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Anion radicals generated by one-electron reduction of oxime derivatives act as iminyl radical equivalents. That is, the intramolecular C-N bond formation of γ,δ-unsaturated or β-aryl oximes is induced by one electron reduction to give various pyrroles, quinolines, and carbolines. The catalytic electron transfer processes are developed by using hydroquinones or copper reagents as electron donors. Photo-induced electron transfer is also applied to the transformation of γ,δunsaturated oximes to dihydropyrroles.

Synthesis of azaheterocycles by one electron reduction of oximes