Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1315315 | Journal of Fluorine Chemistry | 2006 | 5 Pages |
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.
Graphical abstract7-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 were converted to the corresponding serotonins. The melatonins were prepared by a one-pot reaction that involved in situ acetylation of the aminobutyraldehyde. Figure optionsDownload full-size imageDownload as PowerPoint slide