Regioselective and stereoselective synthesis of epithiomethanoiminoindeno[1,2-b]furan-3-carbonitrile: heterocyclic [3.3.3]propellanes

Molecular Diversity volume 25, pages99–108(2021)Cite this article

Abstract

Synthesis of heteropropellanes in one step: the reaction between dicyanomethylene-1,3-indanedione (CNIND) and N-substituted-2-(2,4-dinitrophenyl)hydrazinecarbothioamides, furnished (3aR,8bS,Z)-2-amino-9-substituted-10-(2-(2,4-dinitrophenyl)hydrazono)-4-oxo-4H-3a,8b-(epithiomethanoimino)indeno[1,2-b]furan-3-carbonitrile as a type of (2,4-dinitrophenyl)hydrazono[3.3.3]propellanes in good yields as single diastereomers. Structure determination and confirmation of the synthesized products have been achieved using various and modern spectroscopic techniques such as IR, NMR (1H NMR and 13C NMR), mass spectrometry, as well as X-ray crystal analysis. The X-ray structure data cleared that the molecule of 7a was crystalized as monoclinic, space group C2/c (no.15).

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Acknowledgements

Alaa A. Hassan is indebted to the AvH-Foundation for the donation of a Shimadzu 408 IR instrument.

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Affiliations

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

    Alaa A. Hassan, Nasr K. Mohamed, Ashraf A. Aly & Hendawy N. Tawfeek

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

    Stefan Bräse

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

    Stefan Bräse

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

    Martin Nieger

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  1. Alaa A. Hassan
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Hassan, A.A., Mohamed, N.K., Aly, A.A. et al. Regioselective and stereoselective synthesis of epithiomethanoiminoindeno[1,2-b]furan-3-carbonitrile: heterocyclic [3.3.3]propellanes. Mol Divers 25, 99–108 (2021). https://doi.org/10.1007/s11030-019-10027-8

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Keywords

  • Annulated compounds
  • Heterocyclization
  • Imine-enamine tautomerism
  • Nucleophilic addition
  • Furothiazolo[3.3.3]propellanes
  • Thiosemicarbazides