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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

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...

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Main Authors: Adnan, Adryana Izzati, Pungot, Noor Hidayah, Ash’ari, Nur Ain Nabilah
Format: Article
Language:English
Published: Universiti Teknologi MARA, Negeri Sembilan 2021
Subjects:
Laboratories. General works
Biological control sytems
Acids
Online Access:http://ir.uitm.edu.my/id/eprint/47973/1/47973.pdf
http://ir.uitm.edu.my/id/eprint/47973/
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spelling my.uitm.ir.479732021-06-22T04:31:46Z http://ir.uitm.edu.my/id/eprint/47973/ 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 Pungot, Noor Hidayah Ash’ari, Nur Ain Nabilah Laboratories. General works Biological control sytems Acids 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. Universiti Teknologi MARA, Negeri Sembilan 2021 Article PeerReviewed text en http://ir.uitm.edu.my/id/eprint/47973/1/47973.pdf ID47973 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
institution Universiti Teknologi Mara
building Tun Abdul Razak Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Teknologi Mara
content_source UiTM Institutional Repository
url_provider http://ir.uitm.edu.my/
language English
topic Laboratories. General works
Biological control sytems
Acids
spellingShingle Laboratories. General works
Biological control sytems
Acids
Adnan, Adryana Izzati
Pungot, Noor Hidayah
Ash’ari, Nur Ain Nabilah
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
description 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.
format Article
author Adnan, Adryana Izzati
Pungot, Noor Hidayah
Ash’ari, Nur Ain Nabilah
author_facet Adnan, Adryana Izzati
Pungot, Noor Hidayah
Ash’ari, Nur Ain Nabilah
author_sort Adnan, Adryana Izzati
title 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
title_short 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_sort convenient synthesis of 5-arylidene meldrum's acid derivatives via knoevenagel condensation / adryana izzati adnan, noor hidayah pungot and nur ain nabilah ash’ari
publisher Universiti Teknologi MARA, Negeri Sembilan
publishDate 2021
url http://ir.uitm.edu.my/id/eprint/47973/1/47973.pdf
http://ir.uitm.edu.my/id/eprint/47973/
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score 13.211869

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