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有机化学 ›› 2006, Vol. 26 ›› Issue (12): 1720-1722. 上一篇    下一篇

研究简报

3,6-二取代苯基-二-1,2,4-三唑并[3,4-b]-1,3,4-噻二唑衍生物的合成

钱建华*,a,b，刘琳b，王道林a，邢锦娟a   

  1. (a渤海大学应用化学省级重点实验室 锦州 121000)
    (b中国科学院金属研究所金属腐蚀与防护国家重点实验室 沈阳 110016)
  • 收稿日期:2006-06-21 修回日期:2006-09-21 发布日期:2006-11-21
  • 通讯作者: 钱建华

Synthesis of 3,6-Bisubstituted Phenyl-bi-1′,2′,4′-triazolo[3,4-b]-1″,3″,4″-thiadiazole De-rivatives

QIAN Jian-Hua*,a,b,LIU Linb,WANG Dao-Lina,XING Jin-Juana   

  1. (a Provincial Key Laboratory for Applied Chemistry, Bohai University, Jinzhou 121000)
    (b State Key Laboratory for Corrosion and Protection, Institute of Metal Re-search,
    Chinese Academy of Sciences, Shenyang 110016)
  • Received:2006-06-21 Revised:2006-09-21 Published:2006-11-21
  • Contact: QIAN Jian-Hua

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以2,5-二巯基-1,3,4-噻二唑为原料, 与水合肼缩合, 生成2,5-二肼基-1,3,4-噻二唑. 2,5-二肼基-1,3,4-噻二唑与苯甲酰氯反应生成2,5-二酰肼基-1,3,4-噻二唑, 以POCl3为环合剂环合酰肼基-1,3,4-噻二唑, 合成3,6-二取代苯基- 二-1,2,4-三唑并[3,4-b]-1,3,4-噻二唑衍生物, 合成的新化合物的结构通过元素分析、红外光谱、核磁共振氢谱和质谱予以证实, 并提出了环化反应机理.

关键词: 三唑并1,3,4-噻二唑, 反应机理, POCl3, 2,5-二肼基-1,3,4-噻二唑

2,5-Bihydrazino-1,3,4-thiadiazole was synthesized by substitution of 2,5-bimercapto-1,3,4-thiadiazole with hydrazine hydrate and reacted with benzoyl chloride to give 2,5-biacylhydrazino-1,3,4-thiadiazole, which was further ring-closed by POCl3 as cyclization agent to synthesize 3,6-bisubstituted phenyl-bi-1′,2′,4′-triazolo[3,4-b]-1″,3″,4″-thiadiazole derivatives. The novel compounds were confirmed by elemental analysis, IR, 1H NMR and MS spectra. The mechanism of cycloreaction was also discussed.

Key words: triazolo-1,3,4-thiadiazole, mechanism, 2,5-bihydrazino-1,3,4-thiadiazol, POCl3