Abstract
A facile and regioselective Lewis acid-catalyzed cascade annulation of o-hydroxyphenyl propargyl amines with 4-hydroxycoumarin to afford furano[3,2-c]coumarin and pyrano[3,2-c]coumarin derivatives is reported. The reaction presumably proceeds by the conjugate addition of 4-hydroxycoumarin to the in situ-generated alkynyl o-quinone methide and is followed by intramolecular 5-exo-dig and 6-endo-dig annulation to form furano[3,2-c]coumarins and pyrano[3,2-c]coumarins, respectively. The prepared o-hydroxyl substituted pyrano[3,2-c]coumarins could be readily transformed into the corresponding coumarin-derived dioxabicycles by acid-mediated cyclization.
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