OZONOLYSIS OF SUBSTITUTED URACILS

The reactions of cellular substances with ozone is one of the most important subjects in ozone chemistry. Although the ozonization reactions of DNA and RNA are of interest in connection with damage to biological systems, these reactions have received only limited attention.1,2With pyrimidine nucleotides, ozone preferentially attacks the base moieties.3Recently, the ozonolysis of uracils to give 1-acy1-5-hydroxyhydantoins has been reported.4 Since some hydantoins have been used as anticonvulsants, their synthesis is also of interest for medicinal applications. Hydantoins are generally prepared by heating carbonyl compounds with potassium cyanide and ammonium carbonate.5 However, little is known concerning the synthesis of l-acyl-5-hydroxyhydantoins.6In order to obtain new substituted l-acyl-5-hydroxyhydantoins, substituent effects on the ozonolysis of uracils were examined. © 1990, American Chemical Society. All rights reserved.