Convenient diastereoselective synthesis of annulated 3-substituted-(5S*,6S*,Z)-2-(2-(2,4-dinitrophenyl)hydrazono)-5,6-diphenyl-1,3-thiazinan-4-ones

  • Alaa A. HassanEmail author
  • Nasr K. Mohamed
  • Ashraf A. Aly
  • Hendawy N. Tawfeek
  • Henning Hopf
  • Stefan Bräse
  • Martin Nieger
Original Article


Racemic 2-(2,4-dinitrophenyl)hydrazono)-5,6-diphenyl-1,3-thiazinan-4-ones and (Z)-N′-(2,4-dinitrophenyl)-2,3-diphenylacrylohydrazide were formed during the diastereoselective reaction between 4-substituted 1-(2,4-dinitrophenyl)thiosemicarbazides and 2,3-diphenylcycloprop-2-enone under refluxing ethanol. The structures of the synthesized compounds were confirmed by single-crystal X-ray analyses.

Graphical abstract


1,3-Thiazinan-4-ones Substituted 2,3-diphenylacrylohydrazide (2,4-Dinitrophenyl)-4-substituted thiosemicarbazides 2,3-Diphenylcyclopropenone Annulated compounds 



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

Supplementary material

11030_2018_9912_MOESM1_ESM.docx (7.8 mb)
CCDC 1840977 (7a) and 1840978 (8) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via (DOCX 7997 kb)


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Copyright information

© Springer Nature Switzerland AG 2019

Authors and Affiliations

  1. 1.Chemistry Department, Faculty of ScienceMinia UniversityEl-MiniaEgypt
  2. 2.Institut für Organische ChemieTechnische Universität BraunschweigBrunswickGermany
  3. 3.Institute of Organic ChemistryKarlsruhe Institute of TechnologyKarlsruheGermany
  4. 4.Department of ChemistryUniversity of HelsinkiHelsinkiFinland

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