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Synthesis of a fused N-bridged (3.3.1)nonadiquinoline multicyclic skeleton via a metal-free formal (4 + 2) cycloaddition/Mannich/dearomatization domino reaction

We present a novel green synthetic protocol for the construction of a broad range of substituted fused azabicyclo[3.3.1]nonadiquinoline scaffolds through a formic acid catalyzed formal [4 + 2] annulation/Mannich/dearomatization domino reaction. This unified strategy shows a broad substrate scope wit...

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Main Authors: Amiri, Kamran (Author) , Nayebzadeh, Behrouz (Author) , Kamangar, Mohammad (Author) , Babazadeh, Mohammad (Author) , Ariafard, Alireza (Author) , Shiri, Farshad (Author) , Rominger, Frank (Author) , Balalaie, Saeed (Author)
Format: Article (Journal)
Language:English
Published: 29 Sep 2023
In: Green chemistry
Year: 2023, Volume: 25, Issue: 22, Pages: 9203-9208
ISSN:1463-9270
DOI:10.1039/D3GC03026A
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1039/D3GC03026A
Verlag, lizenzpflichtig, Volltext: https://pubs.rsc.org/en/content/articlelanding/2023/gc/d3gc03026a
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Author Notes:Kamran Amiri, Behrouz Nayebzadeh, Mohammad Kamangar, Mohammad Babazadeh, Alireza Ariafard, Farshad Shiri, Frank Rominger and Saeed Balalaie
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Summary:We present a novel green synthetic protocol for the construction of a broad range of substituted fused azabicyclo[3.3.1]nonadiquinoline scaffolds through a formic acid catalyzed formal [4 + 2] annulation/Mannich/dearomatization domino reaction. This unified strategy shows a broad substrate scope with high functional group tolerance, resulting in good to high yields under environmentally benign, transition-metal-free, low-cost, and operationally simple conditions. The current method outperforms existing methods in terms of green and sustainable conditions. The reaction mechanism was confirmed based on DFT calculations.
Item Description:Online veröffentlicht: 29. September 2023
Gesehen am 04.01.2024
Der Ausdruck "3.3.1" sowie der Ausdruck "4 + 2" sind im Titel eckig geklammert
Physical Description:Online Resource
ISSN:1463-9270
DOI:10.1039/D3GC03026A

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