Reaction of Aromatic N-Oxides with Dipolarophiles. XIV. : Inverse-Type Cycloaddition of Pyridine N-Oxides with 1,4-Epoxy-1,4-dihydronaphthalene and Its Mechanistic Aspects

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概要

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• In connection with the stereoselective exo cycloaddition in the 1,3-dipolar reaction of 3,5-lutidine N-oxide and N-arylmaleimides, the inverse-type cycloaddition of some pryidine N-oxides with 1,4-epoxy-1,4-dihydronaphthalene was investigated. In these reactions, the armatized furopyridine-type compounds formed from the 1,5-sigmatropic rearrangement products of the primary cycloadducts were isolated. During the course of the reaction, coloration due to charge-transfer complex formation was observed. The reaction obeyed a second-order rate law and showed little solvent effect. The observed reactivity and stereochemistry are discussed in terms of frontier molecular orbital (FMO) considerations.

• 公益社団法人日本薬学会の論文
• 1990-03-25

著者

• 松岡 俊和

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 原野 一誠

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 久野 拓造

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 原野 一誠

  熊本大学 薬

• 原野 一誠

  熊本大学薬学部

• 久野 拓三

  熊本大学薬学部

• 鈴木 俊之

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 村山 康子

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 鈴木 俊之

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 村山 康子

  Faculty Of Pharmaceutical Sciences Kumamoto University

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