Molecules 2010, 15(10), 7353-7362; doi:10.3390/molecules15107353
Article

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

Department of Chemistry, College of Science, University of Mohaghegh Ardabili, 56199-11367, Ardabil, Iran
* Author to whom correspondence should be addressed.
Received: 19 September 2010; in revised form: 11 October 2010 / Accepted: 11 October 2010 / Published: 21 October 2010
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Abstract: 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.
Keywords: aza-Michael addition; 1,2,3,6-tetrahydrophthalimide; fumaric ester; tetrabutyl-ammonium bromide

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MDPI and ACS Style

Imanzadeh, G.; Ahmadi, F.; Zamanloo, M.; Mansoori, Y. Tetrabutylammonium Bromide Media Aza-Michael Addition of 1,2,3,6-Tetrahydrophthalimide to Symmetrical Fumaric Esters and Acrylic Esters under Solvent-Free Conditions. Molecules 2010, 15, 7353-7362.

AMA Style

Imanzadeh G, Ahmadi F, Zamanloo M, Mansoori Y. Tetrabutylammonium Bromide Media Aza-Michael Addition of 1,2,3,6-Tetrahydrophthalimide to Symmetrical Fumaric Esters and Acrylic Esters under Solvent-Free Conditions. Molecules. 2010; 15(10):7353-7362.

Chicago/Turabian Style

Imanzadeh, Gholamhassan; Ahmadi, Farzaneh; Zamanloo, Mohammadreza; Mansoori, Yagoub. 2010. "Tetrabutylammonium Bromide Media Aza-Michael Addition of 1,2,3,6-Tetrahydrophthalimide to Symmetrical Fumaric Esters and Acrylic Esters under Solvent-Free Conditions." Molecules 15, no. 10: 7353-7362.

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