Synthesis of Quinolone Antibiotic Analogues: A Multistep Synthetic Chemistry Experiment for Undergraduates

Bailie, Alexandra E.; Nortcliffe, Andrew

Abstract

A multistep synthesis of quinolone antibiotic analogues was developed as a laboratory experiment for intermediate/advanced undergraduate students. Students can synthesize a range of desfluoroenoxacin analogues via a five-step sequence. The experiment includes a range of key practical laboratory techniques including thin-layer chromatography (TLC), liquid-liquid extraction, trituration, recrystallization, and the characterization of compounds by IR and NMR spectroscopy. The experiment provides an opportunity for students to carry out fundamental organic chemistry transformations from the curriculum such as the preparation of acyl chlorides, 1,4-conjugate addition-elimination, heterocycle synthesis, nucleophilic aromatic substitution, and ester hydrolysis. The five-step sequence does not require column chromatography and can be adapted to a range of laboratory settings.

Citation

Bailie, A. E., & Nortcliffe, A. (2021). Synthesis of Quinolone Antibiotic Analogues: A Multistep Synthetic Chemistry Experiment for Undergraduates. Journal of Chemical Education, 98(10), 3333-3340. https://doi.org/10.1021/acs.jchemed.1c00459

• Journal Article Type: Article
• Acceptance Date: Sep 7, 2021
• Online Publication Date: Sep 16, 2021
• Publication Date: Oct 12, 2021
• Deposit Date: Nov 9, 2021
• Publicly Available Date: Sep 17, 2022
• Journal: Journal of Chemical Education
• Print ISSN: 0021-9584
• Electronic ISSN: 1938-1328
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 98
• Issue: 10
• Pages: 3333-3340
• DOI: https://doi.org/10.1021/acs.jchemed.1c00459
• Keywords: Organic Chemistry; Upper-Division Undergraduate; Hands-on Learning/Manipulatives; Inquiry-Based/Discover Learning; Synthesis; NMR Spectroscopy; IR Spectroscopy; Medicinal Chemistry
• Public URL: https://nottingham-repository.worktribe.com/output/6675630
• Publisher URL: https://pubs.acs.org/doi/10.1021/acs.jchemed.1c00459
• Additional Information: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Chemical Education, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.jchemed.1c00459