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Oleylamine-catalyzed Tandem Knoevenagel/Michael Addition of 1,3-Cyclohexanediones with Aromatic Aldehydes

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Abstract

A convenient and efficient method was developed for the synthesis of 2,2′-(arylmethylene)bis(3-hydrox- ycyclohex-2-enone) derivatives via the oleylamine-catalyzed tandem Knoevenagel/Michael addition reactions of aromatic aldehydes and cyclohexane-1,3-diones. This transformation proceeded without any metal catalyst in non-toxic solvent at room temperature with high isolated yields. A plausible mechanism for this process was pro-posed.

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Authors and Affiliations

  1. Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-based Materials(State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu, 241000, P. R. China

    Xinwei He, Yuhao Wu, Chenli Fan, Peng Lu, Youpeng Zuo & Yongjia Shang

  2. Department of Material Engineering, Wuhu Institute of Technology, Wuhu, 241003, P. R. China

    Chenli Fan

Authors
  1. Xinwei He
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  2. Yuhao Wu
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  3. Chenli Fan
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  4. Peng Lu
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  5. Youpeng Zuo
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  6. Yongjia Shang
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Corresponding authors

Correspondence to Xinwei He or Yongjia Shang.

Additional information

Supported by the National Natural Science Foundation of China(Nos.21772001, 21372008), the Natural Science Foundation of Education Administration of Anhui Province, China(No.KJ2016A267), the Special and Excellent Research Fund of Anhui Normal Universit and the Doctoral Scientific Research Foundation of Anhui Normal University, China(No.2016XJJ110).

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He, X., Wu, Y., Fan, C. et al. Oleylamine-catalyzed Tandem Knoevenagel/Michael Addition of 1,3-Cyclohexanediones with Aromatic Aldehydes. Chem. Res. Chin. Univ. 34, 186–190 (2018). https://doi.org/10.1007/s40242-018-7320-1

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  • DOI: https://doi.org/10.1007/s40242-018-7320-1

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