Methodology for the syntheses of pharmaceutically significant functional groups

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.

Name thesis:degree_name

Doctoral

Department dc:contributor.department

Massachusetts Institute of Technology. Department of Chemistry

Grantor dc:publisher

Massachusetts Institute of Technology

Year dc:date.issued

2019

Author dc:creator

• Danahy, Kelley E.

Advisor dc:contributor.advisor

• Timothy F. Jamison.

• Chemistry.

Statement dc:rights

• MIT theses are protected by copyright. They may be viewed, downloaded, or printed from this source but further reproduction or distribution in any format is prohibited without written permission.

Licence dc:rights.uri

• http://dspace.mit.edu/handle/1721.1/7582

Language dc:language.iso

eng

Handle dc:identifier.uri

https://hdl.handle.net/1721.1/122449

OAI identifier oai:identifier

oai:dspace.mit.edu:1721.1/122449