Highly Selective Electrosynthesis of 1<i>H</i>-1-Hydroxyquinol-4-ones-Synthetic Access to Versatile Natural Antibiotics.

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.

SUBMITTER: Prenzel T 

PROVIDER: S-EPMC11494660 | biostudies-literature | 2024 Oct

REPOSITORIES: biostudies-literature