Synthesis and antibacterial activity of some new 4-anilino-5-phenyl-4H-1,2,4-triazole-3-thiol derivatives

4-Anilino-5-phenyl-4 H -1,2,4-triazole-3-thiol ( 1 ) reacted with formaldehyde and different amines to give Mannich bases 2a – i . Treatment of compound 1 with formaldehyde afforded the corresponding 2-hydroxymethyl derivative 3 , which upon its reaction with thionyl chloride yielded the corresponding chloromethyl derivative 4 . Treatment of compound 4 with some thiols gave the corresponding sulfides 5a – f . The ring closure reaction of chloromethyl derivative 4 with hydrazine hydrate, phenyl hydrazine, hydroxylamine, urea and thiourea afforded triazolo-, oxadiazolo- and triazinotriazoles 6 – 10 , respectively.