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Communication | Regular issue | Vol 48, No. 6, 1998, pp.1117-1120
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8156
Syntheses of 1-Hydroxytryptamines and Serotonins Having Fattyacyl or (E)-3-Phenylpropenoyl Derivatives as an Nb-Substituent, and a Novel Homologation on the 3-Substituent of the 1-Hydroxytryptamines upon Treatment with Diazomethane

Masanori Somei,* Harunobu Morikawa, Koji Yamada, and Fumio Yamada

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan

Abstract

1-Hydorxytryptamines (6a-f) having (E)-3-phenyl-, (E)-3-(4-hydroxyphenyl)-, (E)-3-(4-hydroxy-3-methoxyphenyl)propenoyl, octanoyl, hexadecanoyl, and docosanoyl group as a Nb-substituent are prepared for the first time. Preparations of serotonins (2a-c, e) from the corresponding 1-hydroxytryptamines (6a-c, e) are also reported. A novel homologation on the 3-substituent of 1-hydroxytryptamines is discovered upon treatment with diazomethane in chloroform or dichloromethane.