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A Straightforward Entry to 7‐Azabicyclo[2.2.1]heptane‐1‐carbonitriles in the Synthesis of Novel Epibatidine Analogues
Author(s) -
Heugebaert Thomas,
Van Hevele Joke,
Couck Wouter,
Bruggeman Vicky,
Van der Jeught Sarah,
Masschelein Kurt,
Stevens Christian V.
Publication year - 2010
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.200901277
Subject(s) - epibatidine , chemistry , bicyclic molecule , heptane , nitrile , octane , imine , cyclohexanone , organic chemistry , stereochemistry , combinatorial chemistry , biochemistry , receptor , nicotinic agonist , nicotinic acetylcholine receptor , catalysis
This paper presents the synthesis of epibatidine analogues by a straightforward one‐pot method for the synthesis of 7‐azabicyclo[2.2.1]heptane‐1‐carbonitriles, starting from cyclohexanones bearing a leaving group at the 4‐position. In situ imine formation, followed by reversible cyanide addition, allows complete conversion of 4‐(mesyloxy)cyclohexanone to the bicyclic core. Elaboration of the introduced nitrile functionality and deprotection of the tertiary amine leads to five new epibatidine analogues.