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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.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

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.