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Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 3, pp 635–644 | Cite as

Synthesis of spiro[indoline-3,4′-pyrano[3,2-c]quinolone]-3′-carbonitriles

  • Ashraf A. Aly
  • Essmat M. El-Sheref
  • Aboul-Fetouh E. Mourad
  • Alan B. Brown
  • Stefan Bräse
  • Momtaz E. M. Bakheet
  • Martin Nieger
Original Paper

Abstract

Quinoline-2,4-diones reacted with 2-(2-oxo-1,2-dihydroindol-3-ylidene)malononitrile in pyridine to give 2′-amino-2,5′-dioxo-5′,6′-dihydrospiro(indoline-3,4′-pyrano[3,2-c]quinoline)-3′-carbonitriles in good to excellent yields. The structures of all new products were proven using one- and two-dimensional NMR, IR, and mass spectral data, and in five cases X-ray structural analyses. The possible mechanism for the reaction is also discussed.

Graphical abstract

Keywords

Quinolin-2,4-diones Isatinemalononitrile Spiro-compounds X-ray analysis 

Notes

Acknowledgements

The NMR spectrometer at Florida Institute of Technology was purchased with the assistance of the U.S National Science Foundation (CHE 03 42251). Prof AA Aly is thankful to DFG foundation for the financial support of his fellowship accommodation in the Karlsruhe Institut für Technologie (KIT), Institute of Organic Chemistry, Karlsruhe, Germany.

Supplementary material

706_2017_2078_MOESM1_ESM.xls (45 kb)
Supplementary material 1 (XLS 45 kb)
706_2017_2078_MOESM2_ESM.rar (9.3 mb)
Supplementary material 2 (RAR 9495 kb)

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Copyright information

© Springer-Verlag GmbH Austria 2018

Authors and Affiliations

  • Ashraf A. Aly
    • 1
  • Essmat M. El-Sheref
    • 1
  • Aboul-Fetouh E. Mourad
    • 1
  • Alan B. Brown
    • 2
  • Stefan Bräse
    • 3
  • Momtaz E. M. Bakheet
    • 1
  • Martin Nieger
    • 4
  1. 1.Chemistry Department, Faculty of ScienceMinia UniversityEl-MiniaEgypt
  2. 2.Chemistry DepartmentFlorida Institute of TechnologyMelbourneUSA
  3. 3.Institute of Organic Chemistry, Karlsruhe Institute of TechnologyKarlsruheGermany
  4. 4.Laboratory of Inorganic Chemistry, Department of ChemistryUniversity of HelsinkiHelsinkiFinland

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