Coupled Domino Processes: Synthesis of 3,5,8-Trisubstituted Coumarins from Propargyl Vinyl Ethers

The generation of a small and representative library of 3,5,8-trisubstituted coumarins (21 compounds, 7 families, 3 groups) is described. The library was built from the corresponding propargyl vinyl ethers and three different 1,3-dicarbonyl derivatives using a one-pot coupled domino strategy. These coumarins constitute a novel chemotype defined by the presence of a chemical handle in the pyranone ring and a varied substitution pattern adorning the aromatic ring, which includes fluorine- or oxygen-containing functionalities.