Heterocyclic systems containing bridgehead nitrogen atom: Synthesis and evaluation of bio-activity of thiazolo[3,2-b]-s-triazoles and isomeric thiazolo[2,3-c]-s-triazoles

Abstract

Synthesis of 2-(3'-bromophenyl)-5-(p-bromophenyl) thiazolo[3,2-b]-s-triazoles 4 has been achieved starting from the appropriate 5-mercapto-3-(3'-bromo phenyl)-s-triazole 2. Compound 2 on condensation with α-haloketones gives the ketones 3 which on cyclization with PPA afford 5-(p-bromophenyl)-2-(3'-bromophenyl)thiazolo[3,2-b]-s-triazoles 4 and not the isomeric thiazolo[2,3-c]-s-triazoles 6. This has been established by an unequivocal synthesis of 6 through POCl3 cyclization of 3'-bromobenzoylhydrazino-4-p-bromophenyl-thiazole hydrobromide 5. The diuretic, antibacterial and antifungal activities of some of the compounds have also been evaluated.