DMSO as a dual carbon synthon in one-pot tandem synthesis of N-alkylated quinazolinones from anthranilamides and acetophenones

Abstract

A new, efficient, metal-free, and DMSO-assisted approach for the synthesis of N-alkylated quinazolinones from readily available 2-aminobenzamide and aryl methyl ketones in the presence of an oxidizing agent has been developed. In this unique tandem reaction, DMSO played a dual role, acting as a solvent as well as a dual carbon synthon, making this process an environmentally benign approach to accessing medicinally prevalent N-alkylated quinazolinones. The DMSO-assisted in situ generation of an iminium cation and α,β-unsaturated ketones from 2-aminobenzamide and aryl methyl ketones, respectively, is the key feature involved in this method. © 2022 The Royal Society of Chemistry.