Expanding the scope of the Bohlmann-Rahtz reaction: new routes to 3-nitropyridines, ?-carbolines, and ß-carbolines

Chapter One opens with an overview of the role of pyridines in the pharmaceutical industry. This is followed by an in-depth survey of literature methods that have been reported for pyridine synthesis, including the Bohlmann-Rahtz reaction. The chapter concludes with the aims of this project. Chapter Two delineates the development and optimization of a new ZnBr2-catalyzed method for the synthesis of 2,3,6-trisubstituted and 2,3,4,6-tetrasubstituted 3-nitropyridines using the Bohlmann-Rahtz reaction. This culminates in the synthesis and characterization of two libraries of 3-nitropyridines. The scope of this new Bohlmann-Rahtz reaction is then expanded to facilitate the synthesis of 2,3-disubstituted and 2,3,4-trisubstituted 3-nitropyridines. Chapter Three describes a DPPE-mediated reaction for the cyclization of 3-nitropyridines into substituted ?-carbolines. The rest of the chapter then describes the development of a PPh3-mediated method for the cyclization of 3-nitropyridines into substituted ß-carbolines. It concludes with the synthesis of the ß-carboline natural product harmine.