New methods to access functionalized N-heterocycles
Date
2021
Authors
Patel, Chirag, author
McNally, Andrew, advisor
Bandar, Jeffrey, committee member
Reynolds, Melissa, committee member
Kipper, Matthew, committee member
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Abstract
N-heterocycles are ubiquitous in pharmaceuticals and agrochemicals. Their prevalence is due to the unique properties they can impart to a molecule. Due to their ubiquity, it is vital that synthetic chemists be able to modify the structure of these valuable scaffolds. Despite a great deal of literature on the functionalization of these important motifs, challenges toward the functionalization of N-heterocycles remain. Chapter 1 will highlight the importance of azaarenes in pharmaceuticals and explain the properties that make these structures so prevalent in drugs. Classical and modern methods to functionalize pyridines and diazines will also be discussed. Chapter 2 will describe the development of the phosphonium salt chemistry in the McNally lab and the use of these reactive intermediates to aminate pyridines and diazines via the Staudinger reaction. Chapter 3 will introduce the concept of phosphorus ligand-coupling and briefly describe its previous application toward the synthesis of bis-heterobiaryls. This chapter will also cover the importance of fluoroalkyl groups in both the pharmaceutical and agrochemical industries. Current methods to fluoroalkylate azaarenes will be discussed, and the development of a novel fluoroalkylation strategy via a phosphorus ligand-coupling reaction will be explained. Finally, chapter 4 covers ongoing research into the synthesis of N-alkyl/aryl pyridiniums and their hydrogenation to N-substituted piperidines. The importance of N-substituted piperidines and the limitations to their synthesis are described.
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Subject
scaffolds
azaarenes
pyridines
diazines
heterocyclic phosphonium salts