Journal
CHEMICAL & PHARMACEUTICAL BULLETIN
Volume 49, Issue 9, Pages 1159-1165Publisher
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.49.1159
Keywords
3,4,5,6-tetrahydro-7-hydroxy-1H-azepino[5,4,3-cd]indole; serotonin
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Serotonins were found to produce 3,4,5,6-tetrahydro-7-hydroxy-4H-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 fl-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.
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