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

  • Alaa A. HassanEmail author
  • Ashraf A. Aly
  • Nasr K. Mohamed
  • Kamal M. El-Shaieb
  • Maysa M. Makhlouf
  • Stefan Bräse
  • Martin Nieger
  • Alan B. Brown


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.


N-Substituted alkenylidene hydrazinecarbothioamides Tetracyanoethylene Stereoselective 1,3-thiazole derivatives Donor–acceptor interaction X-ray crystallography 



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

Supplementary material

11164_2019_4051_MOESM1_ESM.docx (149 kb)
Supplementary material 1 (DOCX 149 kb)


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Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Chemistry Department, Faculty of ScienceMinia UniversityEl-MiniaEgypt
  2. 2.Institute of Organic Chemistry, Karlsruhe Institute of TechnologyKarlsruheGermany
  3. 3.Institute of Toxicology and GeneticsEggenstein-LeopoldshafenGermany
  4. 4.Department of ChemistryUniversity of HelsinkiHelsinkiFinland
  5. 5.Program, Florida Institute oMelbourneUSA

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