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Formation of furo[3,2-c]quinolone-2-carbonitriles and 4-oxo-4,5-dihydrofuro[3,2-c]quinolone-2-carboxamides from reaction of quinoline-2,4-diones with 2-[bis(methylthio)methylene]malononitrile

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Abstract

Quinoline-2,4-diones reacted with 2-[bis(methylthio)methylene]malononitrile in DMF/Et3N to produce 3-(methylthio)-4-oxo-4,5-dihydrofuro[3,2-c]quinolone-2-carbonitriles and 3-(methylthio)-4-oxo-4,5-dihydrofuro[3,2-c]quinolone-2-carboxamides in state of 2-imino-substituted 4-(methylthio)-5,6-dihydro-2H-pyrano[3,2-c]quinolone-3-carbonitriles. The structures of all new products were proved using NMR, IR, and mass spectral data. The possible mechanism for the reaction is also discussed.

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Acknowledgements

The authors also thank DFG Foundation for providing Prof Ashraf A. Aly, 1-month fellowship enabling him to carry out the compounds analysis in Karlsruhe Institute of Technology, Karlsruhe, Germany in July–August 2019.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Minia University, 61519, El-Minia, Egypt

    Ashraf A. Aly & Asmaa H. Mohamed

  2. Department of Chemistry, Faculty of Science, Al-Azhar University, Assiut, Egypt

    Esam A. Ishak

  3. Department of Chemistry, College of Science and Arts, Jouf University, Alquurrayate, KSA, Saudi Arabia

    Esam A. Ishak

  4. Science and Technology Unit (STU), Umm Al Qura University, Makkah, KSA, Saudi Arabia

    Ahmed M. Shwaky

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  1. Ashraf A. Aly
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  2. Esam A. Ishak
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  4. Asmaa H. Mohamed
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Correspondence to Ashraf A. Aly.

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Aly, A.A., Ishak, E.A., Shwaky, A.M. et al. Formation of furo[3,2-c]quinolone-2-carbonitriles and 4-oxo-4,5-dihydrofuro[3,2-c]quinolone-2-carboxamides from reaction of quinoline-2,4-diones with 2-[bis(methylthio)methylene]malononitrile. Monatsh Chem 151, 223–229 (2020). https://doi.org/10.1007/s00706-019-02541-0

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  • DOI: https://doi.org/10.1007/s00706-019-02541-0

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