Chromone skeletons are widespread among natural products as well as bioactive molecules. Here, we describe an unprecedented reaction of furo[3,4-b]chromen-9-one with malononitrile to afford 3-(tetrahydrofuran-2-yl)-4H-chromen-4-ones. Experimental data suggest that a sequence of Michael/retro-Michael/nucleophilic addition is involved in this unprecedented transformation.