Octahydro-7 (1H)-quinolones. III. cis-trans Isomerization of Octahydro-7 (1H)-quinolone Analogues

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概要

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• The isomerization reaction of N-nonsubstituted (1 and 3), N-benzylated (4 and 5), and N-benzoylated octahydro-7 (1H)-quinolones (6 and 7) and decahydroquinoline-2,7-dione derivatives (8-15) was investigated under various acidic and basic conditions. Except for the N-benzoyl-7-ones (6 and 7), isomerization features were interpreted as the phenomenon associated both with the facility of the cis-isomers and the difficulty of the trans-ones in the retro-Michael ring opening to form amino enone intermediates and with predominance of the cis-ring junction over the trans-one in the subsequent recyclization of the intermediates. Isomerization of N-benzoyloctahydro-7 (1H)-quinolone resulted in the exclusive formation of the cis-ketone (6) and in the successful isolation of the intermediate (18). The contrasting feature was interpreted by assuming both the facile ring opening of the trans-ketone (7) possibly via a cyclic process (7') and the retarded recyclization of 18,due to a reduced nucleophilicity of the amido nitrogen, resulting in a failure in the formation of 7.

• 公益社団法人日本薬学会の論文
• 1978-02-25

著者

• 今西 武

  Faculty Of Pharmaceutical Sciences Osaka University

• 内田 秀治

  Faculty of Pharmaceutical Sciences, Osaka University

• 百瀬 雄章

  Faculty of Pharmaceutical Sciences, Kinki University

• 木下 昌彦

  Faculty Of Pharmaceutical Sciences Osaka University

• 内田 秀治

  Faculty Of Pharmaceutical Sciences Osaka University

• 細谷 恵津子

  Faculty of Pharmaceutical Sciences, Osaka University

• 百瀬 雄章

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 細谷 恵津子

  Faculty Of Pharmaceutical Sciences Osaka University

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