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A simple method for the rapid synthesis of 2-amino-7,7-dimethyl-5-oxo-1,4-diaryl-hexahydroquinoline-3-carboxamide derivatives

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Abstract

Simple synthesis of oxoquinoline carboxamide derivatives via one-pot, multi-component reaction of enaminones derived from the addition of dimedone to various anilines with aromatic aldehydes and cyanoacetamide is described. Optimal reaction conditions for the synthesis of products were obtained, when EtOH/H2O (1:1) was used as the solvent at 80 °C, in the presence of piperidine as the catalyst. The reactions are completed within 5–25 min, in good to high yields (74–85%). This protocol involves Michael reaction, imine-enamine tautomerization, and cyclization sequences. The structures of products were deduced from their IR, mass, 1H NMR, and 13C NMR spectra. This method includes some important aspects including simple operation under mild conditions, easy accessibility of reactants, workup procedure, high atom economy, and the use of ethanol/water as a green media.

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Acknowledgements

Financial support of this research from Imam Khomeini International University, Iran, is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Imam Khomeini International University, Qazvin, Iran

    Fahimeh Sadat Hosseini & Mohammad Bayat

Authors
  1. Fahimeh Sadat Hosseini
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  2. Mohammad Bayat
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Correspondence to Mohammad Bayat.

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The authors declare no competing financial interest.

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Supporting Information Available.

Full experimental details and copies of 1H, 13C NMR, IR, and mass spectra of products are provided. (DOC 18,939 kb)

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Hosseini, F.S., Bayat, M. A simple method for the rapid synthesis of 2-amino-7,7-dimethyl-5-oxo-1,4-diaryl-hexahydroquinoline-3-carboxamide derivatives. J IRAN CHEM SOC 17, 2267–2274 (2020). https://doi.org/10.1007/s13738-020-01920-3

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  • DOI: https://doi.org/10.1007/s13738-020-01920-3

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