Dioxopyrrolines. XLIV. : Thermal 1,3-Shift of 2-Azabicyclo[3.2.0]hept-2-ene Ring System : A New Entry to 3,4-Dihydropyridines and 2-Azanorborn-2-enes

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概要

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• Thermolysis of 4-oxo-2-azabicyclo[3.2.0]hept-2-enes caused two reactions; one is the 1,3-shift of the C_1-C_7 bond to the C_3 carbon followed by cheletropic loss of CO from the intermediary formed 2-azanorborn-2-enes to yield the dihydropyridines, and the other is epimerization of the C_7-substituent. These two reactions occurred competitively depending on the nature of the C_7 substituent. Intermediary formation of the 2-azanorborn-2-enes in the rearrangement reaction was proved by trapping experiments with the use of 4-acetoxy derivatives. The mechanisms of the thermal 1,3-shift and 7-epimerization are discussed.

• 公益社団法人日本薬学会の論文
• 1990-01-25

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

• 津田 喜典

  金沢大薬

• 堀口 よし江

  Showa College of Pharmaceutical Sciences

• 田中 和彦

  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

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