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Reactive intermediates in the reaction of hydrazinecarbothioamides with 2-(bis(methylthio)methylene)malononitrile and ethyl 2-cyano-3,3-bis(methylthio)acrylate

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Abstract

The reaction of N-substituted hydrazinecarbothioamides with both 2-(bis(methylthio)methylene)malononitrile and ethyl 2-cyano-3,3-bis(methylthio)acrylate afforded various heterocyclic rings such as 5-amino-4-cyano-3-(methylthio)-N-phenyl-1H-pyrazole-1-carbothioamide, 5-amino-3-(methylthio)-1H-pyrazole-4-carbonitrile, 4-substituted-3-(substituted amino)-1H-1,2,4-triazole-5(4H)-thione, ethyl 5-amino-3-(methylthio)-1-(substituted carbamothioyl)-1H-pyrazole-4-carboxylate, and (Z)-ethyl 2-cyano-2-(5-(substituted amino)-1,3,4-thiadiazol-2(3H)-ylidene)acetate. However, under gentle heating, the reaction of the same starting substances behaved differently. The structure of the obtained products was fully characterized using different spectral techniques including infrared (IR), nuclear magnetic resonance (NMR), and mass spectrometry (MS) together with elemental analyses as well as single-crystal X-ray diffraction analysis.

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Authors and Affiliations

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

    Ashraf A. Aly, Alaa A. Hassan, Nasr K. Mohamed, Kamal M. El-Shaieb & Maysa M. Makhlouf

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

    Stefan Bräse

  3. Department of Chemistry, University of Helsinki, P.O. Box55, A. I. Virtasen Aukio 1, 00014, Helsinki, Finland

    Martin Nieger

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  1. Ashraf A. Aly
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  2. Alaa A. Hassan
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  4. Kamal M. El-Shaieb
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Aly, A.A., Hassan, A.A., Mohamed, N.K. et al. Reactive intermediates in the reaction of hydrazinecarbothioamides with 2-(bis(methylthio)methylene)malononitrile and ethyl 2-cyano-3,3-bis(methylthio)acrylate. Res Chem Intermed 45, 613–631 (2019). https://doi.org/10.1007/s11164-018-3633-4

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