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3,6-Dimethoxy-2-(cycloamino)anilines undergo 4- or 6-electron oxidations to afford novel ring-fused halogenated benzimidazoles or benzimidazolequinones using H 2 O 2 /HCl or H 2 O 2 /HBr. Cl 2 and Br 2 are capable of the same oxidative transformation to the benzimidazolequinones. Labeling experiments indicate that water is necessary for oxidation of the para-dimethoxybenzenes to the corresponding quinones.

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One-Pot Synthesis of Dihalogenated Ring-Fused Benzimidazolequinones from 3,6-Dimethoxy-2-(cycloamino)anilines Using Hydrogen Peroxide and Hydrohalic Acid