Tetrabutylammonium bromide media aza-Michael addition of 1,2,3,6-tetrahydrophthalimide to symmetrical fumaric esters and acrylic esters under solvent-free conditions.
The aza-Michael addition of 1,2,3,6-tetrahydrophthalimide with symmetrical fumaric esters has been performed efficiently in a solvent-free system at 100 °C and using 1,4-diazabicyclo[2.2.2]octane (DABCO) as a base in the presence of tetrabutylammonium bromide (TBAB). The products were obtained in good to high yields within 2.5-7.0 h. This reaction worked well on linear alkyl fumarates and was not effective with nonlinear alkyl fumarates. Although the reaction was also applicable to acrylates such as n-butyl acrylate, methacrylates and crotonates were not suitable Michael acceptors for this reaction.
Department of Chemistry, College of Science, University of Mohaghegh Ardabili, 56199-11367 Ardabil, Iran. Imanzad2000@yahoo.com
Gholamhassan
G
Imanzadeh
Farzaneh
F
Ahmadi
Mohammadreza
M
Zamanloo
Yagoub
Y
Mansoori
D000179:Acrylates / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D002215:Captan / Q000737:chemistry*; D003902:Detergents / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D005650:Fumarates / Q000737:chemistry*; D015394:Molecular Structure; D010797:Phthalimides / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
D000179:Acrylates; D001372:Aza Compounds; D003902:Detergents; D004952:Esters; D005650:Fumarates; D010797:Phthalimides; D000644:Quaternary Ammonium Compounds; D012997:Solvents; C009417:tetrahydrophthalimide; C009405:tetrabutylammonium; D002215:Captan