TMSOTf‐Promoted Synthesis of Quinazolin‐4(3 <i>H</i> )‐one Utilizing DMSO as a Carbon Source
Sumit Kumar, R. Sivakumar, Kishor Padala, Barnali Maiti
Abstract
Abstract An efficient TMSOTf‐promoted multicomponent reaction has been developed for the one‐pot synthesis of quinazolin‐4 (3 H )‐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 (3 H )‐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‐d 6 as a solvent in the reaction enabled the incorporation of the −CD moiety in quinazolines‐4 (3 H )‐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 (3 H )‐ones and other heterocycles were developed employing this methodology. Also, the synthetic methodology has been extended for the synthesis of 3‐(2‐carboxyphenyl)‐4‐(3 H )‐quinazolinone, as an anti‐endotoxic drug.