A series of eight 5-aryl/heteryl-7,8,13,14-tetrahydrodibenzo[a,i]phenanthridines, another series of seven novel 5- aryl/heteryl-1,2,3,6,7,8-hexahydrodicyclopenta[b,d]pyridines and two hitherto unknown bridged 2,4-diaryl-3- azabicyclo[3.2.1]octan-8-ones have been synthesised by the condensation of α-tetralone and various aryl/heteryl aldehydes, cyclopentanone and same aryl/heteryl aldehydes and cyclopentanone and two ortho substituted aryl aldehydes respectively in presence of ammonium acetate under methanol and ethanol media under different conditions. All the compounds have been screened for their antimicrobial and antifungal activity with promising results at the outset