The chemistry of indoles. CVII. A novel synthesis of 3,4,5,6-tetrahydro-7-hydroxy-1H-azepino[5,4,3-cd]indoles and a new finding on Pictet-Spengler reaction.
Serotonins were found to produce 3,4,5,6-tetrahydro-7-hydroxy-1H-azepino[5,4,3-cd]indoles by simple heating with amines under an oxygen atmosphere. Serotonins also reacted with various aldehydes to provide 3,4,5,6-tetrahydro-7-hydroxy-1H-azepino[5,4,3-cd]indoles rather than beta-carbolines under basic conditions. In these novel reactions, the presence of the 5-hydroxy group on the indole nucleus was suggested to be essential. Possible mechanisms are discussed.
Somei
M
M
Faculty of Pharmaceutical Sciences, Kanazawa University, Japan. somei@dbs.p.kanazawa-u.ac.jp
Teranishi
S
S
Yamada
K
K
Yamada
F
F
D000588:Amines / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D012701:Serotonin / Q000031:analogs & derivatives* / Q000737:chemistry
D000588:Amines; D007202:Indicators and Reagents; D007211:Indoles; D012701:Serotonin