Efficient One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones via a Three-Component Biginelli Reaction
Multicomponent reactions are considered to be of increasing importance as time progresses due to the economic and environmental advantages such strategies entail. The three-component Biginelli reaction involves the combination of an aldehyde, a β-ketoester and urea to produce 3,4-dihydropyrimidin-2(...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-06-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/26/12/3753 |
| _version_ | 1827689320219148288 |
|---|---|
| author | Giovanna Bosica Fiona Cachia Riccardo De Nittis Nicole Mariotti |
| author_facet | Giovanna Bosica Fiona Cachia Riccardo De Nittis Nicole Mariotti |
| author_sort | Giovanna Bosica |
| collection | DOAJ |
| description | Multicomponent reactions are considered to be of increasing importance as time progresses due to the economic and environmental advantages such strategies entail. The three-component Biginelli reaction involves the combination of an aldehyde, a β-ketoester and urea to produce 3,4-dihydropyrimidin-2(1<i>H</i>)-ones, also known as DHPMs. The synthesis of these products is highly important due to their myriad of medicinal properties, amongst them acting as calcium channel blockers and antihypertensive and anti-inflammatory agents. In this study, silicotungstic acid supported on Ambelyst-15 was used as a heterogeneous catalyst for the Biginelli reaction under solventless conditions. Electron-poor aromatic aldehydes gave the best results. Sterically hindered β-ketoesters resulted in lower reaction yields. The reaction was carried out under heterogeneous catalysis to allow easy recovery of the product from the reaction mixture and recycling of the catalyst. The heterogeneity of the reaction was confirmed by carrying out a hot filtration test. |
| first_indexed | 2024-03-10T10:15:07Z |
| format | Article |
| id | doaj.art-e5e1f6a8e61742499dab0e787f128270 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T10:15:07Z |
| publishDate | 2021-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e5e1f6a8e61742499dab0e787f1282702023-11-22T00:54:24ZengMDPI AGMolecules1420-30492021-06-012612375310.3390/molecules26123753Efficient One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones via a Three-Component Biginelli ReactionGiovanna Bosica0Fiona Cachia1Riccardo De Nittis2Nicole Mariotti3Department of Chemistry, University of Malta, 2080 Msida, MaltaDepartment of Chemistry, University of Malta, 2080 Msida, MaltaDepartment of Chemistry, University of Malta, 2080 Msida, MaltaDepartment of Chemistry, University of Malta, 2080 Msida, MaltaMulticomponent reactions are considered to be of increasing importance as time progresses due to the economic and environmental advantages such strategies entail. The three-component Biginelli reaction involves the combination of an aldehyde, a β-ketoester and urea to produce 3,4-dihydropyrimidin-2(1<i>H</i>)-ones, also known as DHPMs. The synthesis of these products is highly important due to their myriad of medicinal properties, amongst them acting as calcium channel blockers and antihypertensive and anti-inflammatory agents. In this study, silicotungstic acid supported on Ambelyst-15 was used as a heterogeneous catalyst for the Biginelli reaction under solventless conditions. Electron-poor aromatic aldehydes gave the best results. Sterically hindered β-ketoesters resulted in lower reaction yields. The reaction was carried out under heterogeneous catalysis to allow easy recovery of the product from the reaction mixture and recycling of the catalyst. The heterogeneity of the reaction was confirmed by carrying out a hot filtration test.https://www.mdpi.com/1420-3049/26/12/3753Biginelli reactionmulticomponent reactionheterogeneous catalysissolvent-freesupported heteropoly acidone-pot |
| spellingShingle | Giovanna Bosica Fiona Cachia Riccardo De Nittis Nicole Mariotti Efficient One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones via a Three-Component Biginelli Reaction Molecules Biginelli reaction multicomponent reaction heterogeneous catalysis solvent-free supported heteropoly acid one-pot |
| title | Efficient One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones via a Three-Component Biginelli Reaction |
| title_full | Efficient One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones via a Three-Component Biginelli Reaction |
| title_fullStr | Efficient One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones via a Three-Component Biginelli Reaction |
| title_full_unstemmed | Efficient One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones via a Three-Component Biginelli Reaction |
| title_short | Efficient One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones via a Three-Component Biginelli Reaction |
| title_sort | efficient one pot synthesis of 3 4 dihydropyrimidin 2 1 i h i ones via a three component biginelli reaction |
| topic | Biginelli reaction multicomponent reaction heterogeneous catalysis solvent-free supported heteropoly acid one-pot |
| url | https://www.mdpi.com/1420-3049/26/12/3753 |
| work_keys_str_mv | AT giovannabosica efficientonepotsynthesisof34dihydropyrimidin21ihionesviaathreecomponentbiginellireaction AT fionacachia efficientonepotsynthesisof34dihydropyrimidin21ihionesviaathreecomponentbiginellireaction AT riccardodenittis efficientonepotsynthesisof34dihydropyrimidin21ihionesviaathreecomponentbiginellireaction AT nicolemariotti efficientonepotsynthesisof34dihydropyrimidin21ihionesviaathreecomponentbiginellireaction |