Heterocycles are cyclic compounds which contain atoms from at least two different elements. The work in this thesis describes methods we developed for the direct chemical transformation of indole heterocycles with various nitrogen heterocycles forming coupled heterocyclic compounds. The first chapter of this thesis introduces background information of the heterocycles worked with on in our research. The chapter will discuss why the synthesis of these compounds are an interesting research topic. The second chapter discusses the research of metal induced transformations of 4(3H)-quinazolinone. Specifically, the work that has been done in the literature to chemically transform these heterocycles. The last chapter will discuss the investigation indole transformations that our group has developed using various reaction conditions. This will lead into discussion of the various methods that were developed by our group, possible mechanistic pathways, and future direction for this project.