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Three-component domino [3+2] heterocyclization leading to pyran-3-yl-substituted fused pyrroles

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Abstract

Concise and efficient three-component domino [3+2] heterocyclization to pyran-3-yl-substituted fused pyrroles promoted by HOAc have been developed under microwave irradiation. The reactions showed broad scopes of substrates which can employ a wide range of readily available arylglyoxal monohydrate and N-aryl enaminones. The structures of products 4 have been unambiguously determined by NMR and HRMS analyses. The single crystal of 4a was further confirmed by X-ray diffraction analysis.

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Scheme 1
Fig. 1
Scheme 2

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Notes

  1. Crystal data for 4a: C29H27NO4, crystal dimension 0.37 × 0.18 × 0.14 mm, monoclinic, space group P2(1)/n, a = 11.2339(15) Å, b = 10.6994(12) Å, c = 20.666(2) Å, α = 90.00°, β = 100.6440(10)°, γ = 90.00°, V = 2,441.2(5) Å3, Mr = 453.52, Z = 4, Dc = 1.234 Mg/m3, λ = 0.71073 Å, μ(Mo Kα) = 0.082 mm−1, F(000) = 960, R = 0.0715, S = 1.032.

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Acknowledgments

We are grateful for financial support from the NSFC (Nos. 21272095 and 21102124), Jiangsu Science and Technology Support Program (No. BE2011045), the Qing Lan Project (12QLG006), and National Students’ Innovative Training Program (No. 201210320017).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, P. R. China

    Shuang-Shuang Wang, Qi-Wei Zhu, Shuai Liu, Yang Yang, Zhi-Tong Wang, Bo Jiang & Shu-Jiang Tu

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  1. Shuang-Shuang Wang
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  2. Qi-Wei Zhu
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  4. Yang Yang
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  5. Zhi-Tong Wang
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  6. Bo Jiang
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  7. Shu-Jiang Tu
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Correspondence to Bo Jiang or Shu-Jiang Tu.

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Shuang-Shuang Wang, Qi-Wei Zhu, Shuai Liu, Yang Yang, and Zhi-Tong Wang made equal contributions to this work.

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Wang, SS., Zhu, QW., Liu, S. et al. Three-component domino [3+2] heterocyclization leading to pyran-3-yl-substituted fused pyrroles. Res Chem Intermed 41, 2879–2889 (2015). https://doi.org/10.1007/s11164-013-1396-5

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