No abstract

Preparation of bridged benzoxadiazocines (III) and (VI) with substitution at N-5 is carried out with alkylating, acylating, or sulfonylating agents while preparation of analogues with variations in the benzo substituent, the bridgehead substituent, or the methano-bridge substituent involves preparation of the appropriate ketones (IX) and (XIV) and aldehydes. Bridged benzodiazocines like (XIX) are prepared by cyclization of appropriate cis naphthalene derivatives (XVII) with imidate (XVIII). The diamines are prepared by a literature method. The carbocyclic compounds are somewhat more insecticidally active than analogous oxacyclic compounds. exo-Orientation of the bridgehead methyl group leads to higher activity than endo-orientation. The new compounds inhibit AChE in a reversible manner, analogous to structurally related huperzine A. -(FINKELSTEIN, BRUCE L.; BENNER, ERIC A.; HENDRIXSON, MAURA C.; KRANIS, KEVIN T.; RAUH, JAMES J.; SETHURAMAN, MAYA R.; MCCANN, STEPHEN F.; Bioorg. Med. Chem.