摘要
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.
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.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2015年第2期446-449,共4页
Chinese Journal of Organic Chemistry
关键词
三唑
苯乙炔
定向合成
triazole
phenyl acetylene
oriented synthesis
