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Facile synthesis of indole- or benzofuran-fused benzo[a]carbazole-1,4-diones using a tandem two-step reaction sequence

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Abstract

An efficient three-step approach was developed to assemble indole- or benzofuran-fused benzocarbazole-1,4-diones in 42–53% overall yield. This approach includes AgOAc-promoted oxidative cyclization of 2,6-di-bromocyclohexene-1,4-dione with indol-3-ylpropanoid acid, condensation of the resulting bromocarbazole intermediates with phenols or anilines, followed by Pd(OAc)-catalyzed cyclization. Such convenient synthetic protocol and the novelty of the corresponding products will largely assist our drug design and development program.

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Authors and Affiliations

  1. Department of Chemistry, Capital Normal University, 100048, Beijing, China

    Shanghui Tu & Wenxiang Hu

  2. Synthetic Organic and Medicinal Chemistry Laboratory (SOMCL), Shanghai Institute of Materia Medica (SIMM), 201203, Shanghai, China

    Shanghui Tu, Chunyong Ding, Fulong Li & Ao Zhang

  3. Department of Medicinal Chemistry, China Pharmaceutical University, 21009, Nanjing, China

    Chunyong Ding, Fulong Li & Qizheng Yao

Authors
  1. Shanghui Tu
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  2. Chunyong Ding
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  3. Wenxiang Hu
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  4. Fulong Li
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  5. Qizheng Yao
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  6. Ao Zhang
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Correspondence to Ao Zhang.

Additional information

Part of this study has been presented in the 2nd International Symposium on Combinatorial Sciences in Biology, Chemistry, Catalysts and Materials in Beijing on September 19–23, 2009.

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Tu, S., Ding, C., Hu, W. et al. Facile synthesis of indole- or benzofuran-fused benzo[a]carbazole-1,4-diones using a tandem two-step reaction sequence. Mol Divers 15, 91–99 (2011). https://doi.org/10.1007/s11030-010-9241-x

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