有机化学 ›› 2015, Vol. 35 ›› Issue (2): 446-449.DOI: 10.6023/cjoc201409047 上一篇    下一篇

研究简报

1-甲基-4-苯基-1H-1,2,3-三唑-5-甲酸衍生物的定向合成

刘大安, 裴叔宸, 薛琛琛, 李冉, 吴勇   

  1. 四川大学华西药学院 成都 610041
  • 收稿日期:2014-09-30 修回日期:2014-11-03 出版日期:2015-02-25 发布日期:2014-11-21
  • 通讯作者: 吴勇 E-mail:wyong@scu.edu.cn

Oriented Synthesis of 1-Methyl-4-phenyl-1H-1,2,3-triazole-5-carboxylic Acid

Liu Da'an, Pei Shuchen, Xue Chenchen, Li Ran, Wu Yong   

  1. West China School of Pharmacy, Sichuan University, Chengdu 610041
  • Received:2014-09-30 Revised:2014-11-03 Online:2015-02-25 Published:2014-11-21

1-甲基-4-苯基-1H-1,2,3-三唑-5-甲酸是一类重要的三唑类衍生物, 是多种药物合成的重要中间体. 以苯乙炔为原料, 设计出了一条定向合成1-甲基-4-苯基-1H-1,2,3-三唑-5-甲酸的新方法. 首先苯乙炔与叠氮化钠、碘甲烷在碘化亚铜催化下反应生成1-甲基-4-苯基-1H-1,2,3-三唑, 再依次与正丁基锂、甲酸乙酯反应生成中间体1-甲基-4-苯基-1H-1,2,3-三唑-5-甲醛后直接氧化生成目标化合物. 该合成途径原料易得、总产率较高、后处理操作简便, 具有较高的应用价值.

关键词: 三唑, 苯乙炔, 定向合成

1-Methyl-4-phenyl-1H-1,2,3-triazole-5-formic acid is an important class of triazole derivatives, and also is an important intermediate for the synthesis of various drugs. In this paper, a new method of synthesis of 1-methyl-4-phenyl- 1H-1,2,3-riazole-5-formic acid was designed by using phenyl acetylene as raw materials. Phenyl acetylene reacted with sodium azide and methyl iodide in the presence of copper iodide to generate 1-methyl-4-phenyl-1H-1,2,3-triazole.1-Methyl-4-phenyl-1H-1,2,3-triazole-5-carboxaldehyde was obtained by reacting 1-methyl-4-phenyl-1H-1,2,3-triazole with ethyl formate and butyllithium. Then directly oxidation of 1-methyl-4-phenyl-1H-1,2,3-triazole-5-carboxaldehyde gave the title compound. The synthetic approach has the advantages of easy availability of starting materials, highly stereoselective, easily work-up and good overall yield.

Key words: triazole, phenyl acetylene, oriented synthesis