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Copper-catalyzed Ullmann reaction for the synthesis of fused hexacyclic heterocycles containing naphthyridine, acridine, and pyrazole (imidazole) moieties

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Abstract

Consecutive Knoevenagel condensation, Michael addition, cyclization, and Ullmann Csp2-N coupling reactions took place in the Domino reaction of o-halogenated benzaldehydes, tert-butyl 2,4-dioxopiperidine-1-carboxylate, and 1H-indazol-6-amine or 3H-benzo[d]imidazol-5-amine catalyzed by CuI. It gave series of fused hexacyclic heterocycles containing naphthyridine, acridine, and pyrazole (imidazole) moieties in one-pot under ligand-free conditions.

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Acknowledgments

We are grateful to the Major Natural Science Foundation of Jiangsu Province (14KJA150004) and a project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions for financial support.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials,, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, People’s Republic of China

    Yong-Gang Ma, Wen-Wen Qiang, Chao Li, Mei-Mei Zhang & Xiang-Shan Wang

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  1. Yong-Gang Ma
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  2. Wen-Wen Qiang
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  3. Chao Li
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  4. Mei-Mei Zhang
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  5. Xiang-Shan Wang
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Corresponding author

Correspondence to Xiang-Shan Wang.

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Ma, YG., Qiang, WW., Li, C. et al. Copper-catalyzed Ullmann reaction for the synthesis of fused hexacyclic heterocycles containing naphthyridine, acridine, and pyrazole (imidazole) moieties. Monatsh Chem 147, 1233–1242 (2016). https://doi.org/10.1007/s00706-015-1625-2

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  • DOI: https://doi.org/10.1007/s00706-015-1625-2

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