Tetrabutylammonium Bromide Media Aza-Michael Addition of 1,2,3,6-Tetrahydrophthalimide to Symmetrical Fumaric Esters and Acrylic Esters under Solvent-Free Conditions

Molecules

Gholamhassan Imanzadeh¹  Farzaneh Ahmadi¹  Mohammadreza Zamanloo¹ 

[1] Department of Chemistry, College of Science, University of Mohaghegh Ardabili, 56199-11367, Ardabil, Iran

关键词: aza-Michael addition;    1;    2;    3;    6-tetrahydrophthalimide;    fumaric ester;    tetrabutyl-ammonium bromide;   

DOI  :  10.3390/molecules15107353

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.