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Heterogeneous Synthesis of Indole-2-Carboxylic Esters Via Bischler Cyclization Under the Catalysis of Sulfonic Acid-Functionalized SBA-15 Silicas

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Abstract

Phenylsulfonic acid-functionalized SBA-15 silica was found to be an efficient heterogeneous acid catalyst in Bischler cyclization for the synthesis of indole-2-carboxylic esters. Under the optimized conditions, a wide range of substituted 4-nitrobenzyl 3-hydroxy-2-(N-methyl-N-arylamino)-2-enoates could be smoothly transformed to the corresponding 4-nitrobenzyl indole-2-carboxylates in excellent yields (87–99 %). Moreover, the catalyst could be conveniently recovered and reused at least four times without significant loss of catalytic activity.

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Acknowledgments

This work was supported by the National Natural Science Foundations of China (21376224). We also thank the support from “Zhejiang Key Course of Chemical Engineering and Technology” and “Zhejiang Key Laboratory of Green Pesticides and Cleaner Production Technology of Zhejiang Province” of Zhejiang University of Technology.

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Authors and Affiliations

  1. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310032, China

    Nan Sun, Xiayue Zhu, Jiali Luo, Weimin Mo, Baoxiang Hu & Xinquan Hu

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  1. Nan Sun
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  2. Xiayue Zhu
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  3. Jiali Luo
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  4. Weimin Mo
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  5. Baoxiang Hu
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  6. Xinquan Hu
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Corresponding authors

Correspondence to Nan Sun or Xinquan Hu.

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Sun, N., Zhu, X., Luo, J. et al. Heterogeneous Synthesis of Indole-2-Carboxylic Esters Via Bischler Cyclization Under the Catalysis of Sulfonic Acid-Functionalized SBA-15 Silicas. Catal Lett 145, 1643–1649 (2015). https://doi.org/10.1007/s10562-015-1564-x

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  • DOI: https://doi.org/10.1007/s10562-015-1564-x

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