Synthesis, antimicrobial and anti-inflammatory activities of some 1,2,4-triazolo[3,4- b][1,3,4]thiadiazoles and 1,2,4-triazolo[3,4- b][1,3,4]thiadiazines bearing trichlorophenyl moiety

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The reaction of 2,3,5-trichlorobenzoic acid hydrazide with carbon disulfide and potassium hydroxide followed by treatment with hydrazine hydrate afforded 3-(2,3,5-trichlorophenyl)-4-amino-1,2,4-triazole-5-thione ( 6). Alternatively, this triazole was also synthesized by fusing 2,3,5-trichlorobenzoic acid with thiocarbohydrazide. Condensation of ( 6) with various aromatic carboxylic acids in the presence of phosphorous oxychloride or with phenacyl bromides afforded two series of fused heterocycles namely 6-(substituted aryl)-3-(2,3,5-trichlorophenyl)-[1,2,4]triazolo[3,4- b][1,3,4]thiadizoles ( 7) and 6-(substituted aryl)-3-(2,3,5-trichlorophenyl)-7 H-[1,2,4]triazolo[3,4- b][1,3,4]thiadiazines ( 8), respectively. The structures of these newly synthesized compounds are characterised by elemental analysis, IR, 1H NMR and mass spectroscopic studies. All the synthesized compounds were screened for their antimicrobial and anti-inflammatory activities. Some of the compounds exhibited promising antimicrobial and anti-inflammatory activities.