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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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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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Keywords

  • Quinolin-2,4-diones
  • 2-[Bis(methylthio)methylene]malononitrile
  • Furo[3,2-c]quinolone-3-carbonitriles
  • Mechanism