高等学校化学学报

高等学校化学学报 ›› 1993, Vol. 14 ›› Issue (2): 209.

• 研究论文 • 上一篇    下一篇

吡唑类化合物的研究(Ⅵ)——吡唑[3,4-e]并-1,2,4-三嗪和吡唑[3,4-e]并-1,2,3,4-四嗪衍生物的合成

鲁源1, 崔秀芳1, 李占江2, 庞吉海2, 蔡孟深2   

  1. 1. 内蒙古医学院;
    2. 北京医科大学药学院, 北京 100083
  • 收稿日期:1992-04-25 修回日期:1992-11-03 出版日期:1993-02-24 发布日期:1993-02-24
  • 通讯作者: 蔡孟深

Studies on Pyrazoles (Ⅵ)——Synthesis of Pyrazolo [3,4-e]-1, 2,4-triazine and Pyrazolo [3,4-e]-1,2,3,4-tetrazine Derivatives

LU Yuan1, GUI Xiu-Fang1, LI Zhan-Jiang2, PANG Ji-Hai2, CAI Meng-Shen2   

  1. 1. Inner Mongolia Medical College;
    2. School of Pharmaceutical Sciences, Beijing Medical Unitvrsity, Beijing, 100083
  • Received:1992-04-25 Revised:1992-11-03 Online:1993-02-24 Published:1993-02-24

PDF (PC)

摘要： 合成了14种1-苯基-3-氨基-5-氧代-4-取代腙吡唑及其关环产物吡唑[3,4-e]并-1,2,4-三嗪和吡唑[3,4-e]并-1,2,3,4-四嗪衍生物,经元素分析、IR、1HNMR和MS确定了其结构,并讨论了一些化合物的lR和1HNMR波谱性质。

关键词: 合成, 吡唑[3, 4-e]并-1, 2, 4-三嗪, 吡唑[3, 4-e]并-1, 2, 3, 4-四嗪

Abstract: Bromination of l-phenyl-3-amino-5-pyrazolone(Ⅰ) in glacial acetic acid gave 1-phenyl-3-amino-4,4-dibromo-5-pyrazolone(Ⅱ).Ⅱ Reacted with a series of substituted hydrazines in hot ethanol to afford l-phenyl-3-amino-5-oxo-4-substituted-hydrazono-pyrazoles(Ⅲa-d).Pyrazolo(3,4-e)-1,2,4-triazine(Ⅳ) was formed by cyclization of 4-ethoxycarbonylhydrazone derivative I,in 5% NaOMe solution.By coupling Iwith diazotized aniline or substituted anilines in the presence of pyri-dine, a series of arylhydrazones(Ⅲ) was prepared with a high yield.These compounds were cyclized by diazotization to give the corresponding 2H-2-phenyl-3-oxo-5H-5-arylpyrazolo [3,4-e]-1,2,3,4-tetrazine derivatives(Va-c).Compound Ⅰreacted with nitrous acid to give 1-phenyl-3-amino-4-ni-troso-5-pyrazolone(Ⅵ).Then Ⅵ was treated with thiosemicarbazide in the boiling pyridine to give 1-phenyl-3-amino-5-oxo-4-thiosemicarbazonopyrazole(Ⅶ).Compound Ⅶ was cyclized under a alkaline condition to give pyrazolo[3,4-e]-l,2,4-triazine(Ⅷ).

Key words: Synthesis, Pyrazolo[3,4-e]-1,2,4-triazine, Pyrazolo[3,4-e]-1,2,4-triazine

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