Pyrimidine N-Oxides: Syntheses, Structures, and Chemical Properties

The syntheses and reactions of pyrimidines N-oxides are reviewed. Pyrimidines having alkyl, aryl, and alkoxyl groups are convertible to their mono-N-oxides by N-oxidation with an organic peroxy acid. The position of the N-oxide group can be elucidated by physical methods. Pyrimidine N-oxides are highly reactive to various nucleophilic reagents owing to their π-deficient character. The reactivity of a methyl group enhanced by introducing an N-oxide group and the characteristic ring-cleavage of N-oxides are also described