Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (7): 2026-2034.DOI: 10.6023/cjoc201812019 Previous Articles     Next Articles



苏诗淼a, 朱墨b, 张大强a, 袁德凯a   

  1. a 中国农业大学理学院应用化学系 北京 100193;
    b 首都师范大学化学系 北京 100048
  • 收稿日期:2018-12-11 修回日期:2019-02-28 发布日期:2019-03-21
  • 通讯作者: 袁德凯,
  • 基金资助:


Synthesis and Biological Activity Study of Novel Cyano-containing Multi-substituted Pyrazoles Obtained via Strecker Reaction

Su Shimiaoa, Zhu Mob, Zhang Daqianga, Yuan Dekaia   

  1. a Department of Applied Chemistry, Science College, China Agricultural University, Beijing 100193;
    b Department of Chemistry, Capital Normal University, Beijing 100048
  • Received:2018-12-11 Revised:2019-02-28 Published:2019-03-21
  • Contact: 10.6023/cjoc201812019,
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 20902107).

In order to study the Strecker reaction of multi-substituted amino armorotic heterocycles and the biological activity of the target compounds, the reaction of 3,5-disubstituted pyrazole-4-amine, TMSCN and aldehydes was realized for the first time by the catalysis of anhydrous ZnI2 with 4Å molecular seive. The reaction condition was preliminarily optimized and the substrate scop of aldehydes was studied. 20 target compounds of cyano-containing multi-substituted pyrazoles were obtained with the highest yield of 93.5%, and the sturctures of the compounds were confirmed via 1H NMR, 13C NMR and HRMS methods. Priliminary bioassay of the target compounds showed that 13 target compounds possessed 100% larvicidal activity against mosquito at a concentration of 10×10-3 g/L, and four compounds possessed over 40% larvicidal activity at 5×10-3 g/L, and 10 compounds poccessed weak larvicidal activity against army worm at 500×10-3 g/L with the highest activity of 40%; five compounds were confirmed poccessed good inactivation activity against tobacco mosaic virus (TMV) in vivo with the highest inhibition rate of 31.8%, and four compounds possessed moderate host-protection activity against TMV in vivo with the highest rate of 28.3%; in addition, at a concentration of 50×10-3 g/L, three compounds showed moderate fungicidal activity against Pythium aphanidermatum, Phomopsis asparagi, Phytophora capsic and Rhizoctonia solani in vitro. 4-((1-cyanododecyl)amino)-5-ethyl-N-methyl-1H-pyrazole-3-carboxamide (3t) possessed the highest activity against Phytophora capsic of 62.3%. All the results showed that 3,5-disubstitued pyrazole-4-amine could undergo Strecker reaction smoothly, and this study gave a useful example to explore the Strecker reaction of other multi-substituted aromatic hetreocyclic amines. Additionally, the larvicidal and anti-TMV activity of the target compounds gave some clues in design cyano-containing biological heterocycles.

Key words: multi-substituted pyrazole-4-amine, Strecker reaction, anhydrous ZnI2, cyano-containing pyrazoles, larvicidal activity, anti-TMV activity, fungicidal activity