[Synthesis, reactions, and CNS-actions of 6,7-annealed 8-oxatropane derivatives]

The butadiene derivatives 10a-c react with the oxa-bicyclooctanone 9 to give the cyclohexene annulated oxatropanes 11a-c. The acetoxyderivatives 11b and 11c can be transformed into the cyclohexadiene or benzene derivatives 13 and 12, respectively. 11a reacts with HN3 to afford the tricyclic oxazepanone 14 which can be reduced to give 15a; the oxime-tosylate 16b reacts with Al(CH3)3/DIBALH to yield the oxazepane 15c. Treatment of the oxabicyclooctanes 9 and 19 with benzonitrile oxide or diazomethane affords the isoxazoline or pyrazoline annulated oxatropanes 21, 22, and 20, respectively. 21 was reduced to the amino alcohol 23. 15c and 23 show CNS-activity in the mouse.