ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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

Da-Wei Zhang, Feng Lin, Bo-Chao Li, Hong-Wei Liu, Tian-Qi Zhao, Yu-Min Zhang, and Qiang Gu

College of Chemistry, Jilin University, Changchun 130012, China

E-mail: guq@jlu.edu.cn

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.

Keywords: bis-isoxazole ether – 1,3-dispolar cycloaddition – Zn/Zn2+ – anti-fungal activity – nitrile oxide

Full paper is available at www.springerlink.com.

DOI: 10.1515/chempap-2015-0161

Chemical Papers 69 (11) 1500–1511 (2015)