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

Prenzel, Tobias; Schwarz, Nils; Hammes, Jasmin; Krähe, Franziska; Pschierer, Sarah; Winter, Johannes; Gálvez-Vázquez, María de Jesús; Schollmeyer, Dieter; Waldvogel, Siegfried R. 1
1 Institut für Biologische und Chemische Systeme (IBCS), Karlsruher Institut für Technologie (KIT)

Abstract:

1H-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.


Verlagsausgabe §
DOI: 10.5445/IR/1000176044
Veröffentlicht am 07.11.2024
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische und Chemische Systeme (IBCS)
Publikationstyp Zeitschriftenaufsatz
Publikationsdatum 18.10.2024
Sprache Englisch
Identifikator ISSN: 1083-6160, 1520-586X
KITopen-ID: 1000176044
Erschienen in Organic Process Research & Development
Verlag American Chemical Society (ACS)
Band 28
Heft 10
Seiten 3922–3928
Vorab online veröffentlicht am 24.09.2024
Nachgewiesen in Web of Science
Dimensions
Scopus
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