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| Verfasst von: | Melder, Julian J. [VerfasserIn]  |
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| | Heldner, Maxi L. [VerfasserIn] |
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| | Kugler, Robin [VerfasserIn] |
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| | Ziegenhagen, Levi A. [VerfasserIn] |
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| | Rominger, Frank [VerfasserIn] |
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| | Rudolph, Matthias [VerfasserIn] |
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| | Hashmi, A. Stephen K. [VerfasserIn] |
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| Titel: | Easy access to functionalized indolines and tetrahydroquinolines via a photochemical cascade cyclization reaction |
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| Verf.angabe: | Julian J. Melder, Maxi L. Heldner, Robin Kugler, Levi A. Ziegenhagen, Frank Rominger, Matthias Rudolph, and A. Stephen K. Hashmi |
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| E-Jahr: | 2024 |
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| Jahr: | May 14, 2024 |
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| Umfang: | 7 S. |
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| Illustrationen: | Illustrationen |
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| Fussnoten: | Gesehen am 04.11.2024 |
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| Titel Quelle: | Enthalten in: American Chemical SocietyJournal of the American Chemical Society |
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| Ort Quelle: | Washington, DC : ACS Publications, 1879 |
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| Jahr Quelle: | 2024 |
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| Band/Heft Quelle: | 146(2024), 21 vom: Mai, Seite 14521-14527 |
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| ISSN Quelle: | 1520-5126 |
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| Abstract: | Herein, the development of a light-mediated synthesis of functionalized indolines and tetrahydroquinolines is reported. These structural motifs are considered as highly valuable targets, attributed to their widespread occurrence in pharmaceuticals and natural products. The gold-mediated approach offers a direct route to functionalized indolines in yields of up to 81% under mild photochemical conditions. Thereby, easily accessible Boc-protected N-aryl-allylamine and homoallylamine derivatives were reacted with sp3-hybridized haloalkanes in an intermolecular cascade cyclization reaction. A broad scope of substrates, including a variety of different substituents on the aromatic backbone as well as various haloalkanes, could be utilized. Indoline derivatives, which are functionalized in position 2, are also accessible by applying ortho-allylic anilines. Moreover, the synthetic appeal was demonstrated for a total synthesis of the anti-inflammatory agent AN669 in three reaction steps in an overall yield of 64%. |
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| DOI: | doi:10.1021/jacs.4c00962 |
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| URL: | Bitte beachten Sie: Dies ist ein Bibliographieeintrag. Ein Volltextzugriff für Mitglieder der Universität besteht hier nur, falls für die entsprechende Zeitschrift/den entsprechenden Sammelband ein Abonnement besteht oder es sich um einen OpenAccess-Titel handelt.
Volltext: https://doi.org/10.1021/jacs.4c00962 |
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| | DOI: https://doi.org/10.1021/jacs.4c00962 |
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| Datenträger: | Online-Ressource |
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| Sprache: | eng |
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| K10plus-PPN: | 1907695540 |
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| Verknüpfungen: | → Zeitschrift |
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Easy access to functionalized indolines and tetrahydroquinolines via a photochemical cascade cyclization reaction / Melder, Julian J. [VerfasserIn]; May 14, 2024 (Online-Ressource)
