Development of Oxidative Dearomatization Enabled Methods to Synthesize Various Heterocycles

Abstract

The structures of FDA approved small-molecule pharmaceuticals are discussed in detail in Chapter 1. Chapter 1.1 focuses on nitrogen-heterocycle containing drugs and Chapter 1.2 focuses on oxygen-heterocycle containing drugs, highlighting the importance and prevalence of these heterocyclic structures. In Chapter 1.3 the structures of molecules utilized in combination drugs are analyzed and discussed. Chapter 2 describes a novel metal-free route to synthesize fluorinated indoles from anilines and hfacac, using a hypervalent iodine oxidant. Chapter 3 shows how the strategy in Chapter 2 was built upon and optimized to create a new synthesis of fluorinated benzofurans. In Chapter 4, a new method to form indoles from 2-allenylanilines is presented, showcasing how lead tetraacetate can be leveraged to achieve cyclization and simultaneous formation of a carbon-nitrogen and carbonoxygen bond. Chapter 5 gives a detailed literature review of how oxirane and oxetane starting materials have been used in ring expansion reactions.