1,3,9,11,12,14-Hexa-azapentacene-2,4,8,10(3H,9H,12H,14H,)-tetraones (Doubled 5-Deazaflavins) with Potencial for Oxido Reduction

Article abstract of DOI:10.1039/P19880001809

Condensation of 8-(substitued-amino)1,5-dihydro-5-deazaflavins (3) with 6-chloro-5-formyluracils (4) gave the 1,5-dihydro doubled 5-deazaflavins (5) and 8-(5-formyluracil-6-yl)amino-1,5-dihydro-5-deazaflavins (6).The dehydrogenation of compounds (5) with diethyl azodicarboxylate or the dehydrative cyclization of compounds (6) with Vilsmeier reagent gave the corresponding 1,3,9,11,12,14-hexa-azapentacene-2,4,8,10(3H,9H,12H,14H)-tetraones (doubled 5-deazaflavins) (8).The latter exhibited strong autorecycling oxidation toward cyclopentanol giving, in sunlight under an oxygen atmosphere, cyclopentanone