Reaction of ?-Naphthol (I) with amido/imido alcohols (II) in ethyl alcohol containing the catalytic quantity of conc. HCl yielded [(2-hydroxynaphthalen-1-yl)alkyl]-arylamides/imides (III) in excellent yields. Interaction of (II) with benzil in a mixture of conc. H2SO4 and glacial CH3COOH (9:1) afforded the target compounds designated as [(2,3-Dihydro-2-oxo-3,3-diphenylnaphtho[2,3-b]furan-9-yl)alkyl] arylamides/imides (IV) in the yields ranging from 52 to 68%. The compounds (IV) were evaluated against five strains of fungi and four strains of bacteria, respectively.