N-Alkylated 2-pyridones are an important class of heterocycles that are found commonly in both natural products and pharmacologically active structures. Interest in these compounds stems from their ability to serve as models for hydrogen bonding, tautomerization, and proton shuttling in both chemical and biological processes. As such, the development of methods for the synthesis of functionally diverse N-alkyl 2-pyridone-containing scaffolds continues to be important. With this goal in mind, our group has developed a suite of reactions that convert O-propargyloxypyridines into a diverse array of useful platforms, including β-iodo N-alkenyl 2-pyridones and α-(N-2-pyridonyl)ketones. These transformations occur upon treatment with either lithium iodide or gold(III) and proceed via either a 5-exo and 6-endo reaction pathway. Under gold(I) catalysis, we have shown that both the 5-exo and 6-endo reaction pathways are accessible simultaneously, as products derived from both modes of cyclization are observed. The evolution of our research program and investigations into the gold(I)-catalyzed system will be discussed.
Matt Sigman, University of Utah
Bringing Modern Data Analysis Tools to Prediction in Catalyst Discovery
Carolyn Anderson, Calvin College
New Methods for the Synthesis of N-Substituted 2-Pyridones