SYNTHESIS OF 2H-PYRIDO[l′,2′:1,6]PYRIDO[2,3-d]PYRIMIDINE-2,4(3H)DIONES (“BENT 5-DEAZAFLAVINS”) AND THEIR USE IN OXIDATION OF ALCOHOL AND AMINE

Treatment of 6-chloro-5-formyluracils with 2-benzylpyridines in dimethylformamide gave the corresponding 2H-pyrido[1′,2′:1,6]pyrido[2,3-d.]pyrimidine-2 ,4(3H)diones which are a bent type of 5-deazaflavin. Similarly, treatment of 6-chloro-5-formyl-3-methyluracil with 2-aminopyridine gave a 6-azalog of the above bent 5-deazaflavin, 2H-pyrido-[2′,1′:2,3]pyrimido[4,5-d]pyrimidine-2,4(3H)dione. These “bent 5-deazaflavins” showed oxidizing ability toward benzyl alcohol, cyclohexanol and benzylamine giving the corresponding carbonyl compounds.