Three-component reaction between triphenylphosphine, dialkyl acetylenedicarboxylates and urea or N-methylurea.
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.
Yavari
Issa
I
Department of Chemistry, Tarbiat Modarres University, PO Box 14115-175, Tehran, Iran. yavarisa@modares.ac.ir
Zabarjad-Shiraz
Nader
N
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D000480:Alkynes; D008782:Methylurea Compounds / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010753:Phosphoranes / Q000138:chemical synthesis* / Q000737:chemistry; D014050:Toluene; D014508:Urea / Q000737:chemistry
D000480:Alkynes; D008782:Methylurea Compounds; D009943:Organophosphorus Compounds; D010753:Phosphoranes; C061896:triphenylphosphine; D014050:Toluene; C022918:acetylenedicarboxylic acid dimethyl ester; D014508:Urea; D000114:Acetylene; C002352:methylurea