Catalyst Project: Synthesis of Novel Heteroaromatic Compounds Using Pyrroles Generated from Dihydropyridones

Winston-Salem State University, Winston Salem NC

Investigators

Abstract

Catalyst Projects provide support for Historically Black Colleges and Universities to work towards establishing research capacity of faculty to strengthen science, technology, engineering and mathematics undergraduate education and research. It is expected that the award will further the faculty member's research capability, improve research and teaching at the institution. and involve undergraduate students in research experiences. This project at Winston Salem State University will study the organic synthesis of novel compounds. Understanding how to synthesize these compounds will have applications in materials science, pharmaceutical chemistry and other fields. The research will enhance undergraduate student research at Winston Salem State University and further enhance the research capabilities of the institution. In this research, new methodologies and strategies will be developed using the novel pyrrole molecules that will be obtained from the reaction of dihydropyridines with p-toluenesulfonylmethyl isocyanide (TosMIC) reagent. As these underutilized molecules possess such functionalities as pyrrole, ketone and amine, they will further be functionalized to generate novel, complex and fused heteroaromatic scaffolds hosting such privileged motifs as pyrrole, pyridine, indole, thiazoles, indolizines and pyrimidines. Nucleophilic additions to the ketone, electrophilic aromatic substitutions on the pyrrole followed by oxidative aromatization will lead to structurally unique heterocycles in a couple of steps using simple organic reactions. With these strategies, analogs of biologically significant compounds Camphthothein, Isocryptolepine and Tibifarnib will be accessible. This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.