Synthesis of functionalized 2-pyridones via Michael addition and cyclization reaction of amines, alkynes and dialkyl acetylene dicarboxylates

Abstract

The Michael addition and three-component cyclization reaction of amines, alkynes and dialkyl acetylene dicarboxylates to form pyridones has been developed. Aliphatic amines and aromatic amines could selectively be converted into N-alkyl-disubstituted 2-pyridones and N-aryl-trisubstituted 2-pyridones with good yields in the presence of wet ethanol, which means a suitable amount of water is required for this reaction. The Michael addition and cyclization reaction process was confirmed through deuterium-labeling experiments, intermediates isolation and control experiments.