TMSOTf‐Promoted Synthesis of Quinazolin‐4(3H)‐one Utilizing DMSO as a Carbon Source

Abstract

AbstractAn efficient TMSOTf‐promoted multicomponent reaction has been developed for the one‐pot synthesis of quinazolin‐4 (3H)‐ones. Using the TMSOTf as a Lewis acid promoter and DMSO as a carbon source, the reaction of isatoic anhydride, primary amines yielded a variety of quinazolines‐4 (3H)‐ones. Additionally, TMSOTf promoted the reaction of 2‐amino‐N‐substituted benzamide with DMSO yielding the same scaffolds in high yields. However, the use of DMSO‐d6 as a solvent in the reaction enabled the incorporation of the −CD moiety in quinazolines‐4 (3H)‐one skeleton. This proves that DMSO plays a twin role as a C1 source and solvent. Various functional groups containing a wide range of quinazolin‐4 (3H)‐ones and other heterocycles were developed employing this methodology. Also, the synthetic methodology has been extended for the synthesis of 3‐(2‐carboxyphenyl)‐4‐(3H)‐quinazolinone, as an anti‐endotoxic drug.