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Tröger’s base derivative-catalyzed one-step one-pot synthesis of chromenofuroindoles and naphthofuroindoles

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Abstract

A series of N2,N8-bis(nitrogen-containing heterocycle)-yl-2,8-dicarboxamide-Tröger’s bases were synthesized. The most efficient one, N2,N8-di(4H-1,2,4-triazol-4-yl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-dicarboxamide (4d), was used as bifunctional catalyst to promote the one-step one-pot preparation of the chromeno[3′,4′:4,5]furo[2,3-b]indoles or naphtho[2′,3′:4,5]furo[2,3-b]indoles with CuI via the cascade Aldol-[4 + 1]cycloaddition-intramolecular Ullmann reaction of 4-hydroxycoumarin (or 2-hydroxy-1,4-naphoquinone), substituted benzaldehydes and isocyanide. A reasonable catalysis mechanism was investigated by the 1H NMR titration and control experiments.

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Acknowledgements

We are grateful to the foundation of the “Priority Academic Program Development of Jiangsu Higher Education Institutions” for financial support.

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Author notes

  1. Hang Zhou and Ya-wen Sun contributed equally to this work.

Authors and Affiliations

  1. School of Chemistry and Material Science, Jiangsu Normal University, Xuzhou, Jiangsu, 221116, People’s Republic of China

    Hang Zhou, Ya-wen Sun, Jiang-biao Xu & Pei-yao Liang

  2. Jiangsu Province Engineering Research Center of Cardiovascular Drugs Targeting Endothelial Cell, School of Life Science, Jiangsu Normal University, Xuzhou, Jiangsu, 221116, People’s Republic of China

    Yu Wan, Rui Yuan & Hui Wu

Authors
  1. Hang Zhou
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  2. Ya-wen Sun
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  3. Jiang-biao Xu
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Correspondence to Hui Wu.

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Zhou, H., Sun, Yw., Xu, Jb. et al. Tröger’s base derivative-catalyzed one-step one-pot synthesis of chromenofuroindoles and naphthofuroindoles. Res Chem Intermed 48, 1763–1772 (2022). https://doi.org/10.1007/s11164-022-04664-2

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