Electrochemically driven reductive cyclization of o-nitroanilines: synthesis of 1,2-fused benzimidazoles and benzo[d]imidazoles
3
Issued Date
2025-01-01
Resource Type
ISSN
14770520
Scopus ID
2-s2.0-105002741779
Journal Title
Organic and Biomolecular Chemistry
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SCOPUS
Bibliographic Citation
Organic and Biomolecular Chemistry (2025)
Suggested Citation
Saetan J., Purahong N., La-Ongthong K., Hassa N., Chotsaeng N., Kuhakarn C., Meesin J. Electrochemically driven reductive cyclization of o-nitroanilines: synthesis of 1,2-fused benzimidazoles and benzo[d]imidazoles. Organic and Biomolecular Chemistry (2025). doi:10.1039/d5ob00214a Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/109757
Title
Electrochemically driven reductive cyclization of o-nitroanilines: synthesis of 1,2-fused benzimidazoles and benzo[d]imidazoles
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Abstract
The electrochemical synthesis of 1,2-fused benzimidazoles and benzo[d]imidazoles from o-nitroanilines in an undivided cell under constant current conditions was developed. The electrosynthesis proceeded through a tandem process involving nitro reduction/C(sp3)-H amination/condensation. The method can accommodate a broad range of o-nitroanilines and results in the desired products in yields of up to 99%. A plausible reaction mechanism was proposed on the basis of controlled experiments and cyclic voltammetry (CV) analysis. The benefits of the developed method include one-pot synthesis, open-air conditions, gram-scale synthesis and no requirement for a strong reductant.