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Tetracyanoethylene as a building block in the facile synthesis of heteroyl-tetrasubstituted thiazoles

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Abstract

The transformation of N-substituted 2-heteroylthiosemicarbazides to N-(2-substituted imino)-4-amino-5-cyanothiazol-3(2H)-3-yl)-heteroyl-2-carboxamides was achieved via the reaction with tetracyanoethylene, which is used as a building block in this transformation. The structures of the products have been confirmed unambiguously by single-crystal X-ray structure analysis. A rationale for the formation of the products is presented.

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Acknowledgements

Alaa A. Hassan is indebted to the AvH-Foundation for the donation of a Shimadzu 408 IR instrument. The authors also thank Egyptian Mission, Ministry of higher education, Egypt for its financial support to Mrs. Lamiaa E. Abd El-Haleem during her accommodation at the Karlsruhe Institute für Technology, Karlsruhe, Germany.

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Authors and Affiliations

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

    Alaa A. Hassan, Ashraf A. Aly, Nasr K. Mohamed & Lamiaa E. Abd El-Haleem

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

    Lamiaa E. Abd El-Haleem & Stefan Bräse

  3. 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

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

    Martin Nieger

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  1. Alaa A. Hassan
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  2. Ashraf A. Aly
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  3. Nasr K. Mohamed
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  4. Lamiaa E. Abd El-Haleem
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  5. Stefan Bräse
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  6. Martin Nieger
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Correspondence to Alaa A. Hassan.

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Hassan, A.A., Aly, A.A., Mohamed, N.K. et al. Tetracyanoethylene as a building block in the facile synthesis of heteroyl-tetrasubstituted thiazoles. Monatsh Chem 151, 1425–1431 (2020). https://doi.org/10.1007/s00706-020-02669-4

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  • DOI: https://doi.org/10.1007/s00706-020-02669-4

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