N-Heterocyclic carbene-catalyzed condensation/oxidation/ cyclization/aromatization cascade for the synthesis of tri- and tetra-substituted imidazoles, By Najmeh Nowrouzi

Research

Title	N-Heterocyclic carbene-catalyzed condensation/oxidation/ cyclization/aromatization cascade for the synthesis of tri- and tetra-substituted imidazoles
Type	Article
Keywords	Benzoin Condensation, Cascade reaction, N-Heterocyclic carbenes, Oxidation, tri(tetra)-Substituted imidazoles.
Journal	Asian Journal of Organic Chemistry
DOI	10.1002/ajoc.202300001
Researchers	Najmeh Nowrouzi (Second researcher) , Dariush Saberi (Third researcher)

Abstract

In this study, a novel and efficient onepot tandem synthesis of 2,4,5-tri- and 1,2,4,5-tetrasubstituted imidazoles is described. In the first step of the sequence, benzil is formed via benzoin condensation catalyzed by N-heterocyclic carbene, followed by in situ aerobic oxidation. Next, it is reacted with another aldehyde and ammonium acetate (or amine) to produce the polysubstituted imidazole. The reaction proceeds smoothly in high yield and short reaction time in ethanol as a green solvent. The current strategy shows high functional group tolerance with respect to aldehydes and avoids the need for ligands and reducing agents. This method allows the synthesis of complex molecules in a one-pot procedure without isolating intermediates.