We investigated the radical addition of 4-hydroxycoumarin (la) and 4-hydroxyquinoline (lb) with conjugated dienes (2a-f) mediated by cerium(IV) ammonium nitrate (CAN) resulting in ethenyl substituted 2,3-dihydrofurocoumarin (3a-f) and 3,5-dihydrofuroquinoline (3g, 3h) compounds in moderate to good yields. All compounds were characterized by spectroscopic methods (IR, MS, and H-1 and C-13 NMR) and microanalysis. Antifungal activities of these compounds were investigated against the fungi Candida albicans, C. parapsilosis, C. krusei, C. glabrata, C. tropicalis, and Aspergillus fumigatus.