A Straightforward Entry to 7-Azabicyclo[2.2.1]heptane-1-carbonitriles in the Synthesis of Novel Epibatidine Analogues

摘要

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 cyclo-hexanones 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.