2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ) mediated oxidation-dehydrogenation of 2-aroyl-3,4-dihydro-2H-benzopyrans: synthesis of 2-aroylbenzopyran-4-ones

DDQ mediated an oxidation-dehydrogenation of 2-aroyl-3,4-dihydro-2H-benzopyran prepared from salicylaldehyde to yield 2-aroylbenzopyran-4-one. Stochiometric amount of DDQ, acetic acid and water in refluxing dioxane are the optimal condition for this oxidation-dehydrogenation reaction.A rationally proposed mechanism for this oxidation-dehydrogenation process is based on the isolation of a reaction intermediate viz., 2-benzoyl-8-methoxy-3,4-dihydrobenzopyran-4one and the identification of the 18 O-labled carbonyl group of benzopyran-4-one demonstrating incorporation of labeled H2 18 O.

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