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Keywords:

  • multicomponent reactions;
  • 3,4-dihydropyridin-2-one;
  • cyanoacetamide;
  • cyclization;
  • imidazole

Abstract

A novel one-pot protocol for the synthesis of valuable 3,4-dihydropyridin-2-ones from the condensation of aldehyde with cyanoacetamide and 1,3-dicarbonyl compounds in the presence of imidazole was developed. A series of aldehydes and 1,3-dicarbonyl compounds were employed to examine the scope of substrates for this protocol. This reaction proceeded through the formation of one ring and four new bonds (two C[BOND]C, one C[BOND]N, one C[DOUBLE BOND]C) via the sequence involving Knoevenagel condensation, Michael addition and intramolecular cyclization with moderate to excellent yields. All new compounds were characterized by IR, 1H NMR, 13C NMR and HRMS.