Tandem beta-enamino ester formation and cyclization with o-alkynyl anilines catalyzed by InBr3: efficient synthesis of beta-(N-indolyl)-alpha,beta-unsaturated esters

Kenichi Murai; Shoko Hayashi; Nobuhiro Takaichi; Yasuyuki Kita; Hiromichi Fujioka

doi:10.1021/jo802435b

Tandem beta-enamino ester formation and cyclization with o-alkynyl anilines catalyzed by InBr3: efficient synthesis of beta-(N-indolyl)-alpha,beta-unsaturated esters

J Org Chem. 2009 Feb 6;74(3):1418-21. doi: 10.1021/jo802435b.

Authors

Kenichi Murai¹, Shoko Hayashi, Nobuhiro Takaichi, Yasuyuki Kita, Hiromichi Fujioka

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871 Japan.

PMID: 19113947
DOI: 10.1021/jo802435b

Abstract

A tandem reaction providing beta-(N-indolyl)-alpha,beta-unsaturated esters from beta-keto esters and o-alkynyl anilines was developed. Z-Alkenes were selectively formed due to the stability of the beta-enamino ester as an intermediate of the reaction. This reaction includes the intermolecular beta-enamino ester formation and intramolecular cyclization catalyzed by InBr(3).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Aniline Compounds / chemistry*
Cyclization
Esters / chemical synthesis*
Indoles / chemical synthesis*

Substances

Alkynes
Aniline Compounds
Esters
Indoles