Synthesis, characterization and antimicrobial activity of some substituted 1,2,3-triazoles

Two substituted 1,2,3-triazoles 4 and 6 have been synthesized by the 1,3-dipolar cycloaddition reaction of 4-azido-8-(trifluoromethyl)quinoline 2 with ethyl acetoacetate and acetylacetone, respectively. The reaction of 2 with ethyl acetoacetate afforded 1-[8(trifluoromethyl)quinolin-4-yl]-5-methyl-1H-1,2,3-triazole-4-carboxylic acid 3 and with acetylacetone afforded 1-{1-[8-(trifluoromethyl)-quinolin-4-yl]-5-methyl-1H-1,2,3-triazol-4-yl}ethanone 5. Compound 3 is converted into its corresponding acid hydrazide and then condensed with different aromatic aldehydes to yield Schiff's base, N-[1-arylmethylene]-1-[8-(trifluoromethyl)quinolin-4-yl]-5-methyl-1H-1,2,3-triazole4-carbohydrazides 4. Compound 5 is condensed with aromatic aldehydes to obtain [1-aryl-4-{1-[8-(trifluoromethyl)quinolin-4-yl]-5-methyl-1H- 1,2,3-triazol-4-yl}prop-2-en-1-ones 6. The newly prepared 1,2,3-triazole derivatives 4 and 6 have been characterized by IR, NMR and mass spectral data. These compounds were screened for their antimicrobial activity. (c) 2005 Elsevier SAS. All rights reserved.