Synthesis of annulated gamma-carbolines by palladium-catalyzed intramolecular iminoannulation.
[reaction: see text] A variety of N-substituted 2-bromo-1H-indole-3-carboxaldehydes incorporating an alkyne-containing tether on the indole nitrogen have been converted to the corresponding tert-butylimines, which have been subjected to palladium-catalyzed intramolecular iminoannulation, affording various annulated gamma-carbolines in excellent yields.
Zhang
Haiming
H
Department of Chemistry, Iowa State University, Ames 50011, USA.
Larock
Richard C
RC
D000480:Alkynes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D002243:Carbolines / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D007097:Imines / Q000737:chemistry; D010165:Palladium / Q000737:chemistry
D000480:Alkynes; D000970:Antineoplastic Agents; D002243:Carbolines; D007097:Imines; D010165:Palladium