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1-1-羟基喹诺酮-4-酮的高选择性电合成——通往多功能天然抗生素的合成途径

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

作者信息

Prenzel Tobias, Schwarz Nils, Hammes Jasmin, Krähe Franziska, Pschierer Sarah, Winter Johannes, Gálvez-Vázquez María de Jesús, Schollmeyer Dieter, Waldvogel Siegfried R

机构信息

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.

出版信息

Org Process Res Dev. 2024 Sep 24;28(10):3922-3928. doi: 10.1021/acs.oprd.4c00337. eCollection 2024 Oct 18.

Abstract

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.

摘要

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。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a41/11494660/3128a1e676c3/op4c00337_0001.jpg

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