DBU-Mediated Domino Annulation Reaction of 2-Amino-4H-chromen-4-ones and Aromatic Aldehydes for Synthesis of Polysubstituted 3-Hydroxy-5H-chromeno[2,3-b]pyridinones

A pseudo-three-component annulation reaction of substituted 2-amino-4H-chromen-4-ones with aromatic aldehydes promoted by DBU was investigated to access polysubstituted 5H-chromeno[2,3-b]pyridines. This reaction included a sequential intermolecular nucleophilic addition/Michael cyclization/intramolecular epoxidation/ring opening/aromatization sequence, which possessed excellent step and atom economy in a single operation for generating 3-hydroxy-5H-chromeno[2,3-b]pyridines from readily available substrates.

Automated summary

A pseudo-three-component annulation reaction was investigated to access polysubstituted 5H-chromeno[2,3-b]pyridines. This reaction involved a sequential intermolecular addition/cyclization/epoxidation/ring opening/aromatization sequence, providing an efficient and atom economical approach for the synthesis of 3-hydroxy-5H-chromeno[2,3-b]pyridines from readily available substrates.