Stan V. D'Andrea

The synthesis of 9-(1-azetidinyl)-1,2,3,4-tetrahydroacridine

Synthesis of analogue (2) of tacrine is described in which the primary amino group is replaced by the azetidine moiety. The synthesis was accomplished in two steps from the acridinone derivative 10. This involved conversion of 10 to triflate 11, followed by treatment with azetidine to give the target compound 2

Anticonvulsants related to U-54494 prepared from cis-1,2- and cis-2,3- diaminotetralin

Abstract cis-Diaminotetralins 4 and 10 were converted in 4 steps to benzologs of the novel anticonvulsant U-54494. Attempted alkylation of 4 and 10 with 1,4-dibromobutane provided mixtures of the bis-pyrrolidino compounds and starting free bases together with the desired mono- pyrrolidino compounds 5 and 11. Treatment of these mixtures with ethyl chloroformate followed by Chromatographic separation gave the carbamates 7 and 12. Reduction of these carbamates with LiAlH4 provided the N-methylamino compounds 8 and 14. Finally, benzamide formation gave rise to the analogs of U-54494, compounds 9 and 15.