高等学校化学学报

高等学校化学学报 ›› 1989, Vol. 10 ›› Issue (5): 471.

• 研究论文 • 上一篇    下一篇

酰氨基硫脲及其相关杂环衍生物的研究(Ⅹ)—1-(4′-吡啶甲酰基)-4-芳酰胺基硫脲类化合物环化反应的研究

张自义1, 冯小明1, 陈立民1, 孟仟祥2, 高东哲3   

  1. 1. 兰州大学化学系;
    2. 中国科学院兰州地质研究所;
    3. 北京结核病院
  • 收稿日期:1987-09-13 出版日期:1989-05-24 发布日期:1989-05-24
  • 通讯作者: 张自义

Studies on Acylthiosemicarbazides and Related Heterocyclic Compounds (Ⅹ)— Cyclization of1-(4'-Pyridinoyl)-4-Aroylthio- Semicarbazide Derivatives

Zhang Ziyi1, Feng Xiaoming1, Chen Limin1, Meng Qianxiang2, Gao Dongzhe3   

  1. 1. Depertment of Chemistry, Lenzhou University, Lanzhou;
    2. Lanzhou Institute of Geology, Academia Sinica, Lanzhou;
    3. Beijing Tuberculer Institution, Beijing
  • Received:1987-09-13 Online:1989-05-24 Published:1989-05-24

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摘要： 本文研究1-(4′-吡啶甲酰基)-4-芳酰胺基硫脲(Ⅰ)在碱催化条件下的环化反应。结果表明,当(Ⅰ)芳环连接吸电子基如硝基、卤素或推电子取代基如甲基和甲氧基等时,均环化为3-(4′-吡啶基)-4-芳酰基-1,2,4-三唑啉-5-硫酮(Ⅱ),通过质谱裂解碎片分析确定其结构,并初步评价部分化合物对结核菌的抑制作用。

关键词: 酰胺基硫脲, 杂环1, 2, 4-三唑啉-5-硫酮

Abstract: In this work, a series of new 3-(4' -pyridinoyl)-4-aroyl<-1,2,4-tria-zoline-5-thibne( Ⅱ ) have been synthesized by the cyclization of 1-(4' -pyridinoyl)-4-aroylthiosemicarbazides( Ⅰ ) under the catalysis of alkaline medium in good yields. Having studied the reaction of ( Ⅰ ), we found that in all cases when 4-position substituent of aroyl group in compounds( Ⅰ ) was electron-withdrawing group such as NO2,halogen and others, or electron-donating group such as Me, MeOand others,3-(4'-pyridinoyl)-4-aroyl-1,2,4-triazoline-5-thione (Ⅱ) could be obtained. The structures of all compounds prepared were characterized by elemental analysis, IRand 1H NMR. The cyclic orientation of compounds( Ⅰ ) has been comfirmed by the detailed analysis of the fragmentation in mass spectrometry for compounds (Ⅱ ).Preliminary pharmacological examinations show that the new compounds( Ⅱ ) exhibit less antitubercular activity than corresponding parent compounds ( Ⅰ ) except that 3-(4' -pyridinoyl)-4-(2' -fluorine-phenyl)-1, 2, 4-triazoline-5-thione which has a little inhibiting activity.

Key words: Acylthiosemicarbazides, Heterocyclic 1,2,4-triazoline-5-thione

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