TMSOTf-Promoted Synthesis of Quinazolin-4(3H)-one Utilizing DMSO as a Carbon Source
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Date
2023
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Abstract
An 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.