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An efficient solvent-free synthesis of isoxazolyl-1,4-dihydropyridines on solid support SiO2 under microwave irradiation

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Abstract

An efficient synthesis of 1,4-dihydropyridines was developed. 1,4-Dihydropyridines were synthesized starting from various 3-substituted isoxazolyl-5-carbaldehydes, ethyl acetoacetate, and ammonium acetate under microwave irradiation and solvent-free conditions (86–96 %), and were characterized by HRMS, FT-IR, 1H NMR, and 13C NMR spectroscopy. Solid support SiO2 was found to possess favorable catalysis and dispersancy for the condensation reaction. The merits of the method included the environmental friendly reaction conditions, simple operation, extensive substrates, good yields and reuse of the SiO2. Moreover, the crystal structure of compound diethyl 4-[3-(2-methoxyphenyl)isoxazol-5-yl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate in orthorhombic Pbca space group was presented.

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Acknowledgments

We are grateful to Mr Ch. Y. Wang for NMR spectra, Mr Zh. L. Wei for mass spectra, and Ms L. Ye and Ms Q. Su for X-ray.

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Authors and Affiliations

  1. College of Chemistry, Jilin University, Changchun, 130012, People’s Republic of China

    Dawei Zhang, Xiaodong Chen, Xue Guo, Yumin Zhang, Yaya Hou, Tianqi Zhao & Qiang Gu

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  1. Dawei Zhang
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  2. Xiaodong Chen
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  3. Xue Guo
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  4. Yumin Zhang
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Correspondence to Qiang Gu.

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Zhang, D., Chen, X., Guo, X. et al. An efficient solvent-free synthesis of isoxazolyl-1,4-dihydropyridines on solid support SiO2 under microwave irradiation. Monatsh Chem 147, 1605–1614 (2016). https://doi.org/10.1007/s00706-016-1657-2

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