Attempted Synthesis of the Pseudomonas aeruginosa Metabolite 2-Benzyl-4(1H)-quinolone and Formation of 3-Methylamino-2-(2-nitrobenzoyl)-4H-naphthalen-1-one as an Unexpected Product

Unusual reactivity of key enamine intermediates led to formation of 3-Methylamino-2-(2-nitrobenzoyl)-4H-naphthalen-1-one as an unexpected product in an attempted synthesis of the P. aeruginosa metabolite 2-benzyl-4(1H)-quinolone. Although the synthesis of the natural product has not been successful, the methodology allowed easy preparation of novel derivatives carrying a carboxamide moiety at the C3-position.