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Facile synthesis of new pyrano[3,2-c]quinolones via the reaction of quinolin-2-ones with ethene-1,2,3,4-tetracarbonitrile

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Abstract

Synthesis of heteroannulated pyrano[3,2-c]quinolones was established starting from the reaction of 4-hydroxyquinolin-2-ones with ethene-1,2,3,4-tetracarbonitrile. Several conditions were carried out, and the corresponding product yields were illustrated. The neutral and non-polar condition was the best procedure for product formation. The structure of products was elucidated by NMR, IR, mass spectra, and elemental analysis. X-ray structure analysis was also used to elucidate the structure of the obtained products. The mechanism of products formation was also discussed.

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Acknowledgements

The authors thank DFG for providing Ashraf A. Aly with a fellowship, enabling him to conduct the compound analysis at the Karlsruhe Institute of Technology, Karlsruhe, Germany.

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Authors and Affiliations

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

    Ashraf A. Aly, Hisham A. Abd El-Naby, Essam Kh. Ahmed, Raafat M. Shaker, Sageda A. Gedamy & Lamiaa E. Abd El-Haleem

  2. Department of Chemistry, University of Helsinki, A. I. Virtasen aukio I, P.O. Box 55, 00014, Helsinki, Finland

    Martin Nieger

  3. Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany

    Stefan Bräse

  4. Institute of Biological and Chemical Systems – Functional Molecular Systems (IBCS-FMS), Karlsruhe Institute of Technology, Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany

    Stefan Bräse

Authors
  1. Ashraf A. Aly
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  2. Hisham A. Abd El-Naby
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  3. Essam Kh. Ahmed
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  4. Raafat M. Shaker
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  5. Sageda A. Gedamy
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  6. Martin Nieger
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  7. Stefan Bräse
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  8. Lamiaa E. Abd El-Haleem
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Corresponding author

Correspondence to Ashraf A. Aly.

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Dedicated for the memory of Professor Dr. Raafat Mohamed Shaker.

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Aly, A.A., El-Naby, H.A.A., Ahmed, E.K. et al. Facile synthesis of new pyrano[3,2-c]quinolones via the reaction of quinolin-2-ones with ethene-1,2,3,4-tetracarbonitrile. Monatsh Chem 153, 277–284 (2022). https://doi.org/10.1007/s00706-022-02903-1

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  • DOI: https://doi.org/10.1007/s00706-022-02903-1

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