Iodine-mediated Unique Intramolecular Rearrangement of Amide to Nitrile in Thiophenes and their Antioxidant Potential Studies

Mamatha Mahesha; Kempegowda Mantelingu; Nagarakere C. Sandhya; Bettadapura R. Nuthan; Shamanth Sadashivamurthy; Bilagumba T. Sridhar; Sreedharamurthy Satish

doi:10.2174/0115701786357751250507110749

ISSN: 1570-1786
E-ISSN: 1875-6255

Iodine-mediated Unique Intramolecular Rearrangement of Amide to Nitrile in Thiophenes and their Antioxidant Potential Studies
Authors: Mamatha Mahesha^1,2, Kempegowda Mantelingu¹, Nagarakere C. Sandhya³, Bettadapura R. Nuthan⁴, Shamanth Sadashivamurthy¹, Bilagumba T. Sridhar⁵ and Sreedharamurthy Satish⁴
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¹ DOS in Chemistry, University of Mysore, Mysuru, Karnataka, 570006, India ; ² Maharani’s Science College for Women, Mysuru, Karnataka, 570005, India ; ³ Department of Chemistry, Mysore University School of Engineering, Manasagangotri, University of Mysore, Mysuru, Karnataka, 570006, India ; ⁴ DOS in Microbiology, Manasagangotri, University of Mysore, Mysuru, Karnataka, 570006, India ; ⁵ Department of Chemistry, Maharani Science College for Women, Maharani Cluster University, Bangalore, Karnataka, 560001, India
Source: Letters in Organic Chemistry, Volume 22, Issue 11, Nov 2025, p. 837 - 845
DOI: https://doi.org/10.2174/0115701786357751250507110749
- Received: 04 Nov 2024
- Accepted: 11 Mar 2025
- Available online: 01 Nov 2025

Abstract

The current work describes a unique iodine-mediated intra-molecular rearrangement of amide to nitrile and thiourea to urea, which took place simultaneously in thiophenes. The thiophenes having amide and amine groups at the adjacent positions were prepared via the Gewald reaction and subsequently treated with isothiocyanates in the presence of molecular iodine to get 1-(3-cyanothiophen-2-yl)-3-phenylureas in good yields. The synthesized compounds are of particular interest both chemically and biologically, as they contain thiophene, urea, and nitrile moieties in a single molecule. Many thiophene derivatives have been reported to exhibit antioxidant properties. Hence, the synthesized molecules were screened for their antioxidant activity by means of scavenger activity towards 2,2-diphenyl-1-picrylhydrazyl (DPPH) and the Ferric Ion Reducing Power (FRAP) assay. Some compounds exhibited promising antioxidant properties.

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Iodine-mediated Unique Intramolecular Rearrangement of Amide to Nitrile in Thiophenes and their Antioxidant Potential Studies

Lett. Org. Chem. 22, 837 (2025); https://doi.org/10.2174/0115701786357751250507110749

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General experimental protocols, characterization details, ¹H-NMR, ¹³C-NMR, and HRMS spectra of compounds are in the supporting information file.

Article Type: Research Article

Keyword(s): Amide to nitrile; antioxidant studies; intramolecular rearrangement; iodine; thiophene; urea

Iodine-mediated Unique Intramolecular Rearrangement of Amide to Nitrile in Thiophenes and their Antioxidant Potential Studies

Abstract

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General experimental protocols, characterization details, ¹H-NMR, ¹³C-NMR, and HRMS spectra of compounds are in the supporting information file.

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Iodine-mediated Unique Intramolecular Rearrangement of Amide to Nitrile in Thiophenes and their Antioxidant Potential Studies

Abstract

General experimental protocols, characterization details, 1H-NMR, 13C-NMR, and HRMS spectra of compounds are in the supporting information file.

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General experimental protocols, characterization details, ¹H-NMR, ¹³C-NMR, and HRMS spectra of compounds are in the supporting information file.