A Novel Example of Thermal Oxygenation of Aromatic Hydrocarbons with a Heterocyclic N-Oxide : Unusual Reactivity of Pyrimido[5, 4-g]pteridinetetrone 10-Oxide

Abstract

Aromatic hydrocarbons, i.e., benzene, naphthalene (4), phenanthrene (6), toluene (19), p-xylene (14), mesitylene (18), and durene (21), were oxygenated by a member of a novel class of heterocyclic N-oxides, 1, 3, 6, 8-tetrabutyl-pyrimido[5, 4-g]pteridine-2, 4, 5, 7(1H, 3H, 6H, 8H)-tetrone 10-oxide (1), under certain thermal conditions to give the corresponding products oxygenated in either the benzene ring or the methyl group, presumably via a single-electron transfer process.