Development of Oxidative Dearomatization Enabled Methods to Synthesize Various Heterocycles
AuthorSmith, David Townsend
AdvisorNjardarson, Jon T.
MetadataShow full item record
PublisherThe University of Arizona.
RightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction, presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
EmbargoRelease after 05/13/2020
AbstractThe 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.
Degree ProgramGraduate College