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Domino Transformations of gem‐ Trifluoroacetyl(bromo)alkenes under the Action of Secondary Amines
Author(s) -
Rulev Alexander Yu.,
Uchakov Igor A.,
Nenajdenko Valentin G.,
Balenkova Elisabeth S.,
Voronkov Mikhail G.
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700606
Subject(s) - chemistry , trifluoromethyl , domino , nucleophile , hydrolysis , organic chemistry , reaction conditions , medicinal chemistry , catalysis , alkyl
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)