Abstract
A one-pot condensation of an aldehyde with 1,2-phenylenediamine or 2-aminothiophenol in dimethyl carbonate at 100 °C under O2 in the presence of catalytic amounts of CeCl3–NaI gave an imine intermediate, which cyclised and dehydrogenated to give 2-arylbenzimidazoles or 2-arylbenzothiazoles in good yields.
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