Synthesis of 10-Arylpyrimido [4,5-b] quinoline-2,4 (3H, 10H) diones (10-Aryl-5-deazaflavins) and Their Use in Oxidations of Alcohols and Amines

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Treatment of aryl-bis (6-anilino-3-methyluracil-5-yl) methanes, which were prepared by the condensation of 6-anilino-3-methyluracils with arylaldehydes, with diethyl azodicarboxylate (DAD) in the presence of sulfolane led to the formation of the corresponding 10-arylprimido [4,5-b] quinoline-2,4 (3H, 10H)-diones (10-aryl-5-deazaflavins). Heating of the methanes alone in sulfolane without DAD gave the corresponding 5-aryl-5-deazaalloxazines. The oxidizing abilities of the 10-aryl-5-deazaflavins thus obtained were examined from both kinetic and synthetic viewpoints. The oxidations of benzyl alcohol and benzylamine by these 5-deazaflavins have been shown to recycle automatically, and more than 100% yield of benzaldehyde (based on the 5-deazaflavins) was obtained.
公益社団法人日本薬学会の論文
1980-10-25