Ring opening of cyclobutane in 1,3-dimethyl-5-methylenebarbituric acid dimer by various nucleophiles

Abstract

The reactivity of cyclobutane moiety in 1,3-dimethyl-5-methylenebarbituric acid dimer (5) towards different nucleophiles was investigated. New derivatives of 5-(substituted methyl)-1,3-dimethylbarbiturate 6–13 were prepared in good yields using various aliphatic amines, cyanide anion, and Ph3P, Ph3As, Ph3Sb. Chemical structures of synthesized products were characterized using NMR, MS, and elemental analysis. The reaction of thiophenoxide and thiocyanate nucleophiles with 5 did not give any new products.