Synthesis and characterization of some aryl/heteroaryl subtituted 1,2,4-triazolo [3,4-b]-1,3,4-thiadiazoles

In this study, some new 6-substituted thio-3-aryl/heteroaryl-substituted-1,2,4-triazolo[3,4-b]1,3,4-thiadiazole compounds were synthesized. For the synthesis of the molecules, firstly, 3-quinoline carboxylic acid, 4-quinoline carboxylic acid, 1-naphthoic acid or 2-naphthoic acid were reacted with methyl alcohol and sulfuric acid to obtain the corresponding ester compounds. The reaction of the obtained esters with hydrazine hydrate gave the corresponding acid hydrazides. Then, by reacting the hydrazides with carbon disulfide (CS2) in a basic medium, potassium dithiocarbazinate salts were obtained. The obtained potassium dithiocarbazinate salts reacted with hydrazine hydrate to give 5-substituted-4-amino-1,2,4-triazole-3-thiol compounds. The 5-substituted-4-amino-1,2,4-triazole-3-thiol molecules reacted with potassium hydroxide solution dissolved in etanol and carbon disulfide (CS2) to give 3-substituted-1,2,4-triazolo[3,4-b]1,3,4-thiadiazole-6-thiol. As a result of the reaction of the obtained 3-substituted-1,2,4-triazolo[3,4-b]1,3,4-thiadiazole-6-thiol compounds with substituted benzyl halides, 6-((substitutedbenzyl)thio)-3-(naphthyl/quinolinyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole compounds were synthesized. The structures of the obtained compounds were elucidated by 1H NMR, IR, 13C NMR, Mass Spectral data.