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Fischer Reaction with 2-Perfluoroalkylated Cyclic Imines - An Efficient Route to 2-Perfluoroalkyl-Substituted Tryptamines and Their Derivatives and Homologues

The reaction of 2‐perfluoroalkyl‐substituted cyclic imines with arylhydrazines was investigated. We found that 2‐perfluoroalkylated cyclic imines are highly reactive electrophiles that form, through ring opening, the corresponding hydrazones bearing an amine group at the end of the alkyl chain. Subs...

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Bibliographic Details
Published in:European journal of organic chemistry 2015-09, Vol.2015 (29), p.6479-6488
Main Authors: Shmatova, Olga I., Shevchenko, Nikolay E., Nenajdenko, Valentine G.
Format: Article
Language:English
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Summary:The reaction of 2‐perfluoroalkyl‐substituted cyclic imines with arylhydrazines was investigated. We found that 2‐perfluoroalkylated cyclic imines are highly reactive electrophiles that form, through ring opening, the corresponding hydrazones bearing an amine group at the end of the alkyl chain. Subsequent acidic treatment resulted in a Fischer rearrangement. Thus, a new synthesis of 2‐perfluoroalkylated tryptamines and their homologues through a Fischer reaction was developed. The possibility of modification of the indole core of the 2‐CF3‐substituted tryptamine products was demonstrated, and various 2‐trifluoromethylated tryptamines substituted at the 5‐position were prepared. An efficient method for the synthesis of CF3‐substituted tryptamines was developed based on the Fischer reaction of perfluoroalkyl‐substituted cyclic imines with arylhydrazines. A 5‐bromotryptamine was also transformed into further derivatives.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500860