Date Approved

11-29-2017

Embargo Period

11-30-2017

Document Type

Thesis

Degree Name

MS Pharmaceutical Sciences

Department

Chemistry and Biochemistry

College

College of Science & Mathematics

First Advisor

Moura-Letts, Gustavo

Second Advisor

Jonnalagadda, Subash

Third Advisor

Keck, Thomas

Subject(s)

Organic compounds--Synthesis

Disciplines

Medicinal-Pharmaceutical Chemistry

Abstract

Nitrogen is found in virtually all valuable chemical compounds. The abundance of atmospheric nitrogen however, is rendered inaccessible because of the strong N-N triple bond, ultimately preventing its practical utilization in synthetic organic synthesis. The development of powerful nitrogen transfer reagents, such as substituted hydroxylamine derivatives, have played an important role in the introduction of nitrogen into valuable chemical scaffolding.

Herein is reported the methodological development of synthetic nitrogen placement into a range of valuable heteroatomic compounds. This work shows that O-Substituted Hydroxylamine can be used to furnish small heteroatomic compounds, particularly nitriles. Whereas, N-Substituted Hydroxylamine can be employed to access both 3- and 5- membered heterocycles. These works highlight the value of substituted hydroxylamines for their nitrogen transfer capability but also for their ability to afford rapid structural complexity.

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