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Reactivity of N-substituted alkenylidene hydrazinecarbothioamides toward tetracyanoethylene, an efficient synthesis stereoselective 1,3-thiazole compounds

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Abstract

The reaction between N-substituted alkenylidene hydrazinecarbothioamides and two molar amounts of tetracyanoethylene (TCNE) in anhydrous THF at room temperature without using any catalyst affords (Z)-4-amino-3-((Z)substituted amino)-2-(substituted imino)-2,3-dihydrothiazole-5-carbonitriles and (Z)-(4-amino-5-cyano-thiazol-2(3H)-ylidene)carbonhydrazonoyl dicyanides. Rationales for these transformations are presented. The structures of the obtained products were confirmed via single-crystal X-ray analyses.

Graphic Abstract

Here, we synthesize (Z)-4-amino-3-amino-2-imino-2,3-dihydrothiazole-5-carbonitriles and (Z)-(4-amino-5-cyano-thiazol-2(3H)-ylidene)carbonhydrazonoyl dicyanides from the reaction of N-substituted alkenylidene hydrazinecarbothioamides with (TCNE) in anhydrous THF at room temperature without using any catalyst.

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Acknowledgements

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

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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, Kamal M. El-Shaieb & Maysa M. Makhlouf

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

    Stefan Bräse

  3. Institute of Toxicology and Genetics, Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany

    Stefan Bräse

  4. Department of Chemistry, University of Helsinki, A. I. Virtasen aukio 1, P.O. Box 55, 00014, Helsinki, Finland

    Martin Nieger

  5. Program, Florida Institute o, Melbourne, FL, 32901, USA

    Alan B. Brown

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  1. Alaa A. Hassan
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Correspondence to Alaa A. Hassan.

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Hassan, A.A., Aly, A.A., Mohamed, N.K. et al. Reactivity of N-substituted alkenylidene hydrazinecarbothioamides toward tetracyanoethylene, an efficient synthesis stereoselective 1,3-thiazole compounds. Res Chem Intermed 46, 1571–1585 (2020). https://doi.org/10.1007/s11164-019-04051-4

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