What question did this study set out to answer?

The aim is to develop a method for synthesizing 3-arylquinoxaline-2-ones using o-phenylenediamines and diazo esters through cascade processes.

May 9, 2026

Annulative Coupling of o -Phenylenediamine and Diazo Esters: Access to 3-Arylquinoxaline-2-ones

Key Points

The aim is to develop a method for synthesizing 3-arylquinoxaline-2-ones using o-phenylenediamines and diazo esters through cascade processes.
Utilized sequential C-N bond formations under metal-free conditions.
Demonstrated gram-scale synthesis with operational simplicity and broad functional group tolerance.
Included late-stage functionalization techniques such as triflation and Sonogashira coupling.
Achieved moderate to good yields of quinoxalin-2-one derivatives.
Successfully synthesized key precursors for bioactive molecules.
Highlighted the method's practicality through various functionalization steps.

Abstract

-phenylenediamines for the synthesis of 3-arylquinoxalin-2-ones. The transformation proceeds through a cascade process involving sequential C-N bond formations under metal-free conditions, delivering a diverse range of quinoxalin-2-one derivatives in moderate to good yields. The protocol features operational simplicity, mild reaction conditions, and broad functional group tolerance across both diazo esters and diamine partners. Its practicality is demonstrated by gram-scale synthesis and further highlighted through late-stage functionalization, including triflation followed by Sonogashira coupling, as well as thionation to access key precursors of bioactive molecules.

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