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. 2019 Nov;23(4):821-828. doi: 10.1007/s11030-018-09912-5. Epub 2019 Jan 3.

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.

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

MeSH terms

  • Crystallography, X-Ray
  • Cyclopropanes / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Semicarbazides / chemistry
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry

Substances

  • Cyclopropanes
  • Semicarbazides
  • Thiazoles
  • thiosemicarbazide
  • diphenylcyclopropenone