A CONVENIENT SYNTHESIS OF 5-ARYLIDENE MELDRUM'S ACID DERIVATIVES VIA KNOEVENGAL CONDENSATION WITH VARIOUS FUNCTIONAL GROUPS

  • Noor Hidayah Pungot Dr
  • Adryana Izzati Adnan Izzati Adnan Universiti Teknologi MARA (UiTM), Shah Alam
  • Nur Ain Nabilah Ash'ari Universiti Teknologi MARA (UiTM), Shah Alam

Abstract

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.


 

Published
2021-04-30
How to Cite
PUNGOT, Noor Hidayah; ADNAN, Adryana Izzati Adnan Izzati; ASH'ARI, Nur Ain Nabilah. A CONVENIENT SYNTHESIS OF 5-ARYLIDENE MELDRUM'S ACID DERIVATIVES VIA KNOEVENGAL CONDENSATION WITH VARIOUS FUNCTIONAL GROUPS. Journal of Academia, [S.l.], v. 9, n. 1, p. 80-84, apr. 2021. ISSN 2289-6368. Available at: <https://myjms.mohe.gov.my/index.php/joa/article/view/11132>. Date accessed: 20 may 2024.
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