Photoredox-Catalyzed Radical Coupling of C7-Chloromethyl-Substituted Thiazolino Ring-Fused 2‑Pyridones with Quinoxalinones

• Published in: Journal of organic chemistry Vol. 89; no. 16; pp. 11802 - 11810
• Main Authors: Hellgren, Victor, Singh, Pardeep, Kulkarni, Abhilash, Bagheri, Niusha, Widengren, Jerker, Manavalan, Gopinathan, Almqvist, Fredrik
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 16-08-2024
• ISSN: 0022-3263; 1520-6904; 1520-6904
• DOI: 10.1021/acs.joc.4c01224

We have developed an Ir­(PPy)3 photoredox-catalyzed cross-coupling reaction that allows installation of quinoxalinones at the C7 position of thiazolino ring-fused 2-pyridones (TRPs) under mild conditions. The methodology tolerates various substituted quinoxalinones and biologically relevant substituents on the C8 position of the TRP. The TRP scaffold has large potential in the development of lead compounds, and while the coupled products are interesting from a drug-development perspective, the methodology will be useful for developing more potent and drug-like TRP-based candidates.