SYNTHESIS OF NEW 1,2,3-TRIAZOL-4-YL-6-SUBSTITUTED-S-TRIAZOLO[3,4-B]-1,3,4 THIADIAZOLE DERIVATIVES VIA DIAZONIUM SALTS

Derivatives of 6-aryl-[5-methyl-1-(4-methoxy phenyl)-1,2,3-triazol-4-yl-s-triazolo[3,4-b]-1,3,4- Thiadiazoles (9) and (10) were synthesized by treating p-anisidine with sodium nitrite followed by the addition of sodium azide. Treating azide compound (3) with ethylacetoacetate yielded 1,2,3- triazolo-4-carboxylic acid (4), which was converted to ester (5) using absolute ethanol. Treating the ester with hydrazine hydrate afforded the acid hydrazide derivative (6), which was reacted with CS2 and KOH to produce the salt potassium dithiocarbazate (7). Addition of hydrazine to the salt produced 1-amino-2-mercapto-5-[5-methyl-1-(4-methoxy phenyl) –1,2,3-triazol-4-yl]-1,3,4-triazole (8). Treating (8) with p-chlorobenzoic acid and anisic acid afforded the target compounds (9) and (10).