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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概要

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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.

• 公益社団法人日本薬学会の論文
• 1966-04-25

著者

• 三橋 監物

  Faculty of Pharmaceutical Sciences, University of Toyama

• 塩谷 俊作

  Faculty of Pharmaceutical Sciences, University of Toyama

• 塩谷 俊作

  Toyama Technical College

• 三橋 監物

  Faculty Of Pharmaceutical Sciences Josai University

関連論文

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• Thiazole Analogs of Benzomorphans. II. Synthesis of Novel Thiazolo [5,4-f] morphans
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• On the Condensation Products of Nitromalondialdehyde with Ethylenediamine
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• On the Cleavage of Tertiary Amines with Ethyl Chloroformate
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