N-Vinylpirrolidinone reacts with (E)-ethyl 5-hydroxy-3-(4-oxo-4H-chromen-3-yl) acrylate (1) through a domino reaction similar to that reported reaction for ethyl vinyl ether. Inverse electron demand Diels-Alder (IEDDA)-elimination-IEDDA generates isomeric tetracycles 5 and 6. The assignment of the relative stereochemistry of the products was made by comparing the proton couplings with those obtained by reaction with ethyl vinyl ether.