Synthesis and Characterization of a Novel Ionic Liquid Based on N,N,N,N-tetramethylethylenediamine and its Application in the Synthesis of 1,8-dioxo-octahydro Xanthenes.

Abstract

In this work, we synthesized and characterized a novel Brönsted acidic ionic liquid from the reaction of N, N, N', N'-tetramethylethylenediamine with chlorosulfonic acid and explored its catalytic activity in 1, 8-dioxo-octahydroxanthenes synthesis. Dimedone, aryl aldehydes, and the ionic liquid as the catalyst were reacted under solvent-free conditions. The progressive of the reaction was monitored by a thin layer of chromatography (ethyl acetate/n-hexane = 1/5). All products were characterized as the basis of their spectra data and melting point by comparison with those reported in the literature. The prepared ionic liquid was successfully applied in the synthesis of 1, 8-dioxooctahydroxanthenes in good to high yields on the reaction of aryl aldehyde and dimedone at 120°C under solvent-free conditions. This research demonstrates that the catalyst is impressive for 1, 8-dioxo-octahydroxanthenes synthesis under solvent-free conditions.