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Syntheses of 7-fluoro- and 6,7-difluoroserotonin and 7-fluoro- and 6,7-difluoromelatonin
Authors:Jorge Heredia-Moya  Kenneth L Kirk
Institution:Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Department of Health and Human Services, Bethesda, MD 20892, United States
Abstract:The Abramovitch adaption of the Fischer indole synthesis gave low yields of 7-fluoro-5-methoxytryptamine due in part to decomposition during the required decarboxylation step. Therefore, 7-fluoro- and 6,7-difluoro-5-methoxytryptamines were prepared by reaction of aminobutyraldehyde (generated in situ from the diethyl acetal) with 2-fluoro- and 2,3-difluoro-4-methoxyphenylhydrazine, and the products converted to the corresponding serotonins. The melatonins were prepared by a one-pot reaction that involved in situ acetylation of the aminobutyraldehyde.
Keywords:Serotonin  Melatonin  Fischer indole synthesis
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