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

doi:10.6023/cjoc201409047

Abstract

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

Cite this article

Liu Da'an, Pei Shuchen, Xue Chenchen, Li Ran, Wu Yong. Oriented Synthesis of 1-Methyl-4-phenyl-1H-1,2,3-triazole-5-carboxylic Acid[J]. Chin. J. Org. Chem., 2015, 35(2): 446-449.

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