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

Abstract

The unusual reactivity of key enamine intermediates led to the 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, this methodology allows for the easy preparation of novel derivatives carrying a carboxamide moiety at the C3 position.

Keywords

• 2-benzyl-4(1<i>H</i>)-quinolone
• 2-alkyl-4(1<i>H</i>)-quinolones
• enamines
• enaminones
• naphthalene derivatives