Studies on Diazabenzobicyclo [3.3.1] nonane System. VIII. Synthesis of 8,9-Dimethoxy-11-benzoyl-1,2,5,6-tetrahydro-2,6-imino-3-benzazocin-4 (3H)-one

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概要

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• A synthetic route of 8,9-dimethoxy-11-benzoyl-1,2,5,6-tetrahydro-2,6-imino-3-benzazocin-4 (3H)-one (IX-B) having a new ring system was described. 3-(3,4-Dimethoxyphenyl) alanine ethyl ester (I) was condensed with diethyl malonate followed by cyclization with phosphoryl chloride to give ethyl 1-carbethoxymethylene-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (III), which was reduced to ethyl 3-carbethoxy-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-acetate (IV). N-benzoyl derivative (V) of IV was cyclized by a Dieckmann condensation to a tricyclic β-ketoester (VI), which was derived to 7,8-dimethoxy-10-benzoyl-4,5-dihydro-1H-1,4-iminobenzocyclohepten-3 (2H)-one (VII) by treating with dil. HCl. A Beckmann rearrangement of the oxime (VIII) of VII gave 8,9-dimethoxy-11-benzoyl-1,2,5,6-tetrahydro-1,5-imino-3-benzazocin-4 (3H)-one (IX-A) and IX-B.

• 公益社団法人日本薬学会の論文
• 1968-02-25

著者

• 三橋 監物

  Faculty of Pharmaceutical Sciences, University of Toyama

• 塩谷 俊作

  Faculty of Pharmaceutical Sciences, University of Toyama

• 堀 孝子

  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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