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■ A Dichotomy in the Reaction of 6-(N-Alkylanilino)-3-methyl-5-nitrouracils with a Mixture of Phospohrous Oxybromide and Dimethylformamide. Formation of Flavins or 5-Deazaflavins

Yoshihru Sakuma, Yoshiko Matsushita, Fumio Yoneda,* and Yoshihiro Nitta

*Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-hon-machi, Kumamoto 862-0973, Japan

Abstract

Treatment of 6-(N-alkylanilino)-3-methyl-5-nitrouracils (I) with a mixture of phosphorus oxybromide and dimethylformamide (POBr₃-DMF) at 80° gave the corresponding isoalloxazines (flavins). On the other hand, treatment of I with POBr3-DMF at 150° led to the exclusive formation of pyrimido[4,5-b]quinoline-2,4(3H,10H)-diones (5-deazaflavins).