Prenzel Tobias, Schwarz Nils, Hammes Jasmin, Krähe Franziska, Pschierer Sarah, Winter Johannes, Gálvez-Vázquez María de Jesús, Schollmeyer Dieter, Waldvogel Siegfried R
Department of Chemistry, Johannes Gutenberg University, Duesbergweg 10-14, 55128 Mainz, Germany.
Max-Planck-Institute for Chemical Energy Conversion, Stiftstraße 34-36, 45470 Mülheim an der Ruhr, Germany.
Org Process Res Dev. 2024 Sep 24;28(10):3922-3928. doi: 10.1021/acs.oprd.4c00337. eCollection 2024 Oct 18.
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.
1-1-羟基喹啉-4-酮代表了一类具有环外N,O基序的广泛的生物活性杂环化合物。电合成通过硝基还原提供了直接、高度选择性且可持续地获得1-羟基喹啉-4-酮的方法。建立了一条从易于获得的2-硝基苯甲酸出发的通用合成路线。该方案在26个实例中得到了证明,产率高达93%,天然存在的抗生素金霉素C和HQNO突出了其广泛适用性。多克规模的电解强调了该方法的实用性和技术相关性。