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A highly regioselective synthesis of functionalized furo[3,2-a]acridine derivatives via a three-component reaction

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Abstract

A three-component reaction of benzaldehyde, methyl 5-aminobenzofuran-2-carboxylate, and cyclohexane-1,3-dione in refluxing EtOH under catalyst-free conditions regioselectively gave furo[3,2-a]acridine rather than furo[3,2-b]acridine derivatives. This new procedure has the advantages of one-pot reaction, catalyst-free nature, high yield, and high regioselectivity.

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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 Synthesis for Functional Materials, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, People’s Republic of China

    Yan Zhang, Jing Xu, Mei-Mei Zhang & Xiang-Shan Wang

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  1. Yan Zhang
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  2. Jing Xu
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  3. Mei-Mei Zhang
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  4. Xiang-Shan Wang
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Correspondence to Xiang-Shan Wang.

Electronic supplementary material

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11164_2015_1998_MOESM1_ESM.pdf

Copies of NMR spectra for compounds 4a–m are available free of charge via the Internet. Crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-1051303. Copies of available material can be obtained, free of charge, on application to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk]. (PDF 472 kb)

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Zhang, Y., Xu, J., Zhang, MM. et al. A highly regioselective synthesis of functionalized furo[3,2-a]acridine derivatives via a three-component reaction. Res Chem Intermed 41, 9917–9927 (2015). https://doi.org/10.1007/s11164-015-1998-1

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  • DOI: https://doi.org/10.1007/s11164-015-1998-1

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