The protocatechuic acid-based deep eutectic solvent-mediated green synthesis of 1,2,4,5-tetrasubstituted imidazoles.

Abstract

A novel protocatechuic acid-based deep eutectic solvent (ETPPBr/PCA-DES) was prepared by mixing ethyltriphenylphosphonium bromide (ETPPBr) and protocatechuic acid (PCA = 3,4-dihydroxybenzoic acid), and its structure was fully investigated by using the FT-IR, TGA/DTA, densitometer, eutectic point and 1H NMR techniques. Different molar ratios of ETPPBr to PCA were examined and the eutectic point phase diagram showed that the best ratio for the synthesis of the new DES is the one-to-one ratio of the two starting materials (ETPPBr and PCA). Then, the novel DES was used as a new and capable catalyst for the green synthesis of diverse 1,2,4,5-tetrasubstituted imidazoles a1-a12 from the four-component condensation reaction of phenanthrene-9,10-dione, aromatic amine, aromatic aldehyde, and ammonium acetate with high yields and very short reaction times. High yields and very short reaction times are two advantages of our proposed method compared with the previous reported methods.