FORMATION OF 4A,5-DIHYDRO-4A-HYDROXY-5-DEAZAFLAVINS IN THE REACTION OF 1,5-DIHYDRO-5-DEAZAFLAVINS WITH M-CHLOROPERBENZOIC ACID AND THEIR PYRIMIDINE RING CONTRACTION WITH BASE

A new class of 4a, 5-dihydro-4a-hydroxy-5-deazaflavins, which are isosteric and isoelectronic with the flavin pseudobase, was synthesized by the reaction of 1, 5-dihydro-5-deazaflavins with m-chloroperbenzoic acid. The base catalyzed hydrolysis of the 4a, 5-dihydro-4a-hydroxy-5-deazaflavins was carried out to give the corresponding 9, 9a-dihydrooxazolo [4, 5-b] quinolin-2 (4H)-ones.