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A Unified, Microwave‐Assisted, Palladium‐Catalyzed Regioselective Ortho‐monohalogenation of 1‐Alkyl/benzyl‐3‐Phenylquinoxalin‐2(1 <i>H</i> )‐ones

Sandeep Kumar, Prince Prince, Monika Monika, Prashant Kumar, Christophe Len, Brajendra K. Singh

2023ChemistrySelect8 citationsDOI

Abstract

Abstract A Unified, Microwave assisted, Pd‐catalyzed regioselective ortho ‐monohalogenation of 3‐phenylquinoxalin‐2(1 H )‐one derivatives has been disclosed using readily available N ‐halosuccinimides (NXS). The nitrogen atom of quinoxalin‐2(1 H )‐one facilitated as an effective directing group and helped in achieving regioselective mono halogenation at ortho ‐position of 3‐phenyl ring of 3‐phenylquinoxalin‐2(1 H )‐ones. Under mild reaction condition, a wide diversity of mono halogenated products were obtained with wide substrate scope and high functional group tolerance in good yields. Post‐functionalization of the synthesized molecules has been demonstrated.

Topics & Concepts

RegioselectivityHalogenationCatalysisPalladiumRing (chemistry)ChemistryAlkylNitrogen atomFunctional groupSubstrate (aquarium)Medicinal chemistryCombinatorial chemistryOrganic chemistryGeologyOceanographyPolymerCatalytic C–H Functionalization MethodsSynthesis and Biological Evaluation
A Unified, Microwave‐Assisted, Palladium‐Catalyzed Regioselective Ortho‐monohalogenation of 1‐Alkyl/benzyl‐3‐Phenylquinoxalin‐2(1 <i>H</i> )‐ones | Litcius