Methodology for the syntheses of pharmaceutically significant functional groups
Name
1121042267-MIT.pdf
Size
21.38 MB
Format
Adobe PDF
Checksum (MD5)
bc29b0c3faf6bc268510a5fd445d697d
Author(s)
Danahy, Kelley E.
Advisor(s)
Timothy F. Jamison.
Date Issued
2019
Publisher
Massachusetts Institute of Technology
Abstract
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.
Description
Thesis: Ph. D., Massachusetts Institute of Technology, Department of Chemistry, 2019
Cataloged from PDF version of thesis.
Includes bibliographical references.
Subjects
Chemistry.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
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