A series of E-(1)-(6-benzoyl-3,5-dimethylfuro[3?,2?:4,5]benzo[b]furan-2-yl)-3-(aryl)-2-propen-1-ones were synthesized by the ClaisenÁSchimdt reaction of 2-acetyl-3,5-dimethyl-6-benzoyl benzodifuran with aromatic/heteroaromatic aldehydes under solvent-free microwave irradiation. All these compounds were characterized by means of their IR, 1 H NMR, and 13 C NMR spectra and elemental analysis. All the compounds were screened for their antibacterial activity.