Efficient Multicomponent Synthesis of Mono-, Bis-, and Tris-1,2,3-triazoles Supported by Hydroxybenzene Scaffolds

Abstract

A versatile one-pot synthesis of a series of mono-, bis- and tris-1,2,3-triazoles supported by commercially available hydroxybenzene scaffolds has been developed employing click chemistry. The multicomponent copper(I)-catalyzed 1,3-dipolar cycloaddition of sodium azide, propargyl bromide, and a para-substituted benzyl derivative yields N-benzyl-functionalized triazoles featuring several electron-donating or electron-withdrawing groups. Despite the preparation of highly substituted molecules, reaction conditions that provides good yields involved room temperature, times that oscillate between 16 and 24 hours, and catalyst loads ranging from 5–10 mol%. The present methodology could be useful for the building up of multi-triazole libraries easily tunable with donor or attractor functional groups.