RUI: Reactions of 2-Aminopyrroles

There exists a continuing need for new routes to nitrogen heterocycles--a source of important new drugs. This project continues support for the study of 2-aminopyrroles as precursors for novel nitrogen heterocycles. The 2-aminopyrrole-ring system is electron rich and can act as a dienophile in inverse-electron demand Diels-Alder reactions with electron poor azadienes. Reactions that will lead to a pyrrole ring annulated to a six-membered ring containing one or two nitrogen atoms. The 1,3-dipolar cycloaddition reaction of 2-aminopyrroles has never been reported. Reactions of 2-aminopyrroles with phenyl azides and nitrilimines would lead to interesting heterocyclic systems in which a pyrrole ring is annulated to a five-membered ring containing 2 or 3 nitrogen atoms--heterocyclic compounds that are poorly known, with potential biological activity, and not readily available by other methods. Studies will be carried out to determine if the 1,3-dipolar cycloaddition reaction is concerted or a step-wise process.

With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Michael De Rosa of the Department of Chemistry at Penn State Brandywine. Professor De Rosa's research efforts focus on the chemistry of simple 2-aminopyrroles without further substitution on the ring. Compounds first prepared in Professor De Rosa's research group. Previous studies have discovered several new reactions of 2-aminopyrroles. The proposed work should lead to novel reaction pathways to interesting, and in some cases, previously unknown heterocyclic systems. Undergraduates will carry out experimental work during the summer. It is expected that this project will support the work of 10-12 undergraduates.