Copper-Catalyzed [5 + 1] Annulation of 2-Ethynylanilines with an N,O-Acetal Leading to Construction of Quinoline Derivatives

Copper-Catalyzed [5 + 1] Annulation of 2-Ethynylanilines with an N,O-Acetal Leading to Construction of Quinoline Derivatives

A novel copper-catalyzed [5 + 1] annulation of 2-ethynylanilines with an N,O-acetal, which functioned as a C1 part, leading to the preparation of quinoline derivatives with an ester substituent on the 2-position is described. A combination of CuBr2 and trifluoroacetic acid (TFA) promoting [5 + 1] an...

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Veröffentlicht in:Organic letters 2012-02, Vol.14 (3), p.836-839
Hauptverfasser: Sakai, Norio, Tamura, Kosuke, Shimamura, Kazuyori, Ikeda, Reiko, Konakahara, Takeo
Format: Artikel
Sprache:eng
Schlagworte:
Acetals - chemistry
Acetylene - analogs & derivatives
Acetylene - chemistry
Aniline Compounds - chemistry
Catalysis
Copper - chemistry
Cyclization
Glyoxylates - chemistry
Molecular Structure
Nitrogen - chemistry
Oxygen - chemistry
Quinolines - chemistry
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Zusammenfassung:A novel copper-catalyzed [5 + 1] annulation of 2-ethynylanilines with an N,O-acetal, which functioned as a C1 part, leading to the preparation of quinoline derivatives with an ester substituent on the 2-position is described. A combination of CuBr2 and trifluoroacetic acid (TFA) promoting [5 + 1] annulation of the 2-ethynylaniline with ethyl glyoxylate is also demonstrated.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol203360g