In the present study, a new series of Oxazoline derivatives [5a-5l] were prepared from the N-cyclopentyl indolyl chalcones [4a-4l] with hydroxylamine hydrochloride in presence of base gives 65-78% yield after column purification. The purity of the compounds was checked by TLC in ethylacetate: hexane (3:7). The structures of all the compounds were established by 1H - NMR, IR, LCMS. The synthesized compounds [5a-5l] were evaluated for their anti-microbial activity. Out of 12 compounds reported here, many of them displayed decent anti-bacterial and anti-fungal profiles. We report herewith most prominent molecules 5c, 5d, 5l have been identified as the lead with the most prominent results.