Studies on Diazabenzobicyclo [3.3.1] nonane System. IV. Synthesis of 1, 2, 3, 4, 5, 6-Hexahydro-1, 5-methanobenzo [e] [1, 3] diazocine Derivatives

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In order to test the pharmacological activities, some derivatives of 1, 2, 3, 4, 5, 6-hexahydro-1, 5-methanobenzo [e] [1, 3] diazocine were synthesized.cis-1, 2, 3, 4-tetrahydro-1, 3-naphthalenediamine (V) was prepared by Schmidt reaction of cis-4-amino-1, 2, 3, 4-tetrahydro-2-naphthoic acid (IV) which was obtained by catalytic reduction of methyl 4-hydroximino-1, 2, 3, 4-tetrahydro-2-naphthoate (I), followed by cyclization and hydrolysis. Reduction of N, N′-diacetyl-(VIa) and N, N′-diformyl-(VIb) derivatives of V with lithium aluminum hydride afforded N, N′-diethyl-(VIIa) and N, N′-dimethyl-(VIIb) derivatives, respectively. Condensation of VIIa with formaldehyde and benzaldehyde gave 2, 4-diethyl-(VIIIa) and 2, 4-dimethyl-3-phenyl-1, 2, 3, 4, 5, 6-hexahydro-1, 5-methanobenzo [e] [1, 3]-diazocine (VIIIc). Similarly, 2, 4-dimethyl derivatives (VIIIb) and (VIIId) were prepared.

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