сonvenient Access to 1,3-Dimethyl[1,2,4]Triazolo[3,4-b][1,3,4]-Thiadiazol-1-Ium and 7H-[1,2,4]Triazolo[4,3-b][1,2,4]Triazol-1-Ium Salts. Chem Heterocycl Comp 51, 159–161 (2015). https://doi.org/10.1007/s10593-015-1674-9
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DOI: https://doi.org/10.1007/s10593-015-1674-9