Switching Copper(II)-Catalytic Process for the Selective Access to C3-Imidazolyl- and Pyridylquinoxalin-2(1 H )-ones
Abstract
A simple pseudofour-component reaction catalyzed by CuBr 2 has been developed to deliver C3-imidazoylquinoxalinones with decent yields from quinoxalin-2(1 H )-ones, acetophenones, and ammonium persulfate in DMSO. This process follows a sequence of cross-dehydrogenative coupling/Kornblum oxidation/aza-cyclization, creating selectively four new C–C, two C–N, and C═N bonds. Interestingly, the Kornblum oxidation step can be skipped by simply replacing CuBr 2 with Cu(OAc) 2 . This alteration leads to high-value C3-pyridylquinoxalinones. Notably, DMSO serves both as a C–H source for pyridine ring synthesis and an effective solvent for this conversion. In addition, the acquired 3-imidazolyl- and pyridylquinoxalinones were transmuted into value-added 3-(imidazo[1,2- a ]pyrazin-3-yl)quinoxalinone and 2-sulfonylquinoxalines, showcasing the synthetic utility of our method.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Synthesis and Biological Evaluation
Synthesis and Characterization of Pyrroles
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 6
- Pages
- 2575–2596
- Publication date
- 2 February 2026
- Language
- EN