Substituent-Controllable Cascade Regioselective Annulation of <i>β</i>-Enaminones with <i>N</i>-Sulfonyl Triazoles for Modular Access to Imidazoles and Pyrroles
A controllable synthesis of trisubstituted imidazoles and pyrroles has been developed through rhodium(II)-catalyzed regioselective annulation of <i>N</i>-sulfonyl-1,2,3-trizaoles with <i>β</i>-enaminones. The imidazole ring was formed through a 1,1-insertion of the N-H bond t...
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MDPI AG
2023-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/11/4416 |
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| author | Hua Wang Tongtong Zhou Mengdi Wu Qingqing Ye Xinwei He |
| author_facet | Hua Wang Tongtong Zhou Mengdi Wu Qingqing Ye Xinwei He |
| author_sort | Hua Wang |
| collection | DOAJ |
| description | A controllable synthesis of trisubstituted imidazoles and pyrroles has been developed through rhodium(II)-catalyzed regioselective annulation of <i>N</i>-sulfonyl-1,2,3-trizaoles with <i>β</i>-enaminones. The imidazole ring was formed through a 1,1-insertion of the N-H bond to α-imino rhodium carbene, followed by a subsequent intramolecular 1,4-conjugate addition. This occurred when the <i>α</i>-carbon atom of the amino group was bearing a methyl group. Additionally, the pyrrole ring was constructed by utilizing a phenyl substituent and undergoing intramolecular nucleophilic addition. The mild conditions, good tolerance towards functional groups, gram-scale synthesis capability, and ability to undergo valuable transformations of the products qualify this unique protocol as an efficient tool for the synthesis of <i>N</i>-heterocycles. |
| first_indexed | 2024-03-11T03:01:54Z |
| format | Article |
| id | doaj.art-a7a1b89a5b294ebeaa9b22e6cd40b26e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T03:01:54Z |
| publishDate | 2023-05-01 |
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| series | Molecules |
| spelling | doaj.art-a7a1b89a5b294ebeaa9b22e6cd40b26e2023-11-18T08:16:20ZengMDPI AGMolecules1420-30492023-05-012811441610.3390/molecules28114416Substituent-Controllable Cascade Regioselective Annulation of <i>β</i>-Enaminones with <i>N</i>-Sulfonyl Triazoles for Modular Access to Imidazoles and PyrrolesHua Wang0Tongtong Zhou1Mengdi Wu2Qingqing Ye3Xinwei He4Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, ChinaKey Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, ChinaKey Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, ChinaDepartment of Medicine, Chuzhou City Vocation College, Chuzhou 239000, ChinaKey Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, ChinaA controllable synthesis of trisubstituted imidazoles and pyrroles has been developed through rhodium(II)-catalyzed regioselective annulation of <i>N</i>-sulfonyl-1,2,3-trizaoles with <i>β</i>-enaminones. The imidazole ring was formed through a 1,1-insertion of the N-H bond to α-imino rhodium carbene, followed by a subsequent intramolecular 1,4-conjugate addition. This occurred when the <i>α</i>-carbon atom of the amino group was bearing a methyl group. Additionally, the pyrrole ring was constructed by utilizing a phenyl substituent and undergoing intramolecular nucleophilic addition. The mild conditions, good tolerance towards functional groups, gram-scale synthesis capability, and ability to undergo valuable transformations of the products qualify this unique protocol as an efficient tool for the synthesis of <i>N</i>-heterocycles.https://www.mdpi.com/1420-3049/28/11/4416annulation<i>β</i>-enaminonesimidazolespyrroles<i>N</i>-sulfonyl trizaoles |
| spellingShingle | Hua Wang Tongtong Zhou Mengdi Wu Qingqing Ye Xinwei He Substituent-Controllable Cascade Regioselective Annulation of <i>β</i>-Enaminones with <i>N</i>-Sulfonyl Triazoles for Modular Access to Imidazoles and Pyrroles Molecules annulation <i>β</i>-enaminones imidazoles pyrroles <i>N</i>-sulfonyl trizaoles |
| title | Substituent-Controllable Cascade Regioselective Annulation of <i>β</i>-Enaminones with <i>N</i>-Sulfonyl Triazoles for Modular Access to Imidazoles and Pyrroles |
| title_full | Substituent-Controllable Cascade Regioselective Annulation of <i>β</i>-Enaminones with <i>N</i>-Sulfonyl Triazoles for Modular Access to Imidazoles and Pyrroles |
| title_fullStr | Substituent-Controllable Cascade Regioselective Annulation of <i>β</i>-Enaminones with <i>N</i>-Sulfonyl Triazoles for Modular Access to Imidazoles and Pyrroles |
| title_full_unstemmed | Substituent-Controllable Cascade Regioselective Annulation of <i>β</i>-Enaminones with <i>N</i>-Sulfonyl Triazoles for Modular Access to Imidazoles and Pyrroles |
| title_short | Substituent-Controllable Cascade Regioselective Annulation of <i>β</i>-Enaminones with <i>N</i>-Sulfonyl Triazoles for Modular Access to Imidazoles and Pyrroles |
| title_sort | substituent controllable cascade regioselective annulation of i β i enaminones with i n i sulfonyl triazoles for modular access to imidazoles and pyrroles |
| topic | annulation <i>β</i>-enaminones imidazoles pyrroles <i>N</i>-sulfonyl trizaoles |
| url | https://www.mdpi.com/1420-3049/28/11/4416 |
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