Domino Transformations of gem-Trifluoroacetyl(bromo)alkenes under the Action of Secondary Amines

2‐Bromo‐3‐arylpropenyl trifluoromethyl ketones underwent aza‐Michael/hydroxyalkylation domino reactions triggered by secondary amines to give unexpectedly 2‐amino‐1‐trifluoromethyl indenols in good yields. The process was found to involve the intermediate formation of captodative aminoalkenes. Treat...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2007-12, Vol.2007 (36), p.6039-6045
Main Authors: Rulev, Alexander Yu, Uchakov, Igor A., Nenajdenko, Valentin G., Balenkova, Elisabeth S., Voronkov, Mikhail G.
Format: Article
Language:English
Subjects:
Domino reactions
Enones
Nucleophilic substitution
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Summary:2‐Bromo‐3‐arylpropenyl trifluoromethyl ketones underwent aza‐Michael/hydroxyalkylation domino reactions triggered by secondary amines to give unexpectedly 2‐amino‐1‐trifluoromethyl indenols in good yields. The process was found to involve the intermediate formation of captodative aminoalkenes. Treatment of 2‐bromo‐3‐thienyl derivatives with the same nucleophiles afforded the captodative trifluoroacetyl(amino)alkenes. The indenols obtained in this reaction can be converted into the corresponding indanones by acid hydrolysis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200700606