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An efficient and clean approach for the oxidative amination of indole derivatives with phenothiazines is developed under copper‐catalyzed aerobic conditions. The reaction is carried out via the cross‐coupling of indole radical cation and phenothiazine radical in air. This approach offers a new perspective in the application of phenothiazine as a nitrogen group source for C−N bond formation reactions.

Copper catalyzed aerobic oxidation enables the tandem selective and efficient transformation of N‐pyridylindole for the construction of 11H‐pyrido[2,1‐b]quinazolin‐11‐ones. The reaction shows good efficiency to accomplish the aerobic oxidation. Mechanistic investigation indicated the facile oxidation of N‐pyridylindole underwent the single‐electron‐transfer oxidation, the capture of molecular oxygen and the extrusion of carbon monoxide to deliver the desired 11H‐pyrido[2,1‐b]quinazolin‐11‐ones.

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