Methodology for the syntheses of pharmaceutically significant functional groups
Author(s)Danahy, Kelley E.
Massachusetts Institute of Technology. Department of Chemistry.
Timothy F. Jamison.
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Though pharmaceutical small molecules span a wide range of structures and functions, several common features emerge upon analysis. For example, many medicinal compounds contain combinations of nitrogen-containing heterocycles, polar functional groups such as fluorides or sulfoximines, and stereoisomers that are vital to their bioactivity. As a result, new methods to synthesize these important functional groups are continually in demand. Three main methods to synthesize common pharmacophores are discussed herein: the selective benzylic fluorinations of azaheterocycles via a nitrogen-fluorine halogen bond, the synthesis of sulfoxides and sulfenamides from highly reactive and unstable chloramine in continuous-flow, and partial translation of the process route to enantiopure (S)-naproxen from batch chemistry to continuous-flow.
Thesis: Ph. D., Massachusetts Institute of Technology, Department of Chemistry, 2019Cataloged from PDF version of thesis.Includes bibliographical references.
DepartmentMassachusetts Institute of Technology. Department of Chemistry
Massachusetts Institute of Technology