Gold-Catalyzed Cascade Cyclization of (Azido)ynamides: An Efficient Strategy for the Construction of Indoloquinolines

Gold-Catalyzed Cascade Cyclization of (Azido)ynamides: An Efficient Strategy for the Construction of Indoloquinolines

(Azido)ynamides were efficiently converted into indoloquinolines by the use of a gold catalyst. While ynamides bearing an allylsilane gave terminal alkenes, ynamides bearing a simple alkene gave cyclopropanes. This reaction proceeds through the formation of an α-amidino gold carbenoid.

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Veröffentlicht in:Organic letters 2014-06, Vol.16 (11), p.3138-3141
Hauptverfasser: Tokimizu, Yusuke, Oishi, Shinya, Fujii, Nobutaka, Ohno, Hiroaki
Format: Artikel
Sprache:eng
Schlagworte:
Alkenes - chemistry
Azides - chemistry
Catalysis
Cyclization
Cyclopropanes - chemistry
Gold
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Molecular Structure
Quinolines - chemical synthesis
Quinolines - chemistry
Silanes - chemistry
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Zusammenfassung:(Azido)ynamides were efficiently converted into indoloquinolines by the use of a gold catalyst. While ynamides bearing an allylsilane gave terminal alkenes, ynamides bearing a simple alkene gave cyclopropanes. This reaction proceeds through the formation of an α-amidino gold carbenoid.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5012604