Tandem β-Enamino Ester Formation and Cyclization with o-Alkynyl Anilines Catalyzed by InBr3: Efficient Synthesis of β-(N-Indolyl)-α,β-unsaturated Esters

Tandem β-Enamino Ester Formation and Cyclization with o-Alkynyl Anilines Catalyzed by InBr3: Efficient Synthesis of β-(N-Indolyl)-α,β-unsaturated Esters

A tandem reaction providing β-(N-indolyl)-α,β-unsaturated esters from β-keto esters and o-alkynyl anilines was developed. Z-Alkenes were selectively formed due to the stability of the β-enamino ester as an intermediate of the reaction. This reaction includes the intermolecular β-enamino ester format...

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Veröffentlicht in:Journal of organic chemistry 2009-02, Vol.74 (3), p.1418-1421
Hauptverfasser: Murai, Kenichi, Hayashi, Shoko, Takaichi, Nobuhiro, Kita, Yasuyuki, Fujioka, Hiromichi
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Aniline Compounds - chemistry
Chemistry
Cyclization
Esters - chemical synthesis
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Indoles - chemical synthesis
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
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Zusammenfassung:A tandem reaction providing β-(N-indolyl)-α,β-unsaturated esters from β-keto esters and o-alkynyl anilines was developed. Z-Alkenes were selectively formed due to the stability of the β-enamino ester as an intermediate of the reaction. This reaction includes the intermolecular β-enamino ester formation and intramolecular cyclization catalyzed by InBr3.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo802435b