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Easy access to functionalized indolines and tetrahydroquinolines via a photochemical cascade cyclization reaction

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 off...

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Main Authors: Melder, Julian J. (Author) , Heldner, Maxi L. (Author) , Kugler, Robin (Author) , Ziegenhagen, Levi A. (Author) , Rominger, Frank (Author) , Rudolph, Matthias (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: May 14, 2024
In: Journal of the American Chemical Society
Year: 2024, Volume: 146, Issue: 21, Pages: 14521-14527
ISSN:1520-5126
DOI:10.1021/jacs.4c00962
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/jacs.4c00962
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Author Notes:Julian J. Melder, Maxi L. Heldner, Robin Kugler, Levi A. Ziegenhagen, Frank Rominger, Matthias Rudolph, and A. Stephen K. Hashmi
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Summary: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%.
Item Description:Gesehen am 04.11.2024
Physical Description:Online Resource
ISSN:1520-5126
DOI:10.1021/jacs.4c00962

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