Next Article in Journal
Chemometric Studies on Natural Products as Potential Inhibitors of the NADH Oxidase from Trypanosoma cruzi Using the VolSurf Approach
Previous Article in Journal
Plant Phenolics: Extraction, Analysis and Their Antioxidant and Anticancer Properties
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

* , ,  and
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 / Revised: 11 October 2010 / Accepted: 11 October 2010 / Published: 21 October 2010
Download PDF [184 KB, uploaded 18 June 2014]

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 aza-Michael addition; 1,2,3,6-tetrahydrophthalimide; fumaric ester; tetrabutyl-ammonium bromide
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert