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DOI: 10.1055/a-2339-2832
Electrosynthesis of Quinoxalines via Intermolecular Cyclization/Dehydrogenation of Ketones with o-Phenylenediamines
Autoren
We are grateful for the financial support provided by the Science and Technology Planning Project of Qiqihar (LSFGG-2023025).
Abstract
In this study, we proposed a novel electrochemical dehydrogenative synthetic method for preparing 2-substituted quinoxalines by intermolecular cyclization of aryl alkyl ketones and o-phenylenediamines. This method gave various quinoxalines in yields ranging from 35% to 71%. This novel protocol employs mild reaction conditions and offers moderate to excellent yields, a wide substrate scope, and broad functional-group compatibility. Furthermore, a late-stage functionalization and the wide substrate scope demonstrated the synthetic utility of this protocol.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2339-2832.
- Supporting Information (PDF) (opens in new window)
Publikationsverlauf
Eingereicht: 15. Mai 2024
Angenommen nach Revision: 29. Mai 2024
Accepted Manuscript online:
05. Juni 2024
Artikel online veröffentlicht:
14. Juni 2024
© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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- 16 Quinoxalines 3aa–be; General Procedure A tube was charged with the appropriate ketone 1 (0.5 mmol, 1.0 equiv), amine 2 (0.75 mmol, 1.5 equiv), KI (0.25 mmol, 0.5 equiv), H2C2O4·2 H2O (0.5 mmol, 1.0 equiv), n Bu4NI (0.25 mmol, 0.5 equiv), and DMA (6 mL). The tube was then equipped with a graphite felt anode and a Pt foam cathode, and its contents were subjected to constant-current (15.0 mA) electrolysis at 100 °C for 24 h. After complete consumption of the starting material, the mixture was extracted with EtOAc, and the organic layer was dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (silica gel, EtOAc–hexane). 2-Phenylquinoxaline (3aa)17a Yellow solid; yield: 70 mg (68%). 1H NMR (600 MHz, CDCl3): δ = 9.33 (s, 1 H), 8.22–8.19 (m, 2 H), 8.15 (ddd, J = 22.2, 8.4, 1.8 Hz, 2 H), 7.77 (dddd, J = 23.4, 8.4, 7.2, 1.2 Hz, 2 H), 7.59–7.52 (m, 3 H). 13C NMR (150 MHz, CDCl3): δ = 152.2, 143.7, 142.7, 141.8, 137.1, 130.7, 130.6, 130.0, 129.9, 129.5, 129.4, 127.9. 2-(4-Bromophenyl)quinoxaline (3ak)17b Yellow solid; yield: 63 mg (44%). 1H NMR (600 MHz, CDCl3): δ = 9.27 (s, 1 H), 8.11 (ddd, J = 8.4, 6.4, 2.0 Hz, 2 H), 8.08–8.04 (m, 2 H), 7.80–7.72 (m, 2 H), 7.70–7.65 (m, 2 H). 13C NMR (150 MHz, CDCl3): δ = 150.4, 142.6, 142.0, 141.5, 135.4, 132.1, 130.3, 129.6, 129.4, 129.0, 128.8, 124.8.