Syntheses of 7-fluoro- and 6,7-difluoroserotonin and 7-fluoro- and 6,7-difluoromelatonin

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. © 2006 Elsevier B.V. All rights reserved.

Año de publicación:

2006

Keywords:

• Fischer indole synthesis
• melatonin
• Serotonin

Fuente:

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