Domino Heck-aza-Michael reactions: efficient access to 1-substituted tetrahydro-beta-carbolines.
A simple and efficient palladium-catalyzed domino reaction for the synthesis of a series of C1-substituted tetrahydro-beta-carbolines is described. This domino process involves a Heck reaction at the indole 2-position of a halogenated tryptamine precursor, followed by intramolecular aza-Michael addition.
School of Life and Environmental Science, Deakin University, Geelong 3217, Victoria, Australia.
Daniel L
DL
Priebbenow
Luke C
LC
Henderson
Frederick M
FM
Pfeffer
Scott G
SG
Stewart
D001372:Aza Compounds / Q000737:chemistry*; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D014363:Tryptamines / Q000737:chemistry*
D001372:Aza Compounds; D002243:Carbolines; D014363:Tryptamines; D010165:Palladium