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Synthesis of bipodal and tripodalpiperidin-4-ones, bipodal, tripodal and tetrapodal 1,4-dihydropyridines have been carried out which is hitherto unreported in the literature. The piperidin-4-ones were reduced to respective piperidin-4-ols by using silica chloride under ultrasonic irradiation which maintained higher yields by acting as an effective supporting polymer. The 2,4-dichloro quinolines have been used as a building blocks for the construction of novel differentially substituted Hantzsch-quinolines, bisindolyl-quinolines and bisquinoline derivatives. All the synthesized compounds were characterized through spectral data and quinolines based derivatives have been preliminarily evaluated for their in vitro antibacterial activity against standard pathological bacterial strains.