Task-specific nitrite and azide ionic liquids for the efficient one-pot synthesis of 1,2,3-triazoles from the aniline derivatives

Abstract

An efficient, fast, and straightforward procedure for the synthesis of aromatic azides and in situ preparation of 1,2,3-triazoles under mild conditions is described. Aniline derivatives have been treated with task-specific [bmim]NO(2) and [bmim]N(3) ionic liquids to give the related phenyl azides which, on further in situ reaction with 1,3-diketones and ethylacetoacetate, afforded 1,2,3-triazoles in very good to excellent yields in very short reaction time. This procedure, which generates azides followed by azide in situ cycloaddition with diketone, has become an attractive option. In this protocol, [bmim]N(3) is used instead of the highly toxic reagent NaN(3).