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Research on Chemical Intermediates

, Volume 45, Issue 2, pp 613–631 | Cite as

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

  • Ashraf A. AlyEmail author
  • Alaa A. Hassan
  • Nasr K. Mohamed
  • Kamal M. El-Shaieb
  • Maysa M. Makhlouf
  • Stefan Bräse
  • Martin Nieger
Article
  • 68 Downloads

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.

Graphical abstract

Keywords

N-substituted hydrazinecarbothioamides 2-(Bis(methylthio)methylene)malononitriles Reactive intermediates Various heterocycles X-ray structure analyses 

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Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  • Ashraf A. Aly
    • 1
    Email author
  • Alaa A. Hassan
    • 1
  • Nasr K. Mohamed
    • 1
  • Kamal M. El-Shaieb
    • 1
  • Maysa M. Makhlouf
    • 1
  • Stefan Bräse
    • 2
  • Martin Nieger
    • 3
  1. 1.Chemistry Department, Faculty of ScienceMinia UniversityEl-MiniaEgypt
  2. 2.Institute of Organic ChemistryKarlsruhe Institute of TechnologyKarlsruheGermany
  3. 3.Department of ChemistryUniversity of HelsinkiHelsinkiFinland

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