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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

Mohsen Nikpour, Hassan Motamedi
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Abstract


Methylation of 4-amino-5-methyl-4H-1,2,4-triazole-3-thiol with methyl iodide in the presence of 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.

How to Cite
Nikpour, M.; Motamedi, H. Chem. Heterocycl. Compd. 2015, 51, 159. [Khim. Geterotsikl. Soedin. 2015, 51, 159.]

For this article in the English edition see DOI 10.1007/s10593-015-1674-9


Keywords


4-amino-5-methyl-4H-1,2,4-triazole-3-thiol; 4-amino-1,3-dimethyl-4H-1,2,4-triazole-5-thione; ethyl (1,3-dimethyl-5-thioxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)imidoformate; [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole; [1,2,4]triazolo[4,3-b][1,2,4]triazole

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