Regioselective Conjugate Addition of Nitriles to [alpha],[beta]-Unsaturated Imines: Synthesis of Fluorinated Primary Enamines and 2-Aminopyridine Derivatives

The regioselective Michael addition of the carbanion of 2-phenylacetonitrile (R2 = Ph) and malononitrile (R2 = CN) to fluoroalkylated [alpha],[beta]-unsaturated imines 1 is described. Fluorinated imines 1 were used as intermediates for the regioselective 1,4-addition and synthesis of functionalized...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-09, Vol.2013 (25), p.5614
Main Authors: Fernandez de Troconiz, Guillermo, Ochoa de Retana, Ana M, Pascual, Sergio, Ezpeleta, José M, Palacios, Francisco
Format: Article
Language:English
Subjects:
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Summary:The regioselective Michael addition of the carbanion of 2-phenylacetonitrile (R2 = Ph) and malononitrile (R2 = CN) to fluoroalkylated [alpha],[beta]-unsaturated imines 1 is described. Fluorinated imines 1 were used as intermediates for the regioselective 1,4-addition and synthesis of functionalized fluorinated primary enamines 5 and 7, fluorine-containing trans-3,4-dihydro-2-aminopyridines 2, and fluorinated 2-aminopyridines 4 and 8, which were obtained with total atom economy. Derivatives 2 and 8 were also prepared by an intramolecular cyclocondensation reaction of functionalized fluorinated primary enamines 5 and 7, respectively, in the presence of a base (NaH). [PUBLICATION ABSTRACT]
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201300580