The Kinetics and Mechanism of the Reaction between Barbituric Acid and Glycidol, Part I: The Products Analysis

The hydroxyalkyl derivatives of barbituric acid (BA) were formed in the reaction between BA and glycidol (GL). The reaction was performed at BA:GL 1:1, 1:2, and 1:4 molar ratios in DMF or without solvent. The progress of reaction was monitored by determination of the epoxide number and IR and NMR spectroscopy. It was found that primary reactive site of BA was C5 and further nitrogen ring atoms. BA was always involved in keto-enol equilibrium, the latter form being less reactive. The isolated hydroxyalkyl derivatives are useful precursors of oligoetherols with the pyrimidine ring.