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

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.

Updating Dimedone─The Humble Hero of the Organic Laboratory

“…Students will therefore gain a better appreciation that when considering solvation properties, a number of factors need to be considered, including dipole–dipole interactions, hydrogen-bonding interactions (if present), and thermodynamic parameters such as overall entropy and enthalpy. For dimedone, the ratio of tautomers in equilibrium in solution can be determined by 1 H NMR spectroscopy comparing respective integration values, provided that both tautomers are visible in appreciable quantities, as they are in CDCl 3, and this analysis offers a good example of laboratory classes reinforcing NMR interpretations. − IR spectra will similarly show the absence or presence of a hydroxyl stretch depending on the method of acquiring the spectrum.…”

Phenotypic Hit Discovery Oriented Workshop for Undergraduates: Integrating Cutting-Edge Knowledge and Discovery-Based Laboratory Experiences

“…Notable examples include process-oriented guided-inquiry learning and cooperative, problem-based laboratories . In recent years, the number of papers referencing course-based undergraduate research experiences (CUREs) has risen significantly for the medicinal-chemistry curriculum. ,− These CUREs mainly feature incorporating a synthetic organic chemistry experiment into the context of a medicinal chemistry-inspired project. The representative framework of the CUREs is to construct a single experiment or project to teach basic synthetic chemistry skills along with some soft skills.…”

Open Synthesis Network Research in an Undergraduate Laboratory: Development of Benzoxazole Amide Derivatives against Leishmania Parasite

“…6 As with other disciplines, it is important to train medicinal chemists at an undergraduate level with modern strategies that are relevant to the current and future drug discovery landscape. 7 Researchbased drug discovery has been implemented at the undergraduate level with success, for example, for the development of penicillin, 8 amino acid, 9 and quinolone 10 derivatives as new antibiotics, and also for the development of a library of optimized phosphatidylinositide 3-kinase delta inhibitors as anticancer agents. 11 The emergence of more open innovation drug discovery and "crowdsourcing" compounds 12 along with collaborations between academia and industry 13 certainly offer opportunities to integrate real and relevant drug discovery into undergraduate level organic/medicinal chemistry laboratories.…”