Synthesis of 2-cyano-5-thiol-1,3,4- thiadiazole

Abstract

In this work 2-cyano-5-thiol-1,3,4-thiadiazole(1) was synthesized from thereaction of diazonium salt of 2-amino -5-thiol-1,3,4-thiadiazolowith(KCN/CuCN) and then was converted into the hydrazino derivative(2) theazomethines (3-6) were syntheized from the corresponding aryl aldehydes andthe hydrazino derivative (2) .Reaction of compounds (3-6)with acetic anhydrideleads to azomethine group opening giving [1-acetyl-2-(5-cyano-1,3,4-thiadiazol-2-yl)*hydrazine]arylo methyl acetate derivatives(7-10). On otherhand treatment ofcompounds(3-6)with 2,4,-dinitrobenzoyl chloride gave compounds (11-13),whichupon refluxing with thiourea in absolute ethanol in the presence of Na2CO3yielded 1-acety l-2-[5-cyano-1,3,4- thiadiazol-2-yl hydrazine]methylimidothiocarbamate derivatives (14 -16) Moreover, thioether derivatives (17-19)have been synthesized by treatment of compound(1)with alkyl or aryl halides.The synthesized compounds were confirmed by their IR and UV spectra.Effect of some synthesized compounds on bacteriastrains was studied.