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Treatment of 3-methyl-6-phenoxyuracils with the Vilsmeier reagent gave the corresponding 5-formyl-3-methyl-6-phenoxyuracils. Dehydrative cyclization of the above 5-formyluracils with polyphosphoric acid gave 3-methyl-2H-chromeno[2,3-d]pyrimidine-2,4(3H)-diones (3-methyl-5-deaza-10-oxaflavins). These 5-deaza-10-oxaflavins showed strong oxidizing power in oxidizing benzyl alcohol even under neutral conditions to give benzaldehyde, while they were hydrogenated to 1,5-dihydro-5-deaza-10-oxaflavins.
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Yoneda et al. (1980) studied this question.
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