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Abstract <p>Azirinyl ethynyl ketones, containing aryl/<i>n-</i>alkyl substituents at azirine C<sup>2</sup>/C<sup>3</sup> and aryl/<i>n-</i>alkyl/2-thienyl substituents at the C≡C triple bond, undergo isomerization into 5-alkynyloxazoles under nucleophilic assistance in MeOH–K<sub>2</sub>CO<sub>3</sub> media at room temperature, with the formation of 5-alkynyloxazoles in 20–84% yield. According to DFT calculations, the addition of the methoxide anion nucleophile to the C=N bond of azirine promotes the opening of the three-membered ring across the C–C bond. The subsequent 5-<i>endo</i>-<i>trig</i> cyclization of formed 2-azabuta-1,3-dien-4-olate and aromatization results in the formation of the alkynyloxazole derivative.</p>

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Azirine-Based Synthesis of Fully Substituted 5-Alkynyloxazoles

  • 期刊论文

  • 发表日期：

    2026年2月9日

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  • Artur E. Taishev,
  • Ekaterina E. Galenko,
  • Mikhail S. Novikov,
  • Alexander F. Khlebnikov

摘要

Abstract

Azirinyl ethynyl ketones, containing aryl/n-alkyl substituents at azirine C2/C3 and aryl/n-alkyl/2-thienyl substituents at the C≡C triple bond, undergo isomerization into 5-alkynyloxazoles under nucleophilic assistance in MeOH–K2CO3 media at room temperature, with the formation of 5-alkynyloxazoles in 20–84% yield. According to DFT calculations, the addition of the methoxide anion nucleophile to the C=N bond of azirine promotes the opening of the three-membered ring across the C–C bond. The subsequent 5-endo-trig cyclization of formed 2-azabuta-1,3-dien-4-olate and aromatization results in the formation of the alkynyloxazole derivative.