Metal-Free Synthesis of Benzimidazolinones via Oxidative Cyclization Under Hypervalent Iodine Catalysis
Benzimidazolinones exhibit unique biological activities and serve as building blocks in synthesizing pharmaceutical compounds. Although multiple synthetic approaches involving intermolecular cyclization reactions have been reported, intramolecular cyclization reactions are scarce, and more rational...
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| Language: | English |
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MDPI AG
2025-03-01
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| Series: | Chemistry |
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| Online Access: | https://www.mdpi.com/2624-8549/7/2/50 |
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| author | Mayu Hirashima Syotaro Hamatani Hirotaka Sasa Naoko Takenaga Tomonori Hanasaki Toshifumi Dohi |
| author_facet | Mayu Hirashima Syotaro Hamatani Hirotaka Sasa Naoko Takenaga Tomonori Hanasaki Toshifumi Dohi |
| author_sort | Mayu Hirashima |
| collection | DOAJ |
| description | Benzimidazolinones exhibit unique biological activities and serve as building blocks in synthesizing pharmaceutical compounds. Although multiple synthetic approaches involving intermolecular cyclization reactions have been reported, intramolecular cyclization reactions are scarce, and more rational synthetic methods are required. Hypervalent iodine-catalyzed oxidative C–N coupling is a potentially effective approach for synthesizing benzimidazolinones under metal-free conditions. In this study, we present a method utilizing hypervalent iodine catalysis for the oxidative cyclization of <i>N’</i>-aryl urea compounds, resulting in the first metal-free synthesis of various benzimidazolinones. |
| format | Article |
| id | doaj-art-ad1ad8d4511341fc98a37f4cb5bf6973 |
| institution | OA Journals |
| issn | 2624-8549 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemistry |
| spelling | doaj-art-ad1ad8d4511341fc98a37f4cb5bf69732025-08-20T02:17:14ZengMDPI AGChemistry2624-85492025-03-01725010.3390/chemistry7020050Metal-Free Synthesis of Benzimidazolinones via Oxidative Cyclization Under Hypervalent Iodine CatalysisMayu Hirashima0Syotaro Hamatani1Hirotaka Sasa2Naoko Takenaga3Tomonori Hanasaki4Toshifumi Dohi5Graduate School of Life Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu 525-8577, Shiga, JapanGraduate School of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu 525-8577, Shiga, JapanSchool of Pharmacy and Pharmaceutical Sciences, Mukogawa Women’s University, 11-68 Koshien Kyu-ban-cho, Nishinomiya 663-8179, Hyogo, JapanFaculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku-ku, Nagoya 468-8503, Aichi, JapanGraduate School of Life Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu 525-8577, Shiga, JapanGraduate School of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu 525-8577, Shiga, JapanBenzimidazolinones exhibit unique biological activities and serve as building blocks in synthesizing pharmaceutical compounds. Although multiple synthetic approaches involving intermolecular cyclization reactions have been reported, intramolecular cyclization reactions are scarce, and more rational synthetic methods are required. Hypervalent iodine-catalyzed oxidative C–N coupling is a potentially effective approach for synthesizing benzimidazolinones under metal-free conditions. In this study, we present a method utilizing hypervalent iodine catalysis for the oxidative cyclization of <i>N’</i>-aryl urea compounds, resulting in the first metal-free synthesis of various benzimidazolinones.https://www.mdpi.com/2624-8549/7/2/50hypervalent iodine catalysisoxidative cyclizationelectrophilic aminationbenzimidazolinone<i>N</i>-methoxy-<i>N</i>′-phenylurea |
| spellingShingle | Mayu Hirashima Syotaro Hamatani Hirotaka Sasa Naoko Takenaga Tomonori Hanasaki Toshifumi Dohi Metal-Free Synthesis of Benzimidazolinones via Oxidative Cyclization Under Hypervalent Iodine Catalysis Chemistry hypervalent iodine catalysis oxidative cyclization electrophilic amination benzimidazolinone <i>N</i>-methoxy-<i>N</i>′-phenylurea |
| title | Metal-Free Synthesis of Benzimidazolinones via Oxidative Cyclization Under Hypervalent Iodine Catalysis |
| title_full | Metal-Free Synthesis of Benzimidazolinones via Oxidative Cyclization Under Hypervalent Iodine Catalysis |
| title_fullStr | Metal-Free Synthesis of Benzimidazolinones via Oxidative Cyclization Under Hypervalent Iodine Catalysis |
| title_full_unstemmed | Metal-Free Synthesis of Benzimidazolinones via Oxidative Cyclization Under Hypervalent Iodine Catalysis |
| title_short | Metal-Free Synthesis of Benzimidazolinones via Oxidative Cyclization Under Hypervalent Iodine Catalysis |
| title_sort | metal free synthesis of benzimidazolinones via oxidative cyclization under hypervalent iodine catalysis |
| topic | hypervalent iodine catalysis oxidative cyclization electrophilic amination benzimidazolinone <i>N</i>-methoxy-<i>N</i>′-phenylurea |
| url | https://www.mdpi.com/2624-8549/7/2/50 |
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