5-Aminopyrazole Dimerization: Cu-Promoted Switchable Synthesis of Pyrazole-Fused Pyridazines and Pyrazines via Direct Coupling of C-H/N-H, C-H/C-H, and N-H/N-H Bonds
A Cu-promoted highly chemoselective dimerization of 5-aminopyrazoles to produce pyrazole-fused pyridazines and pyrazines is reported. The protocol generates switchable products via the direct coupling of C-H/N-H, C-H/C-H and N-H/N-H bonds, with the merits of broad substrate scope and high functional...
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| Format: | Article |
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MDPI AG
2025-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/2/381 |
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| author | Yi-Xin Chai Jun-Jie Ren Yi-Ming Li Yi-Cheng Bai Qing-Qing Zhang Yi-Zhen Zhao Xue Yang Xiao-Han Zhang Xin-Shuang Zhang An-Xin Wu Yan-Ping Zhu Yuan-Yuan Sun |
| author_facet | Yi-Xin Chai Jun-Jie Ren Yi-Ming Li Yi-Cheng Bai Qing-Qing Zhang Yi-Zhen Zhao Xue Yang Xiao-Han Zhang Xin-Shuang Zhang An-Xin Wu Yan-Ping Zhu Yuan-Yuan Sun |
| author_sort | Yi-Xin Chai |
| collection | DOAJ |
| description | A Cu-promoted highly chemoselective dimerization of 5-aminopyrazoles to produce pyrazole-fused pyridazines and pyrazines is reported. The protocol generates switchable products via the direct coupling of C-H/N-H, C-H/C-H and N-H/N-H bonds, with the merits of broad substrate scope and high functional group compatibility. Gram-scale experiments demonstrated the potential applications of this reaction. Moreover, the preliminary fluorescence results uncovered that dipyrazole-fused pyridazines and pyrazines may have some potential applications in materials chemistry. |
| format | Article |
| id | doaj-art-b3b66dfcdc5b46669ea71ae115a5c2bf |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-b3b66dfcdc5b46669ea71ae115a5c2bf2025-01-24T13:43:50ZengMDPI AGMolecules1420-30492025-01-0130238110.3390/molecules300203815-Aminopyrazole Dimerization: Cu-Promoted Switchable Synthesis of Pyrazole-Fused Pyridazines and Pyrazines via Direct Coupling of C-H/N-H, C-H/C-H, and N-H/N-H BondsYi-Xin Chai0Jun-Jie Ren1Yi-Ming Li2Yi-Cheng Bai3Qing-Qing Zhang4Yi-Zhen Zhao5Xue Yang6Xiao-Han Zhang7Xin-Shuang Zhang8An-Xin Wu9Yan-Ping Zhu10Yuan-Yuan Sun11Key Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, School of Pharmacy, Yantai University, Yantai 264005, ChinaKey Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, School of Pharmacy, Yantai University, Yantai 264005, ChinaKey Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, School of Pharmacy, Yantai University, Yantai 264005, ChinaKey Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, School of Pharmacy, Yantai University, Yantai 264005, ChinaKey Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, School of Pharmacy, Yantai University, Yantai 264005, ChinaKey Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, School of Pharmacy, Yantai University, Yantai 264005, ChinaKey Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, School of Pharmacy, Yantai University, Yantai 264005, ChinaKey Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, School of Pharmacy, Yantai University, Yantai 264005, ChinaKey Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, School of Pharmacy, Yantai University, Yantai 264005, ChinaNational Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent Biosensor Technology and Health, College of Chemistry, Central China Normal University, Wuhan 430079, ChinaKey Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, School of Pharmacy, Yantai University, Yantai 264005, ChinaKey Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, School of Pharmacy, Yantai University, Yantai 264005, ChinaA Cu-promoted highly chemoselective dimerization of 5-aminopyrazoles to produce pyrazole-fused pyridazines and pyrazines is reported. The protocol generates switchable products via the direct coupling of C-H/N-H, C-H/C-H and N-H/N-H bonds, with the merits of broad substrate scope and high functional group compatibility. Gram-scale experiments demonstrated the potential applications of this reaction. Moreover, the preliminary fluorescence results uncovered that dipyrazole-fused pyridazines and pyrazines may have some potential applications in materials chemistry.https://www.mdpi.com/1420-3049/30/2/381Cu-promoted chemoselective dimerizationC-H/N-H, C-H/C-H, and N-H/N-H direct couplingswitchable productsfused pyridazines and pyrazines |
| spellingShingle | Yi-Xin Chai Jun-Jie Ren Yi-Ming Li Yi-Cheng Bai Qing-Qing Zhang Yi-Zhen Zhao Xue Yang Xiao-Han Zhang Xin-Shuang Zhang An-Xin Wu Yan-Ping Zhu Yuan-Yuan Sun 5-Aminopyrazole Dimerization: Cu-Promoted Switchable Synthesis of Pyrazole-Fused Pyridazines and Pyrazines via Direct Coupling of C-H/N-H, C-H/C-H, and N-H/N-H Bonds Molecules Cu-promoted chemoselective dimerization C-H/N-H, C-H/C-H, and N-H/N-H direct coupling switchable products fused pyridazines and pyrazines |
| title | 5-Aminopyrazole Dimerization: Cu-Promoted Switchable Synthesis of Pyrazole-Fused Pyridazines and Pyrazines via Direct Coupling of C-H/N-H, C-H/C-H, and N-H/N-H Bonds |
| title_full | 5-Aminopyrazole Dimerization: Cu-Promoted Switchable Synthesis of Pyrazole-Fused Pyridazines and Pyrazines via Direct Coupling of C-H/N-H, C-H/C-H, and N-H/N-H Bonds |
| title_fullStr | 5-Aminopyrazole Dimerization: Cu-Promoted Switchable Synthesis of Pyrazole-Fused Pyridazines and Pyrazines via Direct Coupling of C-H/N-H, C-H/C-H, and N-H/N-H Bonds |
| title_full_unstemmed | 5-Aminopyrazole Dimerization: Cu-Promoted Switchable Synthesis of Pyrazole-Fused Pyridazines and Pyrazines via Direct Coupling of C-H/N-H, C-H/C-H, and N-H/N-H Bonds |
| title_short | 5-Aminopyrazole Dimerization: Cu-Promoted Switchable Synthesis of Pyrazole-Fused Pyridazines and Pyrazines via Direct Coupling of C-H/N-H, C-H/C-H, and N-H/N-H Bonds |
| title_sort | 5 aminopyrazole dimerization cu promoted switchable synthesis of pyrazole fused pyridazines and pyrazines via direct coupling of c h n h c h c h and n h n h bonds |
| topic | Cu-promoted chemoselective dimerization C-H/N-H, C-H/C-H, and N-H/N-H direct coupling switchable products fused pyridazines and pyrazines |
| url | https://www.mdpi.com/1420-3049/30/2/381 |
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