Syntheses of functionalized 1,4-disubstituted gamma-carbolines.
We report the complete synthesis of a variety of 1,4-disubstituted gamma-carbolines. These compounds are of particular interest for their involvement in many biological processes and are believed to possess various medicinal activities. A large number of N-tosylaldimines were condensed with indoles affording an array of 3-aminomethyl indoles. Subsequent additions, followed by intramolecular cyclization, afforded an array of 1,2-dihydro-3H-gamma-carbolones in good yield. Upon subsequent aromatization, the corresponding fully aromatic functionalized 1-aryl-4-hydroxy-gamma-carbolines resulted.
Wynne
James H
JH
Department of Chemistry, George Mason University, Fairfax, VA 22030, USA.
Stalick
Wayne M
WM
D002243:Carbolines / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents; D007211:Indoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000737:chemistry
D002243:Carbolines; D007202:Indicators and Reagents; D007211:Indoles; D014105:Tosyl Compounds