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Efficient synthesis of bis-isoxazole ethers via 1,3-dipolar cycloaddition catalysed by Zn/Zn2+ and their antifungal activities

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Abstract

An efficient method was developed for synthesising isoxazoles. A series of novel bis-isoxazole ether compounds VI, VII and VIII were synthesised starting from different substituted aldehydes (I) via a 1,3-dispolar cycloaddition using Zn/Zn2+ as a catalyst; these were characterised by FT-IR, HRMS, 1H NMR and 13C NMR spectroscopy. In addition, the antimicrobial properties of the synthesised products were investigated. The synthesised compounds exhibited significant antifungal activities in comparison with the standard drugs, fluconazole and itraconazole. It was found that Candida albicans was sensitive to 2-substituted phenyl bis-isoxazole ethers bearing pyridyl.

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Authors and Affiliations

  1. College of Chemistry, Jilin University, Changchun, 130012, China

    Da-Wei Zhang, Hong-Wei Liu, Tian-Qi Zhao, Yu-Min Zhang & Qiang Gu

  2. College of Life Science, Jilin University, Changchun, 130012, China

    Feng Lin & Bo-Chao Li

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  1. Da-Wei Zhang
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  2. Feng Lin
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  3. Bo-Chao Li
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  4. Hong-Wei Liu
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  5. Tian-Qi Zhao
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  6. Yu-Min Zhang
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  7. Qiang Gu
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Correspondence to Qiang Gu.

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Zhang, DW., Lin, F., Li, BC. et al. Efficient synthesis of bis-isoxazole ethers via 1,3-dipolar cycloaddition catalysed by Zn/Zn2+ and their antifungal activities. Chem. Pap. 69, 1500–1511 (2015). https://doi.org/10.1515/chempap-2015-0161

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