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Copper-catalyzed C2-selective alkynylation of chromones via 1,4-conjugate addition

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Abstract

Copper-catalyzed selective alkynylation with N-propargyl carboxamides as nucleophiles has been successfully developed for the synthesis of C2-functionalized chromanones. Under optimized reaction conditions, 21 examples were obtained in one-pot procedure through 1,4-conjugate addition. This protocol features readily available feedstocks, easy operations, and moderate to good yields, which provides viable access to pharmacologically active C2-functionalized chromanones.

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Acknowledgements

The authors would like to thank the National Natural Science Foundation of China (51973042), Major Project of Natural Science Foundation of Guizhou Province [Grant No. QKHJC-ZK(2021) ZD048], the Science and Technology Research Program of Chongqing Municipal Education Commission (KJQN201801321 and KJQN202101340), the Natural Science Foundation Project of CQ CSTSC (cstc2018jszx-cyzdX0023 and cstc2021jcyj-bsh0233), and Chongqing University of Arts and Sciences: Program for Talents Introduction (R2021FYX05 and P2022YX10). We would also like to thank Ms HZ. Liu for obtaining the LC/MS, HRMS, and NMR data.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Guizhou University, Guiyang, 550025, China

    Yan-Wu Li & Meng-Lan Lv

  2. College of Pharmacy, National & Local Joint Engineering Research Center of Targeted and Innovative Therapeutics, IATTI, Chongqing University of Arts and Sciences, Chongqing, 402160, China

    Yan-Wu Li, Jie Lei & Zhong-Zhu Chen

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Yan-Wu Li carried out the experiments. Jie Lei wrote the manuscript with support from Zhong-Zhu Chen. Meng-Lan Lv supervised the project.

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Correspondence to Jie Lei, Zhong-Zhu Chen or Meng-Lan Lv.

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Li, YW., Lei, J., Chen, ZZ. et al. Copper-catalyzed C2-selective alkynylation of chromones via 1,4-conjugate addition. Mol Divers 28, 125–131 (2024). https://doi.org/10.1007/s11030-023-10625-7

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