Heating under reflux a mixture of ?-naphthol, an amide (I) and benzaldehyde in absolute ethanol containing a catalytic quantity furnished N-[(2-Hydroxynaphthalen-1-yl)phenylmethyl]arylamides/carboxamido/methylarylamides/imides (II) in excellent yields (71 to 77%). Reaction of the compounds (II) with benzoin in dimethyl formamide (DMF) containing a catalytic quantity of triethylamine(TEA) yielded N-[(2,3-Diphenylnaphtho[2,3-b]furan-9-yl)phenylethyl]arylamides/ carboxamidomethyl-arylamides/imides (III) as target molecules in the yields ranging from 60-65%. The target molecules were bioassayed for their antimicrobial activity involving five strains of fungi and four strains of bacteria in vitro.