Decisive role of water in efficient noncatalyzed synthesis of polyfunctional 1H-1,2,3-triazoles proceeding from γ-hydroxypropynals

Abstract

A highly efficient method was developed for the synthesis of new polyfunctional 1H-1,2,3-triazoles by the reaction of γ-hydroxypropynals with trimethylsilyl azide in water at room temperature without catalyst. The addition of trimethylsilyl azide to γ-hydroxypropynals occurs regioselectively: Previously unknown hydroxyalkyl-1H-1,2,3-triazolecarbaldehydes have been isolated in 69-96% yields with the prevalence of 1,5-isomers and the content of minor 1,4-isomers equal 9-21%. In the reaction of γ-hydroxypropynals with sodium azide in DMSO the formation of 4-hydroxyalkyl-1H-1,2,3-triazole-5-carbaldehydes is accompanied by the dimerization of initial aldehydes into the corresponding 1,3-dioxolanes.