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.
Authors
- Patchanita Thamyongkit (ORCID: https://orcid.org/0000-0003-0261-3014)
- Sumrit Wacharasindhu (ORCID: https://orcid.org/0000-0001-6940-1329)
- Mongkol Sukwattanasinitt (ORCID: https://orcid.org/0000-0002-8315-9679)
- Preecha Phuwapraisirisan (ORCID: https://orcid.org/0000-0001-6481-7712)
- Khuyen Thu Nguyen (ORCID: https://orcid.org/0009-0009-6709-2791)
- Permsak Chairat
- Thao Nguyen Thanh Huynh (ORCID: https://orcid.org/0009-0003-4070-0124)
- Thanyaporn Kostphan
- Khoa Nguyen (ORCID: https://orcid.org/0009-0009-6026-444X)
Institutions
- Chulalongkorn University (TH)
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