In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Christopher Pigge of the Department of Chemistry at the University of Iowa will investigate new approaches to construct aza-heterocyclic ring systems via manipulation of alkylidene dihydropyridines (anhydrobases) and related intermediates. While anhydrobases are established compounds, their use as synthetic intermediates has not been extensively explored. In this project both conventional bond forming methods as well as organotransition metal-catalyzed processes (e.g., palladium, rhodium, gold) will be developed in order to harness the synthetic potential of pyridine and related aza-heterocyclic anhydrobases. Development of asymmetric metal-catalyzed transformations also will be undertaken.
This work could lead to more efficient methods for the general preparation of various nitrogen-containing heterocyclic ring systems. These types of compounds are ubiquitous in biologically active natural products and pharmaceuticals. Moreover, aza-heterocyclic derivatives are also common building blocks of functional materials such as organic light emitting diodes and organic semiconductors. Thus, successful execution of this project will impact numerous fields of important contemporary chemical research in areas ranging from organic synthesis and medicinal chemistry to materials research. In addition, this project will provide excellent training of undergraduate and graduate students, including those from groups historically underrepresented in the sciences.
