Dioxopyrrolines. XLVII. : Thermal Rearrangements of 7-Vinyl Derivatives of 1-Aryl-5-ethoxy-carbonyl-2-azabicyclo[3.2.0]heptane-3,4-diones and Their Imidates

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概要

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• Thermolysis of the 7-vinyl derivative of 1-aryl-5-ethoxycarbonyl-2-azabicyclo[3.2.0]heptane-3,4-dione caused two different types of skeletal rearrangement depending on the stereochemistry of the 7-vinyl group. The exo-isomer (2) gave the hydroindole (4) by the 1,3-shift of a C_1-C_7 bond to the vinyl group (path A reaction), while the endo-isomer (3) gave the 7-azabicyclo[4.2.1]nonane (5) by the Cope rearrangement (path B reaction). The product on thermolysis of the corresponding imidate also depends on the stereochemistry of the 7-vinyl group. The endo-isomer (13) gave the Cope product (12), while the exo-isomer (14) gave the dihydropyridone (16), which is produced by the 1,3-shift of the C_1-C_7 bond to the C_3 position followed by cheletropic loss of CO from the intermediary 2-azanorbornene (path C reaction). The validity of path C was proved by isolation of the 2-azanorbornenes (21 and 22) formed by thermolysis of the 7-vinyl-4-acetoxy imidate (20).

• 公益社団法人日本薬学会の論文
• 1990-05-25

著者

• 津田 喜典

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 津田 喜典

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 佐野 武弘

  Showa College of Pharmaceutical Sciences.

• 堀口 よし江

  昭和薬大

• 多賀 淳一

  Showa College of Pharmaceutical Sciences

• 津田 喜典

  金沢大薬

• 戸田 潤

  Showa College of Pharmaceutical Sciences

• 堀口 よし江

  Showa College of Pharmaceutical Sciences

• 田中 和彦

  Showa College Of Pharmaceutical Sciences

• 戸田 潤

  昭和薬科大学

• 神戸 末孝

  Showa College of Pharmaceutical Sciences

• 佐野 武弘

  Showa Pharmaceutical Univ. Tokyo Jpn

• 佐野 武弘

  Showa College Of Pharmaceutical Sciences

• 堀口 よし江

  Showa College Of Pharmaceutical Sciences University Of Kanazawa

• 多賀 淳一

  Showa College Of Pharmaceutical Sciences:kanazawa University

• 堀口 よしえ

  昭和薬科大学医療薬学教育研究センター

• 堀口 よし江

  昭和薬科大学医療薬学教育研究センター

• 戸田 潤

  昭和薬科大学医療薬学教育研究センター

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