DBU-Mediated Domino Annulation Reaction of 2-Amino-4<i>H</i>-chromen-4-ones and Aromatic Aldehydes for Synthesis of Polysubstituted 3-Hydroxy-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridinones
Haiwen Li, Junhu Xin, Yuhang Xue, Cunde Wang
Abstract
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.
Topics & Concepts
ChemistryAnnulationAromatizationIntramolecular forceRing (chemistry)Intermolecular forceNucleophilic additionAtom economyCascade reactionSmiles rearrangementDominoNucleophileMedicinal chemistryStereochemistryCombinatorial chemistryOrganic chemistryMoleculeCatalysisSynthesis of Organic CompoundsBioactive Compounds and Antitumor AgentsSynthesis of heterocyclic compounds