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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 02: 383 - 388

DOI: https://doi.org/10.6023/cjoc201209039

Notes

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
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  • School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384

Received date: 2012-09-28

  Revised date: 2012-10-14

  Online published: 2012-10-26

Supported by

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

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Abstract

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

Cite this article

Peng Chunyong , Xin Chunwei , Li Jianfa , Ji Dan , Bao Xiurong , Lu Junrui . Synthesis and Biological Activities of 1-(4-Methyl)phenyl-5-sub- stituted phenylimino-1,2,3-triazole Carboxylic Acid/Caboxylic Acid Amide[J]. Chinese Journal of Organic Chemistry, 2013 , 33(02) : 383 -388 . DOI: 10.6023/cjoc201209039

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