1,4-Oxazinones as Intermediates in the Construction of Complex Pyridine Products

This thesis describes the construction of complex pyridine products using 1,4-oxazinones as intermediates. The syntheses of polysubstituted pyridines, 2-azaanthraquinones, and natrual product xylanigripone A are reported through the use of a tandem [4+2]/r[4+2] cycloaddition/cycloreversion sequence using 1,4-oxazinones. In addition, two new methods for the construction of 1,4-oxazinones are presented utilizing safe and inexpensive starting materials, providing novel methods to access substrates in the oxazinone family. This work serves to provide new methods to access biologically relevant products and demonstrates the utility of 1,4-oxazinones as versatile intermediates in the construction of pyridine products.