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有机化学
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有机化学 ›› 2000, Vol. 20 ›› Issue (6): 900-904. 上一篇    下一篇

研究论文

α-三唑基查尔酮与苯肼的加成-关环反应研究

刘天麟;谢建华;杨卓鸿   

  1. 南开大学元素有机化学研究所.天津(300071)
  • 发布日期:2000-12-25

Study on the addition-cyclization of α-triazolyl chalcone and phenylhydrazine

Liu Tianlin;Xie Jianhua;Yang Zhaohong   

  1. Nankai Univ, Elementoorgan Chem Lab.Tianjin(300071)
  • Published:2000-12-25

PDF

692

被引次数

30

(Z)或(E)-1,3-二芳基-2-(1H-1,2,4-三唑-1-基)-2-丙烯-1-酮与苯肼在醋酸中反应均生成顺式和反式吡唑啉异构体混合物，但是在三乙胺催化下却只生成反式的异构体。制备了三对顺、反式的1-苯基-3,5-二芳基-4-(1H-1,2,4-三唑-1-基)-2-吡唑啉衍生物，其结构为^1HNMR和元素分析证实，初步论证了经α-氮原子的加成-环化反应机理。

关键词: 三唑P, 查耳酮, 苯肼, 加成反应, 关环反应, 环化, 反应机理, 质子磁共振谱法

The reaction of (Z)&(E)-1,3-diaryl-2-(1H-1,2,4-triazo-1-lyl)-2- propen-1-one and phenylhydrazine in acetic acid medium afforded a mixture of cis and trans 1,3,5-triphenyl-4-triazolyl-2-pyrazoline. In triethylamine, only trans isomer was obtained. Three pairs of cis and trans 1,3,5-triphenyl-4-triazolyl-2-pyrazoline (1a～1c and 2a～2c) were obtained altogether. A reaction machanism via 1,4-addition followed cyclization is postulated.

Key words: PYRRODIAZOLE P, CHALCONE, PHENYLHYDRAZINE, ADDITION REACTION, CYCLIZATION, REACTION MECHANISM, PROTON MAGNETIC RESONANCE SPECTROMETRY

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