Ceric ammonium nitrate (CAN) mediated novel dimerizations of 4- hydroxyquinolin-2(1H)-ones: The first example of reactions of oxygencentered radicals from 1,3-dicarbonyl compounds

Article abstract of DOI:10.1016/S0040-4039(98)02644-6

Reactions of 4-hydroxyquinolin-2(1H)-ones (1) and 3-alkylated 44- hydroxyquinolin-2(1H)-ones (2) with CAN in methanol gave quinolin-2(1H)-one dimers 3, 10 and 11 with C-C and C-O linkages between the two nitrogen containing six-member rings, respectively, showing the ambident reactivities of α, α' -dicarbonylalkyl radicals as carbon- and oxygen-centered radicals.