Reaction of Aromatic N-Oxides with Dipolarophiles. VII. Effect of Aromaticity on 1,3-Dipolar Cycloaddition Reactivity of Substituted Pyridine N-Oxides and Preparation of Oxazolo [4,5-b] pyridine Derivatives

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概要

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• The 1,3-dipolar cycloaddition reactivity of pyridine N-oxides to phenyl isocyanate was calculated by the MINDO/3 MO method using the perturbation equation derived by Klopman and Salem. The calculation did not predict the low reactivity of acceptor substituted pyridine N-oxides. On the basis of the calculation data, the general 1,3-dipolar cycloaddition reactivity of pyridine N-oxides towards various phenyl isocyanates is discussed in terms of the concept of cyclic conjugation. The aromaticity of the pyridine N-oxide may play an important role in determination of the reactivity. In connection with the cycloaddition, the 1,5-sigmatropic rearrangement of the primary cycloadducts and the pyrolytic reaction behavior of the 2,3-dihydropyridine derivatives formed by a 1,5-sigmatropic shift from the primary adducts are discussed on the basis of the MINDO/3 calculation data.

• 公益社団法人日本薬学会の論文
• 1984-06-25

著者

• 松岡 俊和

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 末松 文博

  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

• 品田 稔

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 品田 稔

  Faculty Of Pharmaceutical Sciences Kumamoto University

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