Synthesis of 5-alkoxy-4-amino-3-bromo-2(5H)-furanones containing benzene rings |
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Authors: | Fu-Ling Xue Jian-Xiao Li Zhao-Yang Wang Jin-Feng Xiong Di Li |
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Institution: | 1. School of Chemistry and Environment, South China Normal University, Guangzhou, 510006, People’s Republic of China
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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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