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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 05: 995 - 999

DOI: https://doi.org/10.6023/cjoc201212009

Articles

Synthesis and Bioactivities of Novel 1,2,4-Triazolo[1,5-a]pyrimidine Derivatives Containing 7-(1,3,4-Oxadiazolyl)thioether Moiety

  • Bao Xiaoping ,
  • Lin Xuanfu ,
  • Jian Junyou ,
  • Zhang Feng ,
  • Zou Linbo
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  • Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025

Received date: 2012-12-06

  Revised date: 2013-01-25

  Online published: 2013-02-05

Supported by

Project supported by the Governor's Foundation for Excellent Talents of Science, Technology & Education of Guizhou Province (No. 200817) and the Natural Science Foundation of Guizhou Province (No. 20082265).

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Abstract

Using 2-benzylthio-5-methyl-7-hydroxyl-1,2,4-triazolo[1,5-a]pyrimidine as starting material, ten novel 2-benzyl- thio-5-methyl-7-(5-substituted benzylthio-1,3,4-oxadiazol-2-yl)-methyleneoxyl-1,2,4-triazolo[1,5-a]pyrimidine derivatives 5a～5j were synthesized via sequential reactions of etherification, hydrazinolysis, cyclization and thioetherification. The structures of target compounds were fully characterized by 1H NMR, IR, MS and elemental analysis. The preliminary bioassay showed that some compounds possessed good anti-TMV (tobacco mosaic virus) or certain fungicidal activities in vitro. At the concentration of 500 μg/mL, the inhibition rates of compounds 5b, 5f and 5j against TMV were 45%, 45% and 43%, respectively.

Key words： 1,2,4-triazolo[1,5-a]pyrimidine; 1,3,4-oxadiazole; thioether; synthesis; bioactivity

Cite this article

Bao Xiaoping , Lin Xuanfu , Jian Junyou , Zhang Feng , Zou Linbo . Synthesis and Bioactivities of Novel 1,2,4-Triazolo[1,5-a]pyrimidine Derivatives Containing 7-(1,3,4-Oxadiazolyl)thioether Moiety[J]. Chinese Journal of Organic Chemistry, 2013 , 33(05) : 995 -999 . DOI: 10.6023/cjoc201212009

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