An Efficient Synthesis of 1,2,4-Trisubstituted Imidazoles from Arylacetic Acids andN-Arylbenzamidines via Simultaneous C-H and N-H Bond Activation

Abstract

A convenient and effective FeCl 3 catalyzed one-pot three component protocol for the synthesis of 1,2,4-trisubstituted imidazoles from arylacetic acids, N-arylbenzamidines and nitromethane via simultaneous CÀH and NÀH bond activation has been developed. The reaction involves CÀH activation of arylacetic acid to form aromatic aldehyde which on condensation with N-arylbenzamidine gives azadiene. Nitromethane on Michael addition with azadiene produces ring annulated intermediate which upon subsequent cyclization-elimination sequence offers imidazole. The process utilizes readily available arylacetic acids and inexpensive catalyst. This user friendly protocol provided 1,2,4-trisubstituted imidazoles in moderate to good yields with high functional group tolerance and ample substrate scope.[a] S.

Novel Imidazole Phenoxyacetic Acids as Inhibitors of USP30 for Neuroprotection Implication via the Ubiquitin-Rho-110 Fluorometric Assay: Design, Synthesis, and In Silico and Biochemical Assays

“…The progression of the reaction was monitored through TLC. On completion of the reaction confirmed through TLC, the mixture was diluted with excess MeOH and filtered to separate the catalyst, the filtrate was thus concentrated under vacuum and poured onto ice-cold solution of diluted MeOH, and the product was separated out as the precipitate, which was filtered, dried, and purified by column chromatography. − ,− …”