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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 Ph 3 P, Ph 3 As, Ph 3 Sb. 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.

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