1,6-Dihydro-3 (2H)-pyridinones. II. Synthesis of 2-Azabicyclo [2. 2. 2] octanes by the Reaction of N-Substituted 1,6-Dihydro-3 (2H)-pyridinones with 1,3-Dicarbonyl Compounds

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概要

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• Base-catalyzed reaction of N-substituted 1,6-dihydro-3 (2H)-pyridinones (1 and 2) with some 1,3-dicarbonyl compounds (8a-e) resulted in exclusive formation of the 2-azabicyclo [2. 2. 2] octan-7-ones (5 and 6), while a similar treatment of 1 with dimethyl acetonedicarboxylate (8f) gave the 3-azabicyclo [3. 3. 1] nonan-7-one (10f) as a sole product. On deethoxycarbonylation under acidic conditions, the azabicyclooctanecarboxylates (5a, 5c, 6a, and 6c) afforded the 3-azabicyclo [3. 3. 1] nonanes (13 and 16) and/or the 2-azabicyclo [2. 2. 2] octanes (14,15,17,and 18). On the other hand, ketalization of a mixture of 17 and 18 with ethylene glycol provided the diketal (23), which was derived into the monoketone (24) upon treatment with 98% formic acid. Haloform reaction of 24 followed by esterification yielded the ester (26), which was transformed into the aldehyde (28) by sodium borohydride reduction and subsequent PCC oxidation. An acidic hydrolysis of 28 directly furnished the desired 2-azabicyclo [2. 2. 2] octanone derivative (7), a possible synthon for the Iboga alkaloids.

• 社団法人日本薬学会の論文
• 1982-11-25

著者

• 今西 武

  Faculty Of Pharmaceutical Sciences Osaka University

• 花岡 美代次

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 百瀬 雄章

  Faculty of Pharmaceutical Sciences, Kinki University

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Osaka University

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 新 広昭

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 今西 一郎

  Faculty of Pharmaceutical Sciences, Osaka University

• 百瀬 雄章

  (present Address)faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 新 広昭

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 今西 一郎

  Faculty Of Pharmaceutical Sciences Osaka University

• 百瀬 雄章

  Faculty Of Pharmaceutical Sciences Kanazawa University

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