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1,3-Bis(carboxymethyl)imidazolium Chloride as a Sustainable, Recyclable, and Metal-Free Ionic Catalyst for the Biginelli Multicomponent Reaction in Neat Condition
[Image: see text] A simple and novel methodology has been developed for the synthesis of 1,3-bis(carboxymethyl)imidazolium chloride [BCMIM][Cl] salt. The ionic salt [BCMIM][Cl] catalyzed the reaction among arylaldehydes; the substituted 1,3-dicarbonyl compounds and urea/thiourea at 80 °C with 5 mol...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2021
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8515400/ https://www.ncbi.nlm.nih.gov/pubmed/34660965 http://dx.doi.org/10.1021/acsomega.1c02976 |
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author | Madivalappa Davanagere, Prabhakara Maiti, Barnali |
author_facet | Madivalappa Davanagere, Prabhakara Maiti, Barnali |
author_sort | Madivalappa Davanagere, Prabhakara |
collection | PubMed |
description | [Image: see text] A simple and novel methodology has been developed for the synthesis of 1,3-bis(carboxymethyl)imidazolium chloride [BCMIM][Cl] salt. The ionic salt [BCMIM][Cl] catalyzed the reaction among arylaldehydes; the substituted 1,3-dicarbonyl compounds and urea/thiourea at 80 °C with 5 mol % under neat condition provided the substituted dihydropyrimidin-2(1H)-one/thiones in the synthesis step with yields of up to 96%. In addition, we synthesized the commercially available drug Monastrol by employing this methodology. The new synthesis method employs the benefits of a broad substrate scope, short reaction time, and high atom economy along with low catalyst loading in neat conditions, and is devoid of chromatographic purification. The ionic salt [BCMIM][Cl] was recycled and reused up to six cycles without substantial damage of its catalytic efficiency. |
format | Online Article Text |
id | pubmed-8515400 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-85154002021-10-15 1,3-Bis(carboxymethyl)imidazolium Chloride as a Sustainable, Recyclable, and Metal-Free Ionic Catalyst for the Biginelli Multicomponent Reaction in Neat Condition Madivalappa Davanagere, Prabhakara Maiti, Barnali ACS Omega [Image: see text] A simple and novel methodology has been developed for the synthesis of 1,3-bis(carboxymethyl)imidazolium chloride [BCMIM][Cl] salt. The ionic salt [BCMIM][Cl] catalyzed the reaction among arylaldehydes; the substituted 1,3-dicarbonyl compounds and urea/thiourea at 80 °C with 5 mol % under neat condition provided the substituted dihydropyrimidin-2(1H)-one/thiones in the synthesis step with yields of up to 96%. In addition, we synthesized the commercially available drug Monastrol by employing this methodology. The new synthesis method employs the benefits of a broad substrate scope, short reaction time, and high atom economy along with low catalyst loading in neat conditions, and is devoid of chromatographic purification. The ionic salt [BCMIM][Cl] was recycled and reused up to six cycles without substantial damage of its catalytic efficiency. American Chemical Society 2021-10-01 /pmc/articles/PMC8515400/ /pubmed/34660965 http://dx.doi.org/10.1021/acsomega.1c02976 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Madivalappa Davanagere, Prabhakara Maiti, Barnali 1,3-Bis(carboxymethyl)imidazolium Chloride as a Sustainable, Recyclable, and Metal-Free Ionic Catalyst for the Biginelli Multicomponent Reaction in Neat Condition |
title | 1,3-Bis(carboxymethyl)imidazolium Chloride as a Sustainable,
Recyclable, and Metal-Free Ionic Catalyst for the Biginelli Multicomponent
Reaction in Neat Condition |
title_full | 1,3-Bis(carboxymethyl)imidazolium Chloride as a Sustainable,
Recyclable, and Metal-Free Ionic Catalyst for the Biginelli Multicomponent
Reaction in Neat Condition |
title_fullStr | 1,3-Bis(carboxymethyl)imidazolium Chloride as a Sustainable,
Recyclable, and Metal-Free Ionic Catalyst for the Biginelli Multicomponent
Reaction in Neat Condition |
title_full_unstemmed | 1,3-Bis(carboxymethyl)imidazolium Chloride as a Sustainable,
Recyclable, and Metal-Free Ionic Catalyst for the Biginelli Multicomponent
Reaction in Neat Condition |
title_short | 1,3-Bis(carboxymethyl)imidazolium Chloride as a Sustainable,
Recyclable, and Metal-Free Ionic Catalyst for the Biginelli Multicomponent
Reaction in Neat Condition |
title_sort | 1,3-bis(carboxymethyl)imidazolium chloride as a sustainable,
recyclable, and metal-free ionic catalyst for the biginelli multicomponent
reaction in neat condition |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8515400/ https://www.ncbi.nlm.nih.gov/pubmed/34660965 http://dx.doi.org/10.1021/acsomega.1c02976 |
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