Gold(III)-catalyzed site-selective and divergent synthesis of 2-Aminopyrroles and Quinoline-based Polyazaheterocycles

A facile, site-selective, and divergent approach to construct 2-aminopyrroles and quinoline-fused polyazaheterocycles enabled by a simple gold(III) catalyst from ynamides and anthranils under mild reaction conditions is described. This one-pot strategy uses readily available starting materials, proc...

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Hauptverfasser: Zeng, Zhongyi (VerfasserIn) , Jin, Hongming (VerfasserIn) , Rudolph, Matthias (VerfasserIn) , Rominger, Frank (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: December 10, 2018
In: Angewandte Chemie. International edition
Year: 2018, Jahrgang: 57, Heft: 50, Pages: 16549-16553
ISSN:1521-3773
DOI:10.1002/anie.201810369
Online-Zugang:Resolving-System, Volltext: http://dx.doi.org/10.1002/anie.201810369
Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201810369
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Verfasserangaben:Zhongyi Zeng, Hongming Jin, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
Beschreibung
Zusammenfassung:A facile, site-selective, and divergent approach to construct 2-aminopyrroles and quinoline-fused polyazaheterocycles enabled by a simple gold(III) catalyst from ynamides and anthranils under mild reaction conditions is described. This one-pot strategy uses readily available starting materials, proceeds in a highly step- and atom-economical manner, with broad substrate scope and scale-up potential. The key element for success in this tandem reaction is a catalyst-directed preferred quenching of the in situ generated gold carbene intermediates by a nucleophilic benzyl/2-furylmethyl moiety on the ynamides as an alternative to the known C−H annulation leading to indoles.
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Gesehen am 11.12.2018
Beschreibung:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.201810369