4-Methylphenylazide (1) was synthesized through diazotization reactions from 4-methylaniline, and then reacted with ethyl cyanoacetate or 2-cyano-acetamide to obtain 1-(4-methyl)phenyl-5-amino-1,2,3-triazole carboxylic ethyl ester (2) and 1-(4-methyl)phenyl-5-amino-1,2,3-triazole carboxylic acid amide (5) in strong alkaline condition. Compound 2 hydrolyzed into 1-(4-methyl)phenyl-5-amino-1,2,3-triazole carboxylic acid (3). Then, in weak acidic condition, 1-(4-methyl) phenyl-5-substituted phenylimino-1,2,3-triazole carboxylic acids (4a～4f) were obtained from compound 3 and substituted benzaldehyde. Meanwhile, other 6 novel 1-(4-methyl)phenyl-5-substituted phenylimino-1,2,3-triazole carboxylic acid amides (6a～6f) were synthesized from compound 5 and substituted benzaldehyde. The structures of all compounds have been confirmed by ¹H NMR, ¹³C NMR and IR. The preliminary bioassay showed that, all target compounds possessed efficient antibacterial activities. Especially, the mic values of compounds 4d～4f and 6d～6f were 2～8 μg/mL, lower than fluconazole and triclosan.

Key words: 1-(4-methyl)phenyl-5-amino-1,2,3-triazole carboxylic acid, 1-(4-methyl)phenyl-5-Amino-1,2,3-triazole carboxylic acid amide, 1-(4-methyl)phenyl-5-substituted phenylimino-1,2,3-triazole carboxylic acid/carboxylic acid amide, synthesis, antibacterial activity