Convenient synthesis of melatonin analogues: 2- and 3-substituted - N-acetylindolylalkylamines

A new method for the synthesis of 2- and 3-substituted indolylalkylamides, derivatives of melatonin, from arylhydrazines and amidoketones by the Fischer reaction was elaborated. The amidoketones can be easily prepared from cyclic imines by reaction with acylpyridinium chloride. This method is a one-...

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Bibliographic Details
Published in:Tetrahedron 2004-12, Vol.60 (51), p.11719-11724
Main Authors: Nenajdenko, Valentine G., Zakurdaev, Eugene P., Prusov, Eugene V., Balenkova, Elizabeth S.
Format: Article
Language:English
Subjects:
Amidoketones
Arylhydrazines
Cyclic imines
Fischer reaction
Indoles
Melatonin
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Summary:A new method for the synthesis of 2- and 3-substituted indolylalkylamides, derivatives of melatonin, from arylhydrazines and amidoketones by the Fischer reaction was elaborated. The amidoketones can be easily prepared from cyclic imines by reaction with acylpyridinium chloride. This method is a one-step synchronous creation of the selected alkylamide fragment and the indole core. Variation of the arylhydrazines create the desired substituents in the carbocycle of indolylalkylamides and suitable choice of amidoketone can direct the amidoalkyl chain to the 2- or 3-position of the indole. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.10.006