Synthesis of novel polycarbonyl Schiff bases by ring-opening reaction of ethyl 5-acyl-4-pyrone-2-carboxylates with primary mono- and diamines

Abstract

An approach for the introduction of the tricarbonyl moiety into aromatic, heterocyclic, and aliphatic amines with the use of acylpyrones has been developed for the synthesis and the design of novel polycarbonyl Schiff base ligands, including salphen structures. This Michael addition-ring-opening reaction proceeds under mild conditions (stirring at 0-20 °C) <i>via</i> the attack at the C-6 position of the pyrone ring in good to high yields (up to 99%) with excellent selectivity. The products can be easily isolated by crystallization without the use of chromatography. The scope of the reaction, tautomeric equilibrium of open-chain products, and their cyclization into pyridone structures were investigated.