Defense Date

2015

Document Type

Thesis

Degree Name

Master of Science

Department

Chemistry

First Advisor

Dr. B. F. Gupton

Second Advisor

Dr. Scott Gronert

Third Advisor

Dr. Sarah Rutan

Fourth Advisor

Dr. Stephen Fong

Abstract

Abstract

The development of quinolones is described from the first quinolone to the latest fluoroquinolones. Quinolones have generated considerable interest since their discovery because of their antibacterial capabilities. Analogs incorporating the 4-quinolone ring system comprise a largely expanding group of synthetic compounds. The development of antibacterial resistance has created the need for an efficient synthesis of quinolones that can be easily adapted toward the assembly of quinolone based antibacterial drugs.

There are several reported approaches to the 4-quinolone ring system. Many of these methods use expensive starting materials, require the removal of high boiling solvents, or use high temperature conditions (>200°C) for the final cyclization. Our synthesis of 4-quinolones was achieved via continuous flow chemistry using inexpensive starting materials in easily removable solvents, and under mild conditions.

Flow chemistry is the use of technology that allows a continuous flow of reagents to be introduced at various points along a process stream, enabling interaction under highly controlled conditions. By employing this technology we achieved a more rapidly scalable synthesis of 4-quinolones, offering safer reacting conditions and highly reproducible results.

Rights

© The Author

Is Part Of

VCU University Archives

Is Part Of

VCU Theses and Dissertations

Date of Submission

5-18-2015

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