RUI: Reactions of Aminopyrroles

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The Chemical Synthesis Program of the NSF Chemistry Division supports the project by Professor Michael De Rosa in the Department of Chemistry at Penn State-Brandywine. Professor De Rosa studies the synthesis and chemical reactions of a particular class of compounds called aminopyrroles. These molecules are comprised of a ring of carbon atoms with two nitrogen atoms, one within a five-membered ring and one attached as a substituent to the ring. Professor De Rosa uses aminopyrroles are to synthesize more complex molecules that contain two or three rings. These new reactions are important in organic chemistry because they enable efficient and selective transformation of simple molecules to three-dimensional molecules of greater complexity. Many biologically active molecules and pharmaceuticals have three-dimensional structures similar to those constructed by these reactions. More generally, developments in organic chemistry advance the fields of biology, medicine, and materials, as well as promoting economic development and environmental sustainability. Undergraduate student research training performs an indispensable role in the growth of students into scientists. Professor De Rosa works with undergraduate students in this project and prepares them to continue their training in four-year chemistry degree programs and beyond.Aminopyrroles are electron rich substances that were prepared for the first time by Professor De Rosa and his student coworkers. As a consequence of their novel electronic structure, aminopyrroles act as dienophiles in inverse-electron demand Diels-Alder (IEDDA) cycloaddition reactions with azines (azadienes). Complex heterocyclic ring systems are thus rapidly prepared from simple readily available aminopyrroles in good yield and with minimal organic waste. These reactions yield novel heterocycles that are not readily prepared using current methods. This chemistry provides new metal free routes to complex heterocyclic systems, a goal of green chemistry. The possibility that aminopyrroles can be used in multicomponent reactions also is being explored. This research project is carried out in collaboration with undergraduate students, providing valuable experience to enhance their career preparation.