A CONVENIENT SYNTHESIS OF 5-ARYLIDENE MELDRUM'S ACID DERIVATIVES VIA KNOEVENGAL CONDENSATION WITH VARIOUS FUNCTIONAL GROUPS
A series of ten arylidene Meldrum’s acid derivatives have been synthesized in excellent yield via Knoevenagel condensation. This efficient synthetic method does not require catalyst and further purification step. Isopropylidene malonate (2,2-dimethyl-1,3-dioxane-4,6-dione), also known as Meldrum’s a...
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| Format: | Article |
| Language: | English |
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Universiti Teknologi MARA, Negeri Sembilan
2021-04-01
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| Series: | Journal of Academia |
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| Online Access: | https://myjms.mohe.gov.my/index.php/joa/article/view/11132 |
| _version_ | 1797202325944664064 |
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| author | Adryana Izzati Adnan Noor Hidayah Pungot Nur Ain Nabilah Ash’ari |
| author_facet | Adryana Izzati Adnan Noor Hidayah Pungot Nur Ain Nabilah Ash’ari |
| author_sort | Adryana Izzati Adnan |
| collection | DOAJ |
| description | A series of ten arylidene Meldrum’s acid derivatives have been synthesized in excellent yield via Knoevenagel condensation. This efficient synthetic method does not require catalyst and further purification step. Isopropylidene malonate (2,2-dimethyl-1,3-dioxane-4,6-dione), also known as Meldrum’s acid is present as the core skeleton in various kind of reactions. Meldrum’s acid features a peculiar ring-opening mechanism that allows the compound to be a flexible reagent and enables the molecule to further synthesize its derivatives. Therefore, Meldrum’s acid derivatives showed high potential of biological properties such as antibacterial, antimalarial and antioxidant activity. This compound is also considered as a unique molecule with a complex history due to its structure that has been mistakenly assigned by researchers, as well as its high acidity of methylene hydrogen at the carbon of C-5 position. In this research, Meldrum’s acid and its 5-arylidene derivatives were synthesized by using two short and efficient reaction steps. The first step involves the condensation of malonic acid, 1 with acetone, 2 in acetic anhydride and acid via one-pot reaction to give Meldrum’s acid, 3 in 50% yield. Having Meldrum’s acid in hand, the reaction proceeded with the Knoevengal condensation reaction using diverse functional groups such as aryl aldehydes and aryl amines in excellent yield. All the synthesized compounds were characterized using 1H and 13C NMR spectroscopy. |
| first_indexed | 2024-04-24T08:01:39Z |
| format | Article |
| id | doaj.art-7b95fcde63ed4bbebfae1a198e83d18f |
| institution | Directory Open Access Journal |
| issn | 2289-6368 |
| language | English |
| last_indexed | 2024-04-24T08:01:39Z |
| publishDate | 2021-04-01 |
| publisher | Universiti Teknologi MARA, Negeri Sembilan |
| record_format | Article |
| series | Journal of Academia |
| spelling | doaj.art-7b95fcde63ed4bbebfae1a198e83d18f2024-04-17T16:36:02ZengUniversiti Teknologi MARA, Negeri SembilanJournal of Academia2289-63682021-04-01918084A CONVENIENT SYNTHESIS OF 5-ARYLIDENE MELDRUM'S ACID DERIVATIVES VIA KNOEVENGAL CONDENSATION WITH VARIOUS FUNCTIONAL GROUPSAdryana Izzati Adnan0Noor Hidayah Pungot1Nur Ain Nabilah Ash’ari2Faculty of Applied Sciences, School of Chemistry and Environment, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Selangor, MalaysiaOrganic Synthesis Laboratory, Institute of Science, Universiti Teknologi MARA, Puncak Alam Campus, 43200 Bandar Puncak Alam, Selangor, Malaysia.Organic Synthesis Laboratory, Institute of Science, Universiti Teknologi MARA, Puncak Alam Campus, 43200 Bandar Puncak Alam, Selangor, Malaysia.A series of ten arylidene Meldrum’s acid derivatives have been synthesized in excellent yield via Knoevenagel condensation. This efficient synthetic method does not require catalyst and further purification step. Isopropylidene malonate (2,2-dimethyl-1,3-dioxane-4,6-dione), also known as Meldrum’s acid is present as the core skeleton in various kind of reactions. Meldrum’s acid features a peculiar ring-opening mechanism that allows the compound to be a flexible reagent and enables the molecule to further synthesize its derivatives. Therefore, Meldrum’s acid derivatives showed high potential of biological properties such as antibacterial, antimalarial and antioxidant activity. This compound is also considered as a unique molecule with a complex history due to its structure that has been mistakenly assigned by researchers, as well as its high acidity of methylene hydrogen at the carbon of C-5 position. In this research, Meldrum’s acid and its 5-arylidene derivatives were synthesized by using two short and efficient reaction steps. The first step involves the condensation of malonic acid, 1 with acetone, 2 in acetic anhydride and acid via one-pot reaction to give Meldrum’s acid, 3 in 50% yield. Having Meldrum’s acid in hand, the reaction proceeded with the Knoevengal condensation reaction using diverse functional groups such as aryl aldehydes and aryl amines in excellent yield. All the synthesized compounds were characterized using 1H and 13C NMR spectroscopy.https://myjms.mohe.gov.my/index.php/joa/article/view/11132biological activitiesknoevenagel condensationmeldrum’s acidnmr spectroscopyone-pot reaction |
| spellingShingle | Adryana Izzati Adnan Noor Hidayah Pungot Nur Ain Nabilah Ash’ari A CONVENIENT SYNTHESIS OF 5-ARYLIDENE MELDRUM'S ACID DERIVATIVES VIA KNOEVENGAL CONDENSATION WITH VARIOUS FUNCTIONAL GROUPS Journal of Academia biological activities knoevenagel condensation meldrum’s acid nmr spectroscopy one-pot reaction |
| title | A CONVENIENT SYNTHESIS OF 5-ARYLIDENE MELDRUM'S ACID DERIVATIVES VIA KNOEVENGAL CONDENSATION WITH VARIOUS FUNCTIONAL GROUPS |
| title_full | A CONVENIENT SYNTHESIS OF 5-ARYLIDENE MELDRUM'S ACID DERIVATIVES VIA KNOEVENGAL CONDENSATION WITH VARIOUS FUNCTIONAL GROUPS |
| title_fullStr | A CONVENIENT SYNTHESIS OF 5-ARYLIDENE MELDRUM'S ACID DERIVATIVES VIA KNOEVENGAL CONDENSATION WITH VARIOUS FUNCTIONAL GROUPS |
| title_full_unstemmed | A CONVENIENT SYNTHESIS OF 5-ARYLIDENE MELDRUM'S ACID DERIVATIVES VIA KNOEVENGAL CONDENSATION WITH VARIOUS FUNCTIONAL GROUPS |
| title_short | A CONVENIENT SYNTHESIS OF 5-ARYLIDENE MELDRUM'S ACID DERIVATIVES VIA KNOEVENGAL CONDENSATION WITH VARIOUS FUNCTIONAL GROUPS |
| title_sort | convenient synthesis of 5 arylidene meldrum s acid derivatives via knoevengal condensation with various functional groups |
| topic | biological activities knoevenagel condensation meldrum’s acid nmr spectroscopy one-pot reaction |
| url | https://myjms.mohe.gov.my/index.php/joa/article/view/11132 |
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