Development Of New Methods To Synthesize Heterocyclic Compounds

This dissertation is focused on the development of new methods to synthesize imidazoline scaffolds. The work discusses three new procedures developed in the Tepe lab to synthesize trans-oxazoline, trans-imidazoline, and 2,3-disubstituted quinoline scaffolds. In addition, a new guanidine base mediated diastereoselective aziridine synthesis is described in this work. These new synthetic methodologies provide access to compounds that were not easily accessible using previously described methods. Paths to oxazolines and imidazolines via modified Corey-Chaykovsky sulfur ylide chemistry are presented. Here, the sulfonium salts were treated with stable precursors of acyl imines and 1,3-diaza-1,3-butadiene intermediates, respectively, for the oxazoline and imidazoline syntheses. A modified Skraup-type reaction was employed to synthesize 2,3-disubstituted quinoline scaffolds where epoxides were treated with aromatic anilines under mild conditions in the presence of a Lewis acid.