Synthesis of bridged bicyclic hydrazines via endocyclic N-acylhydrazonium intermediates: A novel route to the 1-azatropane skeleton

Article abstract of DOI:10.1016/S0040-4020(01)80199-X

Bicyclic molecules with the 1,7-diaza-6,6-dimethylbicyclo[2.2.1]heptane and 1,8-diaza-7,7-dimethylbicyclo[3.2.1]octane (1-aza-7,7-dimethytropane) skeleton are shown to be efficiently synthesized via cyclization reactions of endocyclic N-acylhydrazonium intermediates. By using a protected β-ketoester as the internal nucleophile, azacocaine analogues are also accessible via this methodology.