The synthesis of thienyl indoyl chalcone produced a novel group of compounds bearing indole and thiophene moieties. The new series of substituted pyridines, 2-pyrazolines, and azepines were synthesized. 2-Aminopyridines were produced by reacting chalcone with active methylene reagents. The chalcone were converted to pyrimidinones. These compounds served as the initial substrate for the synthesis 1-thiocarbamoyl-2-pyrazoline. 1-(4-oxo-5H-thiazolyl)-2-pyrazoline and 1-(4-phenylthiazolyl)-2-pyrazoline were synthesized by treating 1-thiocarbamoyl pyrazoline with chloroacetic acid or phenacyl bromide. The chalcone underwent a reaction with bifunctional agents resulting in the formation of azepines. The compounds were structurally determined with spectral data and they were tested for antimicrobial activity giving reasonable results.