| Despite recent progress, the scope and efficiency of intramolecular hydroamination has not yet reached its full synthetic potential. In particular, cyclizations to form 6-membered rings and applications in the synthesis of aromatic nitrogen heterocycles remain rare, despite the potential to access a variety of medicinally relevant heterocycles. The intramolecular hydroamination of alkynes presented offers a general approach to such nitrogen heterocycles from appropriately substituted acyclic precursors, in which the oxime functionality allows for a milder cyclization event and allows subsequently for the installation of one additional unsaturation (via loss of H2O). The discovery and optimization of an acid-catalyzed, hydroamination-isomerization-aromatization route for the synthesis of pyridines and pyrazines will be presented and discussed.*;*Please refer to dissertation for diagrams. |
