Derivatives of 3,4-dihydro-2(1H)-quinolinones are related to riboflavin degradation products, meaning there is expected antimicrobial activity against bacteria strains that lack riboflavin transport mechanisms. 3,4-dihydro-2(1H)-quinolinones have proven to exhibit antibacterial activity against Gram-negative pathogens such as <i>Salmonella</i> and <i>Escherichia coli</i>. This project aims to explore the scope and limitations of synthetic routes toward novel 3,4-dihydro-2(1H)-quinolinone derivatives. The resulting derivatives will then be evaluated for use in future reactions such as nitration, bromination, or Ullmann amination. The previously listed reaction pathways may provide access to intermediates with increased molecular complexity or biological activity. Our previous work has shown that 4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one can arise from N-(4-methylphenyl)-3-methyl-2-butenamide, via a Lewis acid catalyzed cyclization. The next step will be the synthesis 3,4-dihydro-4,4-dimethyl-8-nitro-2(1H)-quinolinone. This product would be the result of 3,4-dihydro-4,4-dimethyl-2(1H)-quinolinone undergoing nitration. The next future step for this project would then be a reduction step to reduce the nitro and the amide group.

Synthetic studies toward 3,4-dihydro-2(1H)-quinolinone derivatives

ACS Spring 2022

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