Tandem beta-enamino ester formation and cyclization with o-alkynyl anilines catalyzed by InBr3: efficient synthesis of beta-(N-indolyl)-alpha,beta-unsaturated esters.
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).
Murai
Kenichi
K
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871 Japan.
Hayashi
Shoko
S
Takaichi
Nobuhiro
N
Kita
Yasuyuki
Y
Fujioka
Hiromichi
H
D000480:Alkynes / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D003500:Cyclization; D004952:Esters / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis*
D000480:Alkynes; D000814:Aniline Compounds; D004952:Esters; D007211:Indoles