Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (7): 1611-1616.DOI: 10.6023/cjoc201512042 Previous Articles     Next Articles



徐敏, 史大昕, 刘明星, 张奇, 李加荣   

  1. 北京理工大学化工与环境学院 北京 100081
  • 收稿日期:2015-12-28 修回日期:2016-03-10 发布日期:2016-03-25
  • 通讯作者: 李加荣

Study of 1-Methyl-3-propyl-4-aminopyrazole-5-carbonitrile

Xu Min, Shi Daxin, Liu Mingxing, Zhang Qi, Li Jiarong   

  1. School of Chemical Engineering and Environment, Beijing institute of Technology, Beijing 100081
  • Received:2015-12-28 Revised:2016-03-10 Published:2016-03-25

1-Methyl-3-propyl-4-aminopyrazole-5-carbonitrile was synthesized by using 1-methyl-3-propylpyrazole-5-formic as starting materials in four steps reaction including acylation, dehydration, nitrification and reduction. Then pyrazolopyrimidinone derivatives were obtained from the condensation of 1-methyl-3-propyl-4-aminopyrazole-5-carbonitrile and aldehydes. 1-Methyl-3-propyl-4-nitropyrazole-5-carbonitrile was reduced to amine in the presence of palladium-charcoal. Three intermediate products, hydroxylamine, azoxypyrazole and azopyrazole, were separated and detected with HPLC and HPLC-HRMS during the formation of amine pyrazole. Possible reduction mechanism was proposed. The structures of products were characterized by 1H NMR, 13C NMR, IR spectra and MS.

Key words: 1-methyl-3-propyl-4-aminopyrazole-5-carbonitrile, pyrazolopyrimidinone derivative, reduction mechanism