Synthesis and Biological Activities of 3-Substituted-6-pyrazole-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles

doi:10.3724/SP.J.1095.2014.30502

Chinese Journal of Applied Chemistry

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Synthesis and Biological Activities of 3-Substituted-6-pyrazole-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles

AN Yue^*, YAO Mingxing, ZHOU Xiaoxia, LIU Mingyang

(College of Chemistry and Chemical Engineering,Liaoning Normal University,Dalian 116029,China)

Received:2013-10-09 Revised:2014-01-27 Published:2014-08-10 Online:2014-08-10
Contact: Anyue

Abstract

Abstract: The three kinds of 1-methyl-5-substituted-pyrazole-3-carboxylic acid(2a~2c) were obtained by 5-substituted-1H-pyrazole-3-ethyl formate based on methylation and hydrolysis of the ester. Then the six kinds of 3-substituted-4-amino-5-mercapto-1,2,4-triazale(3a~3f) were obtained using the substituted carboxylic acid by a series of reaction; Finally, eighteen novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles compounds(4a~4r) were synthesized by phosphorus chloride treatment of compounds(2a~2c, 3a~3f). The structures of all new compounds were characterized by IR, 1H NMR, 13C NMR and elemental analyses. The preliminary test shows that all the compounds(4a~4r) display auxin activity and fungicidal activity to some extent. Among these compounds, minimum inhibitory concentrations(MIC) were measured for the superior two by antimicrobial.

Key words: pyrazole, triazolo[3,4-b]-thiadiazoles, synthesis, biological activity

CLC Number:

O626.2

AN Yue*, YAO Mingxing, ZHOU Xiaoxia, LIU Mingyang. Synthesis and Biological Activities of 3-Substituted-6-pyrazole-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2014.30502.

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Synthesis and Biological Activities of 3-Substituted-6-pyrazole-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles

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