One-Pot Construction of Indolo[2,3-b]quinoxalines through Ruthenium-Catalyzed Ortho C-H Bond Functionalization of 2-Arylquinoxalines with Sulfonyl Azides

The synthesis of N-substituted indolo[2,3-b]-quinoxalines has been developed through a Ru(II)-catalyzed ortho C-H functionalization of 2-arylquinoxalines with sulfonyl azides and further oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in one pot. This double C-N bond formation strategy provides a new efficient route for the preparation of a series of biologically relevant 6H-indolo[2,3-b]quinoxaline derivatives in up to 94% yield, suggesting a broad substrate scope applicability. The preliminary mechanistic studies reveal that the sequential C-N bond formations proceed through the formation of a five-membered ruthenacyclic intermediate in the first step and a radical mechanism in the second step.

Automated summary

The synthesis of N-substituted indolo[2,3-b]-quinoxalines was achieved through Ru(II)-catalyzed ortho C-H functionalization of 2-arylquinoxalines with sulfonyl azides followed by further oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. This strategy provided a new efficient route for the preparation of biologically relevant compounds with a broad substrate scope. Preliminary mechanistic studies revealed that the C-N bond formations proceed through a five-membered ruthenacyclic intermediate in the first step and a radical mechanism in the second step.