A mild synthesis of <i>o</i>-ureidobenzonitrile derivatives <i>via</i> iodide-mediated electrolysis from 2-aminobenzamides

An efficient electrochemical synthesis of <i>o</i>-ureidobenzonitrile derivatives from 2-aminobenzamides and isothiocyanates was developed using ammonium iodide as the electrolyte and mediator (0.5 equivalent). This iodide-mediated desulfurization-cyclization process proceeds under mild conditions in an undivided cell with graphite electrodes, delivering a broad range of products in good to excellent yields (44 examples, up to 98%). This method avoids the use of stoichiometric amounts of strong oxidants and toxic solvents, offering a greener alternative to traditional approaches. The synthesized compounds were evaluated for α-glucosidase inhibition and antioxidant activity, demonstrating moderate biological efficacy and highlighting their potential for pharmaceutical applications.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob00971e
Citations
1
Primary Topic
Synthesis and Biological Evaluation
Type
article
Field-Weighted Citation Impact
0.94
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A mild synthesis of o-ureidobenzonitrile derivatives via iodide-mediated electrolysis from 2-aminobenzamides

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A mild synthesis of o-ureidobenzonitrile derivatives via iodide-mediated electrolysis from 2-aminobenzamides

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article en
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Abstract

An efficient electrochemical synthesis of <i>o</i>-ureidobenzonitrile derivatives from 2-aminobenzamides and isothiocyanates was developed using ammonium iodide as the electrolyte and mediator (0.5 equivalent). This iodide-mediated desulfurization-cyclization process proceeds under mild conditions in an undivided cell with graphite electrodes, delivering a broad range of products in good to excellent yields (44 examples, up to 98%). This method avoids the use of stoichiometric amounts of strong oxidants and toxic solvents, offering a greener alternative to traditional approaches. The synthesized compounds were evaluated for α-glucosidase inhibition and antioxidant activity, demonstrating moderate biological efficacy and highlighting their potential for pharmaceutical applications.

Organic & Biomolecular ChemistryVol. 23(33)
Chulalongkorn University (TH)
Openalex Percentile: Top 23%
Synthesis and Biological Evaluation
0.94
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