Synthesis of 4-Quinolone N-Oxides via Controlled Partial Hydrogenation of 2-Nitrobenzoyl Enamines

24 May 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

An operationally simple procedure for the synthesis of 2-alkyl-4-quinolone N-oxides, relying on controlled platinum-catalyzed partial hydrogenation of 2-nitrobenzoyl enamines, has been demonstrated. The P. aeruginosa metabolite 2-heptyl-4-quinolone-N-oxide (HQNO) and four analogous products have been prepared in good yield and high purity by this method.

Keywords

N-hydroxy-4-quinolones
4-hydroxyquinoline N-oxides
HQNO
β-enaminones
heterogeneous catalytic hydrogenation

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