Open Access
CC BY-NC-ND 4.0 · Synthesis 2021; 53(24): 4636-4643
DOI: 10.1055/a-1581-0235
paper

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

Autoren

  • Ken-ichi Itoh

    a   Department of Liberal Arts and Science, College of Science and Technology, Nihon University, 7-24-1, Narashinodai, Funabashi-shi, Chiba 274-8501, Japan
  • Mamiko Hayakawa

    b   Department of Material and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan
  • Rina Abe

    b   Department of Material and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan
  • Shinji Takahashi

    b   Department of Material and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan
  • Kenta Hasegawa

    b   Department of Material and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan
  • Tadashi Aoyama

    b   Department of Material and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan

This work was supported by JSPS KAKENHI [Grant-in-Aid for Scientific Research (C) 19K05570].


Graphical Abstract

Abstract

Nitrile oxides were formed from α-nitro ketones using silica gel-supported sodium hydrogen sulfate (NaHSO4/SiO2) or Amberlyst 15 as solid acid catalyst, and then the corresponding 3-acylisoxaszoles were obtained by reacting with alkynes via the 1,3-dipolar [3+2] cyclo­addition. These heterogeneous catalysts are easily separable from the reaction mixture and reused. This synthetic method provides a facile, efficient, and reusable production of 3-acylisoxazoles.

Supporting Information

Primary Data



Publikationsverlauf

Eingereicht: 31. Mai 2021

Angenommen nach Revision: 29. Juli 2021

Accepted Manuscript online:
09. August 2021

Artikel online veröffentlicht:
08. September 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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