Acylaminoacetyl derivatives of active methylene compounds. 2. The cyclization of the acetylaminoacetyl derivatives to α-substituted tetramic acids and the formation of N-acetyl-α-substituted tetramic acids

The reaction of aceturic acid p-nitrophenyl ester with active methylene compounds Y-CH₂-CO₂R has been found to give either the normally expected C-acylation compounds 2 (Y = -CN, -CO₂R, -COCH₃) or N-acetyl-α-Y-substituted tetramic acids 3 (Y = -CO₂R,-COCH₃), depending on the reaction conditions. Moreover, the intramolecular condensation of the C-acylation compounds 2 derived from malonic and acetoacetic esters (Y = -CO₂R, -COCH₃) to α-Y-substituted tetramic acids is shown to proceed through initial cyclization to the corresponding N-acetyl-α-Y-substituted tetramic acids 3 (Y = -CO₂R, -COCH₃).