A mild and scalable one-pot synthesis of N-substituted 2-aminobenzimidazoles via visible light mediated cyclodesulfurization
Abstract A visible light mediated photocatalyst-free synthesis of N-substituted 2-aminobenzimidazoles directly from o-phenylenediamines and isothiocyanates is developed in a one-pot fashion. This one-pot reaction proceeds through three steps: N-substitution of o-phenylenediamines, thiourea formation...
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Nature Portfolio
2025-02-01
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| Series: | Scientific Reports |
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| Online Access: | https://doi.org/10.1038/s41598-025-86772-8 |
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| author | Tanawat Rerkrachaneekorn Rose Malina Annuur Soraya Pornsuwan Mongkol Sukwattanasinitt Sumrit Wacharasindhu |
| author_facet | Tanawat Rerkrachaneekorn Rose Malina Annuur Soraya Pornsuwan Mongkol Sukwattanasinitt Sumrit Wacharasindhu |
| author_sort | Tanawat Rerkrachaneekorn |
| collection | DOAJ |
| description | Abstract A visible light mediated photocatalyst-free synthesis of N-substituted 2-aminobenzimidazoles directly from o-phenylenediamines and isothiocyanates is developed in a one-pot fashion. This one-pot reaction proceeds through three steps: N-substitution of o-phenylenediamines, thiourea formation and visible light mediated cyclodesulfurization. This method enables the rapid and efficient synthesis of structurally diverse N-substituted 2-aminobenzimidazoles, achieving yields up to 92% across 69 examples. The practicality of the reaction is demonstrated by gram-scale synthesis. The key advantages of this method include the use of less toxic solvent in aqueous media, the elimination of photocatalyst, and a simple, practical setup (one-pot, open-flask, and ambient temperature). Mechanistic insights are gathered through control experiments, including light on/off cycles and radical inhibition studies. The results indicate that the reaction involves with radical pathway mediated by visible light. |
| format | Article |
| id | doaj-art-06f2fb00283d4c6b8b5de749b45356e8 |
| institution | Kabale University |
| issn | 2045-2322 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj-art-06f2fb00283d4c6b8b5de749b45356e82025-02-09T12:33:28ZengNature PortfolioScientific Reports2045-23222025-02-0115111810.1038/s41598-025-86772-8A mild and scalable one-pot synthesis of N-substituted 2-aminobenzimidazoles via visible light mediated cyclodesulfurizationTanawat Rerkrachaneekorn0Rose Malina Annuur1Soraya Pornsuwan2Mongkol Sukwattanasinitt3Sumrit Wacharasindhu4Nanotec-CU Center of Excellence on Food and Agriculture, Department of Chemistry, Faculty of Science, Chulalongkorn UniversityNanotec-CU Center of Excellence on Food and Agriculture, Department of Chemistry, Faculty of Science, Chulalongkorn UniversityDepartment of Chemistry, Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol UniversityNanotec-CU Center of Excellence on Food and Agriculture, Department of Chemistry, Faculty of Science, Chulalongkorn UniversityNanotec-CU Center of Excellence on Food and Agriculture, Department of Chemistry, Faculty of Science, Chulalongkorn UniversityAbstract A visible light mediated photocatalyst-free synthesis of N-substituted 2-aminobenzimidazoles directly from o-phenylenediamines and isothiocyanates is developed in a one-pot fashion. This one-pot reaction proceeds through three steps: N-substitution of o-phenylenediamines, thiourea formation and visible light mediated cyclodesulfurization. This method enables the rapid and efficient synthesis of structurally diverse N-substituted 2-aminobenzimidazoles, achieving yields up to 92% across 69 examples. The practicality of the reaction is demonstrated by gram-scale synthesis. The key advantages of this method include the use of less toxic solvent in aqueous media, the elimination of photocatalyst, and a simple, practical setup (one-pot, open-flask, and ambient temperature). Mechanistic insights are gathered through control experiments, including light on/off cycles and radical inhibition studies. The results indicate that the reaction involves with radical pathway mediated by visible light.https://doi.org/10.1038/s41598-025-86772-8Visible light mediatedN-substituted 2-aminobenzimidazolesPhotocatalyst-freeThioureaCyclodesulfurization |
| spellingShingle | Tanawat Rerkrachaneekorn Rose Malina Annuur Soraya Pornsuwan Mongkol Sukwattanasinitt Sumrit Wacharasindhu A mild and scalable one-pot synthesis of N-substituted 2-aminobenzimidazoles via visible light mediated cyclodesulfurization Scientific Reports Visible light mediated N-substituted 2-aminobenzimidazoles Photocatalyst-free Thiourea Cyclodesulfurization |
| title | A mild and scalable one-pot synthesis of N-substituted 2-aminobenzimidazoles via visible light mediated cyclodesulfurization |
| title_full | A mild and scalable one-pot synthesis of N-substituted 2-aminobenzimidazoles via visible light mediated cyclodesulfurization |
| title_fullStr | A mild and scalable one-pot synthesis of N-substituted 2-aminobenzimidazoles via visible light mediated cyclodesulfurization |
| title_full_unstemmed | A mild and scalable one-pot synthesis of N-substituted 2-aminobenzimidazoles via visible light mediated cyclodesulfurization |
| title_short | A mild and scalable one-pot synthesis of N-substituted 2-aminobenzimidazoles via visible light mediated cyclodesulfurization |
| title_sort | mild and scalable one pot synthesis of n substituted 2 aminobenzimidazoles via visible light mediated cyclodesulfurization |
| topic | Visible light mediated N-substituted 2-aminobenzimidazoles Photocatalyst-free Thiourea Cyclodesulfurization |
| url | https://doi.org/10.1038/s41598-025-86772-8 |
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