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Synthesis of <i>N‐</i>Aryl <i>α</i>‐Ketoamides, <i>α</i>‐Ketoesters, <i>α</i>‐Ketothioesters and Their Applications in Quinoxalinone Preparation

Shweta Singh, Popuri Sureshbabu, Shahulhameed Sabiah, Jeyakumar Kandasamy

2022Asian Journal of Organic Chemistry10 citationsDOI

Abstract

Abstract Synthesis of N‐ aryl α ‐ketoamides, α ‐ketoesters and α ‐ketothioesters were demonstrated from N‐ Ts and N‐ Boc α ‐ketoamides via transamidation and transesterification reactions. The reactions proceeded at room temperature in the presence of DBU and provided the desired products in good to excellent yields in a short time. A regioselective synthesis of biologically relevant quinoxalinones was achieved in good yields from N‐ aryl α ‐ketoamides via nitration followed by reduction reactions.

Topics & Concepts

ChemistryNitrationRegioselectivityArylTransesterificationOrganic chemistryCombinatorial chemistryCatalysisAlkylSynthesis and Biological EvaluationSynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms
Synthesis of <i>N‐</i>Aryl <i>α</i>‐Ketoamides, <i>α</i>‐Ketoesters, <i>α</i>‐Ketothioesters and Their Applications in Quinoxalinone Preparation | Litcius