Some 1,5 benzodizepines and 1,5 benzothiazepines have been synthesized employing microwave irradiation techniques and evaluated for their antimicrobial activities. 2- Acetyl benzimidazols (1) were reacted with appropriately substituted aromatic aldehydes (2) in the presence of base to furnish substituted chalcones (3a-f). These chalcones were further reacted with ortho phenylenediamine to offered 4-(1H-benzimidazol-2-yl)-2-phenyl-2,3-dihydro-1H-1,5- benzodiazepines (4a-f). Reaction of the chalcones (3a-f) with 2- amino thiophenol yielded substituted 4-(1H-benzimidazol-2-yl)-2-phenyl-2,3-dihydro-1,5-benzothiazepines (5a-f). All the synthesized compounds were characterized by elemental analysis and IR, 1H NMR and Mass spectral data. All the compounds were screened for their antimicrobial activities against gram positive bacteria Staphylococcus aureus, Bacillus subtilis and gram negative bacteria Escherichia coli, Pseudomonas aeruginosa and fungal species like Candida albicans and Aspergillus niger organisms.