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Synthesis of phenylacetylene containing 1,2,3-triazole group

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Abstract

Bromination of (E)-1-[4-(2-carboxy-vinyl)phenyl]-[1,2,3]triazole-4-carboxylic acid ethyl ester, which was synthesized in 90% yield by a Huisgen-type [3 + 2]-cycloaddition reaction between 3-(4-azidophenyl) acrylic acid and ethyl propiolate, in CHCl3 followed by a debrominative decarboxylation reaction with Et3N in DMF under microwave irradiation condition afforded stereoselective (Z)-1-(4-(2-bromovinyl)phenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester in 94% yield. Treatment of (Z)-1-(4-(2-bromovinyl)phenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester with EtONa in DMF afforded 1-(4-ethynylphenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester in a yield of 90%.

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Acknowledgments

This work was supported by Naturale Science Foundation of China (No. 30873153), the Key Projects of Shanghai in Biomedical (No. 08431902700) and the Scientific Research Foundation of State Education Ministry for the Returned Overseas Chinese Scholars. We would like to thank the Center for Instrumental Analysis, Tongji University, China.

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Authors and Affiliations

  1. Department of Chemistry, Tongji University, Siping Road 1239, Shanghai, 200092, China

    Wensheng Zhang, Changhui Su, Yubo Jiang & Chunxiang Kuang

  2. Department of Chemistry, Jiaozuo Teachers’ College, Jiaozuo, 454001, China

    Wensheng Zhang

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  1. Wensheng Zhang
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Correspondence to Chunxiang Kuang.

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Zhang, W., Su, C., Jiang, Y. et al. Synthesis of phenylacetylene containing 1,2,3-triazole group. Res Chem Intermed 35, 589–595 (2009). https://doi.org/10.1007/s11164-009-0065-1

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