Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 25, Pages 5614-5620Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300580
Keywords
Nitrogen heterocycles; Michael addition; Fluorine; Carbanions; Regioselectivity; Imines
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Funding
- Direccion General de Investigacion del Ministerio de Ciencia y Tecnologia (MICINN), Madrid DGI [CTQ2012-34.323]
- Gobierno Vasco
- University of the Basque Country UPV [GV7EJ, IT 422-10, UPV/EHU, UFI-QOSYC 11/12]
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The regioselective Michael addition of the carbanion of 2-phenylacetonitrile (R-2 = Ph) and malononitrile (R-2 = CN) to fluoroalkylated ,-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).
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