Hunanamycin A (HA) is a natural product isolated from a marine bacterium, Bacillus hunanensis. It has antibacterial properties against gram-negative pathogens such as Salmonella and Escherichia coli. and might also be a useful lead for elucidating novel cancer and HIV treatments. The extraction of HA from its source provides minuscule amounts; to obtain more HA — and to acquire structurally related chemicals for future studies, synthetic routes are under investigation. Our synthesis of HA derivatives began with the amidation of acetic anhydride with 3,4-dimethylaniline to form 3,4-dimethylanilide, which undergoes nitration to provide 4,5-dimethyl-2-nitrophenylacetamide, via mild conditions (bismuth nitrate and acetic anhydride at room temperature). Our current pursuit is to explore the scope and limitation of nitration with 3,4-dihydro-2(1H)-quinolinones and oxindoles. The nitrated products will be evaluated for reduction to amines.

Studies toward synthesizing 3,4-dihydro-2(1H)-quinolinone derivatives

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