A Facile Approach to the Synthesis of 3-Acylisoxazole Derivatives with Reusable Solid Acid Catalysts

Ken-ichi Itoh*, Mamiko Hayakawa, Rina Abe, Shinji Takahashi, Kenta Hasegawa, Tadashi Aoyama

*Department of Liberal Arts and Science, College of Science and Technology, Nihon University, 7-24-1, Narashinodai, Funabashi-shi, Chiba 274-8501, Japan, Email: itou.kennichinihon-u.ac.jp

K.-i. Itoh, M. Hayakawa, R. Abe, S. Takahashi, K. Hasegawa, T. Aoyama, Synthesis, 2021, 53, 4636-4643.

DOI: 10.1055/a-1581-0235

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Abstract

Silica gel-supported sodium hydrogen sulfate (NaHSO₄/SiO₂) or Amberlyst 15 catalyze the formation of nitrile oxides from α-nitro ketones. A subsequent in situ 1,3-dipolar cycloaddition to alkynes provides 3-acylisoxaszoles in very good yields. The heterogeneous catalysts can easily be recovered and reused.

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Key Words

isoxazoles, nitrile oxides, 1,3-dipolar cycloaddition, solid acid, supported reagents, acidic polymer, facile synthesis

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ID: J66-Y2021