Synthesis of 2H‐chromeno[2,3‐d]pyrimidine‐2,4‐(3H)‐diones (10‐Oxa‐5‐deazaflavins) and their use in the oxidation of benzyl alcohol

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Abstract
Treatment of 6‐phenoxyuracil derivatives with the Vilsmeier reagent (dimethylformamide‐phosphorus oxy‐chloride) gave the corresponding 5‐formyl‐6‐phenoxyuracil derivatives or their equivalents (5‐dimethylamino‐methylene‐6‐phenoxyuracil derivatives). Dehydrative cyclization of the above 5‐formyluracils or 5‐dimethyl‐aminomethyleneuracils with polyphosphoric acid gave the corresponding 2H‐chromeno[2,3‐d]pyrimidine‐2,4(3H)‐diones (10‐oxa‐5‐deazaflavins). These 10‐oxa‐5‐deazaflavins showed strong oxidizing power in oxidizing benzyl alcohol even under neutral conditions (without base) to give benzaldehyde, while they were hydro‐genated to 1,5‐dihydro‐10‐oxa‐5‐deazaflavins.

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