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

Abstract

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

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Acknowledgements

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

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CCDC 1840977 () 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 www.ccdc.cam.ac.uk/data_request/cif (DOCX 7997 kb)

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Hassan, A.A., Mohamed, N.K., Aly, A.A. et al. Convenient diastereoselective synthesis of annulated 3-substituted-(5S*,6S*,Z)-2-(2-(2,4-dinitrophenyl)hydrazono)-5,6-diphenyl-1,3-thiazinan-4-ones. Mol Divers 23, 821–828 (2019). https://doi.org/10.1007/s11030-018-09912-5

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Keywords

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