Highly Selective Electrosynthesis of 1 H -1-Hydroxyquinol-4-ones-Synthetic Access to Versatile Natural Antibiotics

1 -1-Hydroxyquinolin-4-ones represent a broad class of biologically active heterocycles having an exocyclic N,O motif. Electrosynthesis offers direct, highly selective, and sustainable access to 1-hydroxyquinol-4-ones by nitro reduction. A versatile synthetic route starting from easily accessible 2-...

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Veröffentlicht in:Organic process research & development 2024-10, Vol.28 (10), p.3922-3928
Hauptverfasser: Prenzel, Tobias, Schwarz, Nils, Hammes, Jasmin, Krähe, Franziska, Pschierer, Sarah, Winter, Johannes, Gálvez-Vázquez, María de Jesús, Schollmeyer, Dieter, Waldvogel, Siegfried R
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Sprache:eng
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Zusammenfassung:1 -1-Hydroxyquinolin-4-ones represent a broad class of biologically active heterocycles having an exocyclic N,O motif. Electrosynthesis offers direct, highly selective, and sustainable access to 1-hydroxyquinol-4-ones by nitro reduction. A versatile synthetic route starting from easily accessible 2-nitrobenzoic acids was established. The broad applicability of this protocol was demonstrated on 26 examples with up to 93% yield, highlighted by the naturally occurring antibiotics Aurachin C and HQNO. The practicability and technical relevance were underlined by multigram scale electrolysis.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.4c00337