The autoxidation reactions of 2-acyl-2,3-dihydroquinazolin-4(1H)-ones >4a and >5a and 2,2′-bis(dihydroquinazolinone) >6a are described. These reactions generate aminyl radicals that undergo β-C–C cleavage, and subsequent reactions of the resulting C-based radicals with O2 lead to diverse products with good selectivity, depending on the structure of the substrate. Oxidation of >4a, in which the 2-acyl group is part of a cyclic acenaphthenone unit, yields a heterocyclic C-hydroperoxylaminal via 1,2-acyl migration. Oxidation of >5a, which contains a 2-acetyl group, yields peracetic acid and a quinazolinone product. Oxidation of >6a forms a bis(quinazolinone) by net dehydrogenation.
展开▼
