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Green synthesis of polysubstituted quinoline and benzoquinoline derivatives in ionic liquid via a three-component reaction

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Abstract

A three-component reaction of aldehyde, (E)-3-aminobut-2-enenitrile and dimedone in ionic liquids, gave 1,4,5,6,7,8-hexahydro-2,7,7-trimethyl-5-oxo-4-arylquinoline-3-carbonitrile derivatives at 50 °C. Using 2-hydroxynaphthalene-1,4-dione to replace dimedone at the same reaction conditions resulted in another series of polysubstituted benzo[h]quinoline derivatives in high yields. This method involves the advantages of mild conditions, high yields, one-pot synthesis, and an environmentally benign procedure.

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Acknowledgments

We are grateful to the National Natural Science Foundation of China (No.51174201), the Open Foundation of Southwest University of Science and Technology (No.11zxjk10), a Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions, and College Industrialization Project (JHB2012-31) of Jiangsu Province for financial support.

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Authors and Affiliations

  1. School of Chemical Engineering and Technology, China University of Mining and Technology, Xuzhou, 221116, Jiangsu, People’s Republic of China

    Yong Sun & Pei-Jun Cai

  2. 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

    Xiang-Shan Wang

Authors
  1. Yong Sun
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  2. Pei-Jun Cai
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  3. Xiang-Shan Wang
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Correspondence to Pei-Jun Cai or Xiang-Shan Wang.

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Sun, Y., Cai, PJ. & Wang, XS. Green synthesis of polysubstituted quinoline and benzoquinoline derivatives in ionic liquid via a three-component reaction. Res Chem Intermed 41, 7393–7403 (2015). https://doi.org/10.1007/s11164-014-1819-y

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  • DOI: https://doi.org/10.1007/s11164-014-1819-y

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