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Regioselective Conjugate Addition of Nitriles to α,β‐Unsaturated Imines: Synthesis of Fluorinated Primary Enamines and 2‐Aminopyridine Derivatives
Author(s) -
Fernández de Trocóniz Guillermo,
Ochoa de Retana Ana M.,
Pascual Sergio,
Ezpeleta José M.,
Palacios Francisco
Publication year - 2013
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.201300580
Subject(s) - chemistry , regioselectivity , carbanion , malononitrile , aminopyridines , primary (astronomy) , intramolecular force , michael reaction , medicinal chemistry , organic chemistry , addition reaction , catalysis , physics , astronomy
Abstract The regioselective Michael addition of the carbanion of 2‐phenylacetonitrile (R 2 = Ph) and malononitrile (R 2 = CN) to fluoroalkylated α,β‐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).