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Synthesis of 5-alkoxy-4-amino-3-bromo-2(5H)-furanones containing benzene rings

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Abstract

Using KF as base and THF as solvent, different 5-alkoxy-3,4-dibromo-2(5H)-furanones were reacted with amines containing a benzene ring structure by Michael addition–elimination reaction at room temperature or 40 °C to give twenty-three 5-alkoxy-4-amino-3-bromo-2(5H)-furanones containing benzene rings, with yields of 21–86 % (mostly over 64 %). The structures of all the newly synthesized compounds were elucidated and confirmed by FTIR, UV, 1H NMR, 13C NMR, and mass spectroscopy, elemental analysis, and X-ray single-crystal diffraction. This rapid synthesis of the series of 2(5H)-furanones derivatives with different bioactive units is not only an important synthetic strategy for 2(5H)-furanone derivatives but also a basis for synthesis of potential drug molecules for activity testing.

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Acknowledgments

The authors’ are grateful to the National Natural Science Foundation of China (no. 20772035), the Third Talents Special Funds of Guangdong Higher Education (no. Guangdong-Finance-Education [2011]431) and the Natural Science Foundation of Guangdong Province (no. S2011010001556) for financial support.

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Authors and Affiliations

  1. School of Chemistry and Environment, South China Normal University, Guangzhou, 510006, People’s Republic of China

    Fu-Ling Xue, Jian-Xiao Li, Zhao-Yang Wang, Jin-Feng Xiong & Di Li

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  1. Fu-Ling Xue
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  2. Jian-Xiao Li
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Correspondence to Zhao-Yang Wang.

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Xue, FL., Li, JX., Wang, ZY. et al. Synthesis of 5-alkoxy-4-amino-3-bromo-2(5H)-furanones containing benzene rings. Res Chem Intermed 39, 1153–1168 (2013). https://doi.org/10.1007/s11164-012-0674-y

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