Reaction of Aromatic N-Oxides with Dipolarophiles. XI. : 1,3-Dipolar Cycloaddition Reaction of Pyridine N-Oxides with Tosyl Isocyanate and One-Pot Synthesis of 2-Oxooxazolo-[4,5-b]pyridine Derivatives

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概要

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• The cycloaddition reactivity of tosyl isocyanate toward pyridine N-oxides was calculated by the CNDO/2 method using a perturbation equation, and the results indicated that the initial stage of the reaction might be controlled by the coulombic attraction. The 1,3-dipolar cycloaddition reaction of tosyl isocyanate with two equivalents of 3,5-dibromopyridine N-oxide in refluxing benzene gave 6-bromo-2-oxooxazolo[4,5-b]pyridine, while the use of one equivalent of 3,5-dichloropyridine N-oxide gave 6,7a-dichloro-2-oxo-3-tosyl-3a, 7a-dihydrooxazolo[4-, 5-b]pyridine, formed from the 1,5-sigmatropic rearrangement of the corresponding primary cycloadduct. When the reaction was carried out in the presence of triethylamine in benzene, 6-halogeno-2-oxo-3-tosyloxazolo[4,5-b]pyridine was isolated.The observed activation parameters, as well as the small solvent effects, may be interpreted in termas of a concerted pathway.The reaction should be very valuable as a one-pot synthesis of 2-oxooxazolo[4,5-b]pyridines, which are pyridine analogues of 5-chloro-2-benzoxazolinone.

• 公益社団法人日本薬学会の論文
• 1986-04-25

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

• 村岡 敬治

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 篠原 郁夫

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 福岡 竜逸

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 福岡 竜逸

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 村岡 敬治

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 篠原 郁夫

  Faculty Of Pharmaceutical Sciences Kumamoto University

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