Octahydro-7 (1H)-quinolones. IV. Construction of Decahydro-3H, 10H-benzo [i, j] quinolizine-3,10-dione Systems from cis-and trans-Octahydro-7 (1H)-quinolone

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概要

• 論文の詳細を見る

• The cyclization of N-acrylyl-trans-and-cis-octahydro-7 (1H)-quinolones (IXa and IXb) was examined under both acidic and basic conditions. Under kinetic conditions, the trans-isomer (IXa) gave two isomeric tricyclic lactams (X and XI) while the cis-isomer (IXb) gave no cyclized compounds. Under thermodynamic conditions, the cis-isomer (IXb) as well as the trans-isomer (IXa) gave the same lactams (X and XI). In the former case with kinetic conditions, the difference in behavior toward cyclization between IXa and IXb was interpreted by taking a stereoelectronic requirement for the Michael addition into consideration, and in the latter case with thermodynamic ones, unexpected formation of the lactams (X and XI) from the cis-isomer (IXb) was rationalized by assuming a reaction pathway via the intermediate enone (XXII) of which we succeeded in isolation from the reaction mixture.

• 公益社団法人日本薬学会の論文
• 1978-03-25

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

• 内田 秀治

  Faculty Of Pharmaceutical Sciences Osaka University

• 百瀬 雄章

  Faculty Of Pharmaceutical Sciences Kanazawa University

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