Annulative Coupling of o -Phenylenediamine and Diazo Esters: Access to 3-Arylquinoxaline-2-ones
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.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Synthesis and Biological Evaluation
Cyclopropane Reaction Mechanisms
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 20
- Pages
- 6901–6910
- Publication date
- 7 May 2026
- Language
- EN