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Synthesis of highly functionalized 3,4-cyclohexane-annelated coumarins

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Abstract

Efficient synthetic access to highly functionalized 3,4-cyclohexane-annelated coumarins has been achieved by combining two methods. First, the important intermediates multisubstituted cyclic β-keto esters were prepared conveniently by condensing a variety of benzaldehydes with ethyl acetoacetate. A series of highly functionalized 3,4-cyclohexane-annelated coumarins were then synthesized by Amberlyst-15-catalyzed Pechmann condensation of multisubstituted cyclic β-keto esters with phenols. This synthetic method has the advantages of mild reaction conditions, good tolerance of a variety of functional groups, and satisfactory yields.

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Acknowledgments

The authors gratefully acknowledge financial support from the Provincial Key Project of Natural Science Research for Colleges and Universities of Anhui Province of China (KJ2011A091).

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Authors and Affiliations

  1. School of Chemical Engineering, Anhui University of Science and Technology, No.168, Shungeng Middle Road, Huainan, 232001, Anhui, People’s Republic of China

    Chao-Yue Chen, Xiao-Mei Zhang, Jian-Jun Shi & Jie He

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  1. Chao-Yue Chen
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  2. Xiao-Mei Zhang
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  3. Jian-Jun Shi
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  4. Jie He
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Correspondence to Chao-Yue Chen.

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Chen, CY., Zhang, XM., Shi, JJ. et al. Synthesis of highly functionalized 3,4-cyclohexane-annelated coumarins. Res Chem Intermed 41, 583–593 (2015). https://doi.org/10.1007/s11164-013-1212-2

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  • DOI: https://doi.org/10.1007/s11164-013-1212-2

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