Oxidation of substituted 2-thiouracils and pyrimidine-2-thione with ozone and 3,3-dimethyl-1,2-dioxirane
Ozone and 3,3-dimethyl-1,2-dioxirane react with substituted 2-thiouracils and pyrimidine-2-thione to afford several interesting desulfurized products. The effect of the solvent, protic as opposed to nonprotic, on the course of oxidation was striking.
The ozonolysis of uracils unsubstituted at the 1-position gave new 1-acyl-5-hydroxyhydantoins and 5-hydroxyhydantoins in water, while that of 1-substituted uracils gave the corresponding 5-hydroxyhydantoins in low yields.The structure of 1-acetyl-5-hydroxy-5-methylhydantoin was determined by X-ray crystallography.