Synthesis of bicyclic isoxazoles and isoxazolines via intramolecular nitrile oxide cycloaddition

Wen Chang Chen, Veerababurao Kavala, Yu Hsuan Shih, Yu Hsuan Wang, Chun Wei Kuo, Tang Hao Yang, Chia Yu Huang, Hao Hsiang Chiu, Ching Fa Yao

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Abstract

An efficient and straight forward procedure for the syntheses of bicyclic isoxazole/isoxazoline derivatives from the corresponding dimethyl-2-(2-nitro-1-aryl/alkyl)-2-(prop-2-yn-1yl)malonates or dimethyl 2-allyl-2-(2-nitro-1-aryl/alkyl ethyl)malonate is described. High yields and simple operations are important features of this methodology. bicyclic isoxazole/isoxazolines; cycloaddition; nitrile oxide; nitroalkane; Yamaguchi reagent.

Original languageEnglish
Pages (from-to)10910-10927
Number of pages18
JournalMolecules
Volume20
Issue number6
DOIs
Publication statusPublished - 2015 Jun 1

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Chen, W. C., Kavala, V., Shih, Y. H., Wang, Y. H., Kuo, C. W., Yang, T. H., Huang, C. Y., Chiu, H. H., & Yao, C. F. (2015). Synthesis of bicyclic isoxazoles and isoxazolines via intramolecular nitrile oxide cycloaddition. Molecules, 20(6), 10910-10927. https://doi.org/10.3390/molecules200610910