A convenient synthesis of 5-arylidene meldrum's acid derivatives via knoevenagel condensation / Adryana Izzati Adnan, Noor Hidayah Pungot and Nur Ain Nabilah Ash’ari

Adnan, Adryana Izzati and Pungot, Noor Hidayah and Ash’ari, Nur Ain Nabilah (2021) A convenient synthesis of 5-arylidene meldrum's acid derivatives via knoevenagel condensation / Adryana Izzati Adnan, Noor Hidayah Pungot and Nur Ain Nabilah Ash’ari. Journal of Academia, 9. pp. 80-84. ISSN 2289-6368

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Abstract

A series of ten 5-arylidene Meldrum’s acid derivatives had been synthesised in excellent yield via Knoevenagel condensation. This method does not require catalyst, or any further purification. Isopropylidene malonate (2,2-dimethyl-1,3-dioxane-4,6-dione), also known as Meldrum’s acid, is utilised as a core skeleton for various kind of reactions. Meldrum’s acid has features of a peculiar ringopening sequences based on nucleophile-sensitive carbonyl functional groups at C-4 and C-6, which has made it possible for useful synthetic transformations, as well as its high acidity of met hylene hydrogen at carbon position C-5. Hence, it allows the compound to be a flexible reagent for further reaction to prepare other derivatives. Therefore, Meldrum’s acid derivatives showed high potential of biological functions, such as antibacterial, antimalarial and antioxidant activities due to the olefinic linkage which played an important role in the enhancement of antimalarial activity. Furthermore, when arylidene Meldrum’s acid transformed to epoxide, the compound showed losses of antimalarial behaviour. Additionally, this compound has unique molecules due to the high acidity of methylene hydrogen at the carbon-5 position to initiate various reactions with different functional groups. In this research, Meldrum’s acid, 3 and ten its 5-arylidene derivatives (4a-e) and (5a-e) were synthesised by using two short and efficient reaction steps. The first step involved 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% overall yield. Having Meldrum’s acid in hand, the reaction was proceeded with the Knoevenagel condensation reaction by using various functional groups, such as aryl aldehydes and aryl amines. All the synthesised compounds were characterised by using 1H and 13C spectroscopy.

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Item Type: Article
Creators:
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Adnan, Adryana Izzati
UNSPECIFIED
Pungot, Noor Hidayah
UNSPECIFIED
Ash’ari, Nur Ain Nabilah
UNSPECIFIED
Subjects: Q Science > Q Science (General) > Study and teaching > Laboratories. General works
Q Science > QH Natural history - Biology > Life > Biological control sytems
T Technology > TP Chemical technology > Chemicals > Acids
Divisions: Universiti Teknologi MARA, Negeri Sembilan
Journal or Publication Title: Journal of Academia
UiTM Journal Collections: UiTM Journal > Journal of Academia (JoA)
ISSN: 2289-6368
Volume: 9
Page Range: pp. 80-84
Item ID: 47973
Uncontrolled Keywords: convenient synthesis, 5-arylidene meldrum's acid derivatives, knoevenagel condensation
URI: https://ir.uitm.edu.my/id/eprint/47973

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47973

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