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Synthesis of Quinazolinones and Benzothiazoles Using α-Keto Acids under Ball Milling

Anoop Sharma, Anoop Sharma, Jitender Singh, Anuj Sharma, Anuj Sharma

2024The Journal of Organic Chemistry12 citationsDOI

Abstract

Mechanochemistry refers to the initiation of chemical reactions via mechanical forces such as milling, grinding, or shearing to achieve the chemical transformations. As a manifestation of mechanocatalysis, herein, an oxidant-free and solvent-free approach for the synthesis of quinazolinones (23 derivatives) and benzothiazoles (23 derivatives) has been developed through stainless-steel-driven decarboxylative acyl radical generation from α-keto acids. A library of 2-arylquinazolinones and 2-arylbenzothiazoles has been prepared in moderate to good yields at room temperature. Moreover, control experiments and XPS studies supported the reduction (by zerovalent iron) of molecular oxygen through the moderate abrasion of balls, which promoted the generation of a superoxide radical anion via a SET process.

Topics & Concepts

MechanochemistryBall millGrindingX-ray photoelectron spectroscopyChemistrySuperoxideSolventOxygenCombinatorial chemistryChemical engineeringMaterials scienceOrganic chemistryMetallurgyEngineeringEnzymeQuinazolinone synthesis and applicationsPhenothiazines and Benzothiazines Synthesis and ActivitiesRadical Photochemical Reactions
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