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Synthesis of N-[5-alkoxy-2(5H)-furanonyl] amino acid propargyl esters

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Abstract

Using K2CO3 as a base and CH3CN as solvent, different kinds of N-[5-alkoxy-2(5H)-furanonyl] amino acids were reacted with propargyl bromide via substitution reaction at 40 °C to give 16 N-[5-alkoxy-2(5H)-furanonyl] amino acid propargyl esters with the yields of 44–85% (mostly over 74%). The structures of all newly synthesized compounds were elucidated and confirmed by FTIR, UV, 1H NMR, 13C NMR, MS, and elemental analysis. The rapid, efficient, and brief synthesis of the series propargyl esters with multiple bioactive units, will afford not only a basis for the activity test of potential drug molecules, but also an important synthetic strategy for 2(5H)-furanone derivatives with polyfunctional groups.

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Acknowledgments

We are grateful to the National Natural Science Foundation of China (No. 20772035) and the Natural Science Foundation of Guangdong Province (No. 5300082) 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

    Yue-He Tan, Zhao-Yang Wang, Ji Qi, Jin-Feng Xiong & Mei-Xiang Lv

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  1. Yue-He Tan
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  2. Zhao-Yang Wang
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  3. Ji Qi
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Correspondence to Zhao-Yang Wang.

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Tan, YH., Wang, ZY., Qi, J. et al. Synthesis of N-[5-alkoxy-2(5H)-furanonyl] amino acid propargyl esters. Res Chem Intermed 38, 925–936 (2012). https://doi.org/10.1007/s11164-011-0429-1

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