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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 go...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2010
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6259228/ https://www.ncbi.nlm.nih.gov/pubmed/20966877 http://dx.doi.org/10.3390/molecules15107353 |
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author | Imanzadeh, Gholamhassan Ahmadi, Farzaneh Zamanloo, Mohammadreza Mansoori, Yagoub |
author_facet | Imanzadeh, Gholamhassan Ahmadi, Farzaneh Zamanloo, Mohammadreza Mansoori, Yagoub |
author_sort | Imanzadeh, Gholamhassan |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-6259228 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62592282018-12-06 Tetrabutylammonium Bromide Media Aza-Michael Addition of 1,2,3,6-Tetrahydrophthalimide to Symmetrical Fumaric Esters and Acrylic Esters under Solvent-Free Conditions Imanzadeh, Gholamhassan Ahmadi, Farzaneh Zamanloo, Mohammadreza Mansoori, Yagoub Molecules Article 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. MDPI 2010-10-21 /pmc/articles/PMC6259228/ /pubmed/20966877 http://dx.doi.org/10.3390/molecules15107353 Text en © 2010 by the authors; http://creativecommons.org/licenses/by/3.0/ licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Article Imanzadeh, Gholamhassan Ahmadi, Farzaneh Zamanloo, Mohammadreza Mansoori, Yagoub Tetrabutylammonium Bromide Media Aza-Michael Addition of 1,2,3,6-Tetrahydrophthalimide to Symmetrical Fumaric Esters and Acrylic Esters under Solvent-Free Conditions |
title | Tetrabutylammonium Bromide Media Aza-Michael Addition of 1,2,3,6-Tetrahydrophthalimide to Symmetrical Fumaric Esters and Acrylic Esters under Solvent-Free Conditions |
title_full | Tetrabutylammonium Bromide Media Aza-Michael Addition of 1,2,3,6-Tetrahydrophthalimide to Symmetrical Fumaric Esters and Acrylic Esters under Solvent-Free Conditions |
title_fullStr | Tetrabutylammonium Bromide Media Aza-Michael Addition of 1,2,3,6-Tetrahydrophthalimide to Symmetrical Fumaric Esters and Acrylic Esters under Solvent-Free Conditions |
title_full_unstemmed | Tetrabutylammonium Bromide Media Aza-Michael Addition of 1,2,3,6-Tetrahydrophthalimide to Symmetrical Fumaric Esters and Acrylic Esters under Solvent-Free Conditions |
title_short | Tetrabutylammonium Bromide Media Aza-Michael Addition of 1,2,3,6-Tetrahydrophthalimide to Symmetrical Fumaric Esters and Acrylic Esters under Solvent-Free Conditions |
title_sort | tetrabutylammonium bromide media aza-michael addition of 1,2,3,6-tetrahydrophthalimide to symmetrical fumaric esters and acrylic esters under solvent-free conditions |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6259228/ https://www.ncbi.nlm.nih.gov/pubmed/20966877 http://dx.doi.org/10.3390/molecules15107353 |
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