Three-component reaction between triphenylphosphine, dialkyl acetylenedicarboxylates and urea or N-methylurea

Mol Divers. 2006 Feb;10(1):23-7. doi: 10.1007/s11030-006-8696-2.

Abstract

The stabilized phosphoranes, obtained from the three-component reaction between dialkyl acetylenedicarboxylates and urea or N-methylurea in the presence of triphenylphosphine, undergo a smooth reaction in boiling toluene to produce iminophosphoranes in good yields. Under the same reaction conditions, the phosphorane obtained from N-methylurea and dimethyl acetylenedicarboxylate yields methyl 1-methyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylate.

MeSH terms

  • Acetylene / analogs & derivatives*
  • Acetylene / chemistry
  • Alkynes
  • Methylurea Compounds / chemistry*
  • Organophosphorus Compounds / chemistry*
  • Phosphoranes / chemical synthesis*
  • Phosphoranes / chemistry
  • Toluene
  • Urea / chemistry

Substances

  • Alkynes
  • Methylurea Compounds
  • Organophosphorus Compounds
  • Phosphoranes
  • triphenylphosphine
  • Toluene
  • acetylenedicarboxylic acid dimethyl ester
  • Urea
  • Acetylene
  • methylurea