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Synthesis of 2 H ‐chromeno[2,3‐ d ]pyrimidine‐2,4‐(3 H )‐diones (10‐Oxa‐5‐deazaflavins) and their use in the oxidation of benzyl alcohol
Author(s) -
Yoneda Fumio,
Hirayama Ryoichi,
Yamashita Machiko
Publication year - 1982
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570190216
Subject(s) - chemistry , oxidizing agent , dimethylformamide , reagent , benzaldehyde , methylene , pyrimidine , medicinal chemistry , chloride , benzyl alcohol , organic chemistry , base (topology) , stereochemistry , solvent , catalysis , mathematical analysis , mathematics
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 2 H ‐chromeno[2,3‐ d ]pyrimidine‐2,4(3 H )‐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.