Synthesis of (4<i>H</i>)‐Imidazol‐4‐ones from <i>α</i>‐Amino Acids, and their Antioxidant Activities using Electron Transfer Methods

Abstract A novel series of (4 H )‐imidazol‐4‐ones, designated as compounds 5(a–l) , were synthesized from phenylalanine and tyrosine. This synthesis involved derivatization of amino acids with phenylacetyl chloride, followed by cyclocondensation with aromatic amines using PCl 3 and a deep eutectic solvent as both catalyst and solvent. Amide intermediates were first produced via the Schotten‐Baumann reaction. These intermediates then underwent cyclization in the presence of PCl 3 and deep‐eutectic solvent, leading to the formation of imidazolones as potent antioxidants. The newly synthesized compounds were evaluated for their antioxidant activities using several electron transfer‐based assays, including DPPH, ABTS, FRAP, and CUPRAC. Among the tested compounds, compound 5 i exhibited excellent antioxidant activity compared to the standard reference drugs, ascorbic acid and Trolox.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-02-18
DOI
https://doi.org/10.1002/ejoc.202401449
Citations
1
Primary Topic
Synthesis and Reactions of Organic Compounds
Type
article
Field-Weighted Citation Impact
0.94
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article

Synthesis of (4H)‐Imidazol‐4‐ones from α‐Amino Acids, and their Antioxidant Activities using Electron Transfer Methods

Mayanglambam Maneeta Devi, Thokchom Prasanta Singh, Thangjam Linda Devi, Keisham Subharani Devi
1 citations
European Journal of Organic Chemistry
Synthesis and Reactions of Organic Compounds
0.94
article

Synthesis of (4H)‐Imidazol‐4‐ones from α‐Amino Acids, and their Antioxidant Activities using Electron Transfer Methods

Mayanglambam Maneeta Devi, Thokchom Prasanta Singh, Thangjam Linda Devi, Keisham Subharani Devi
article en
1 citations

Abstract

Abstract A novel series of (4 H )‐imidazol‐4‐ones, designated as compounds 5(a–l) , were synthesized from phenylalanine and tyrosine. This synthesis involved derivatization of amino acids with phenylacetyl chloride, followed by cyclocondensation with aromatic amines using PCl 3 and a deep eutectic solvent as both catalyst and solvent. Amide intermediates were first produced via the Schotten‐Baumann reaction. These intermediates then underwent cyclization in the presence of PCl 3 and deep‐eutectic solvent, leading to the formation of imidazolones as potent antioxidants. The newly synthesized compounds were evaluated for their antioxidant activities using several electron transfer‐based assays, including DPPH, ABTS, FRAP, and CUPRAC. Among the tested compounds, compound 5 i exhibited excellent antioxidant activity compared to the standard reference drugs, ascorbic acid and Trolox.

European Journal of Organic ChemistryVol. 28(15)
Manipur University (IN)
Openalex Percentile: Top 29%
Synthesis and Reactions of Organic Compounds
0.94
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Synthesis of (4<i>H</i>)‐Imidazol‐4‐ones from <i>α</i>‐Amino Acids, and their Antioxidant Activities using Electron Transfer Methods — Mayanglambam Maneeta Devi, Thokchom Prasanta Singh, et al. · European Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS