Toward Demonstrating the Synthetic Utility of 7-substituted-quinolin-2(1H)-ones in Organic Synthesis
Abstract
The following research attempted to investigate the utility of using 7-substituted-quinolin-2(1H)-ones in synthesis. Quinolinones are a specific class of heterocyclic compounds with many biological uses due to their ability to interact with different targets such as enzymes, DNA, and ion channels. The Martin Lab has used a two-step synthetic method of acylation-cyclization of meta-substituted anilines to prepare quinolinones that specifically have a substituent on the seventh position carbon. The utility of the 7-substituted-quinolin-2(1H)-ones was demonstrated using many different synthetic techniques and reactions that attempted to modify the 7-substituted quinolinone core to form new products. The main compound of use was 7-bromoquinolin-2(1H)-one. The planned synthetic modifications included: creating an analog of an enzyme inhibitor, amination reactions, and a coupling reaction with a natural product. Throughout this study, the OSMI-4 inhibitor analog was successfully synthesized and characterized. However, there were a few issues in other reactions, specifically at the 7-substituted position. The amination reaction had issues with product isolation and the coupling with a natural product had problems in reactivity to form a carboxylic acid. In these studies, the synthesis of 7-bromoquinolinone was successfully scaled up to 2.69 g and 8.07 g of product, while the 7-iodoquinolinone was scaled up to 3.25 g of product. Future work could focus on improving reaction design, such as exploring syntheses of a quinolinone-ellagic acid conjugate, including protecting the amide proton of the quinolinone starting materials to improve access to the requisite Grignard reagent and carboxylic acid for that synthesis, as well as exploring scale-up and purification of other 7-substituted quinolinones.
Advisor
Martin, Sara
Department
Chemistry
Recommended Citation
Stewart, Jason R., "Toward Demonstrating the Synthetic Utility of 7-substituted-quinolin-2(1H)-ones in Organic Synthesis" (2024). Senior Independent Study Theses. Paper 11167.
https://openworks.wooster.edu/independentstudy/11167
Disciplines
Organic Chemistry
Keywords
Quinolinones, Synthesis, Reactivity, Product Isolation, Scale-Up
Publication Date
2024
Degree Granted
Bachelor of Arts
Document Type
Senior Independent Study Thesis
© Copyright 2024 Jason R. Stewart