Abstract
The domino Knoevenagel/Diels-Alder condensation is a highly efficient strategy for the preparation of heterocyclic compounds. In order to study this reaction with an imine catalyst, a three-component reaction involving aromatic aldehydes, benzylideneacetone and meldrum acid catalyzed by a series of new organocyclic amino acid catalysts was developed. This simple experiment and environmentally friendly method is beneficial for us to get numerous pharmacological multi substituted spiro[5,5]undecane-1,5,9-triones in moderate to good yields (up to 81%) with excellent diastereolectivities (>99:1 dr). Moreover, we expanded the reaction substrates, such as barbituric acid, and the catalytic activity was compared with L-proline that is one of the most commonly secondary amine organocatalysts.
Keywords: Domino reaction, Knoevenagel/Diels-Alder reaction, organocatalyst.
Graphical Abstract
Related Books
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advances in Organic Synthesis
53
2