Facile synthesis of 1,2,3,4-tetrahydro-beta-carbolines by one-pot domino three-component indole formation and nucleophilic cyclization.
Two direct synthetic methods of 1,2,3,4-tetrahydro-beta-carboline derivatives have been developed. After initial indole formation by copper-catalyzed domino three-component coupling-cyclization using an appropriate ethynylaniline, aldehyde, and a secondary amine, treatment with t-BuOK/hexane or MsOH afforded the desired tetrahydro-beta-carboline derivatives in moderate to good yields.
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Yusuke
Y
Ohta
Shinya
S
Oishi
Nobutaka
N
Fujii
Hiroaki
H
Ohno
D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D002243:Carbolines; D007211:Indoles; C009804:tryptoline; D003300:Copper