Synthesis of pyridines and azaindoles via Diels-Alder reactions of tosyl cyanide with vinyl- and heteroarylallenes

Abstract

Pyridines are an important class of heterocycle with widespread applications in a variety of areas. The efficient synthesis of highly substituted pyridines is an ongoing goal of modem synthetic chemistry. Part I of this thesis describes a new synthetic strategy for the synthesis of highly substituted pyridines and azaindoles involving Diels-Alder reactions of vinyl- and heteroarylallenes with tosyl cyanide. The synthetic elaboration of the various pyridine products via an ipso substitution strategy is also described. Part II of this thesis describes the optimization and scale-up of a reproducible synthesis of 1-iodopropyne, an important building block chemical with widespread applications in a variety of transformations.