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

• Main Authors: Abd El-Badih A.G. Ghattas, Hassan M. Moustafa, Elsayed A.A. Hassanein, Bahgat R.M. Hussein
• Format: Article
• Language: English
• Published: Elsevier 2016-11-01
• Series: Arabian Journal of Chemistry
• Subjects: 4-Anilino-5-phenyl-4H-1,2,4-triazole-3-thiol; Mannich bases; Triazolotriazoles; Oxadiazolotriazoles; Triazinotriazoles; Antibacterial activity
• Online Access: http://www.sciencedirect.com/science/article/pii/S1878535212000846
• ISSN: 1878-5352

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.