Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (02): 383-388.DOI: 10.6023/cjoc201209039 Previous Articles     Next Articles



彭春勇, 辛春伟, 李建发, 戢丹, 鲍秀荣, 卢俊瑞   

  1. 天津理工大学化学化工学院 天津 300384
  • 收稿日期:2012-09-28 修回日期:2012-10-14 发布日期:2012-10-26
  • 通讯作者: 卢俊瑞
  • 基金资助:

    国家自然科学基金(Nos. 21176194, 20976135)资助项目.

Synthesis and Biological Activities of 1-(4-Methyl)phenyl-5-sub- stituted phenylimino-1,2,3-triazole Carboxylic Acid/Caboxylic Acid Amide

Peng Chunyong, Xin Chunwei, Li Jianfa, Ji Dan, Bao Xiurong, Lu Junrui   

  1. School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384
  • Received:2012-09-28 Revised:2012-10-14 Published:2012-10-26
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 20976135, 21176194).

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 (4a4f) 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 (6a6f) 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 4d4f and 6d6f 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