4-Anilino-5-phenyl-4H-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.