Switchable synthesis of benzimidazole/quinoxaline C -glycosides with o -phenylenediamines and sulfoxonium ylide glyco-reagents
A novel switchable approach for the synthesis of benzimidazole/quinoxaline C -glycosides is introduced. This versatile catalytic system facilitates the reaction of o -phenylenediamines with carbonyl sulfoxonium ylide glyco-reagents under mild conditions to selectively form 2-glycoside quinoxalines a...
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| Published in | Chemical communications (Cambridge, England) Vol. 61; no. 65; pp. 12131 - 12134 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
07.08.2025
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| Subjects | |
| Online Access | Get full text |
| ISSN | 1359-7345 1364-548X 1364-548X |
| DOI | 10.1039/D5CC02719E |
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| Abstract | A novel switchable approach for the synthesis of benzimidazole/quinoxaline C -glycosides is introduced. This versatile catalytic system facilitates the reaction of o -phenylenediamines with carbonyl sulfoxonium ylide glyco-reagents under mild conditions to selectively form 2-glycoside quinoxalines and 2-glycoside benzimidazoles, through [OsCl 2 ( p -cymene)] 2 and AgSbF 6 catalysts, respectively. The process is adaptable as it can generate a variety of heteroarene C -glycosides by accommodating a wide range of sugar donors. It is also ideal for the modification of compounds like varenicline due to its excellent functional group compatibility, mild reaction conditions, and wide substrate range. |
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| AbstractList | A novel switchable approach for the synthesis of benzimidazole/quinoxaline C-glycosides is introduced. This versatile catalytic system facilitates the reaction of o-phenylenediamines with carbonyl sulfoxonium ylide glyco-reagents under mild conditions to selectively form 2-glycoside quinoxalines and 2-glycoside benzimidazoles, through [OsCl2(p-cymene)]2 and AgSbF6 catalysts, respectively. The process is adaptable as it can generate a variety of heteroarene C-glycosides by accommodating a wide range of sugar donors. It is also ideal for the modification of compounds like varenicline due to its excellent functional group compatibility, mild reaction conditions, and wide substrate range.A novel switchable approach for the synthesis of benzimidazole/quinoxaline C-glycosides is introduced. This versatile catalytic system facilitates the reaction of o-phenylenediamines with carbonyl sulfoxonium ylide glyco-reagents under mild conditions to selectively form 2-glycoside quinoxalines and 2-glycoside benzimidazoles, through [OsCl2(p-cymene)]2 and AgSbF6 catalysts, respectively. The process is adaptable as it can generate a variety of heteroarene C-glycosides by accommodating a wide range of sugar donors. It is also ideal for the modification of compounds like varenicline due to its excellent functional group compatibility, mild reaction conditions, and wide substrate range. A novel switchable approach for the synthesis of benzimidazole/quinoxaline -glycosides is introduced. This versatile catalytic system facilitates the reaction of -phenylenediamines with carbonyl sulfoxonium ylide glyco-reagents under mild conditions to selectively form 2-glycoside quinoxalines and 2-glycoside benzimidazoles, through [OsCl ( -cymene)] and AgSbF catalysts, respectively. The process is adaptable as it can generate a variety of heteroarene -glycosides by accommodating a wide range of sugar donors. It is also ideal for the modification of compounds like varenicline due to its excellent functional group compatibility, mild reaction conditions, and wide substrate range. A novel switchable approach for the synthesis of benzimidazole/quinoxaline C -glycosides is introduced. This versatile catalytic system facilitates the reaction of o -phenylenediamines with carbonyl sulfoxonium ylide glyco-reagents under mild conditions to selectively form 2-glycoside quinoxalines and 2-glycoside benzimidazoles, through [OsCl 2 ( p -cymene)] 2 and AgSbF 6 catalysts, respectively. The process is adaptable as it can generate a variety of heteroarene C -glycosides by accommodating a wide range of sugar donors. It is also ideal for the modification of compounds like varenicline due to its excellent functional group compatibility, mild reaction conditions, and wide substrate range. A novel switchable approach for the synthesis of benzimidazole/quinoxaline C-glycosides is introduced. This versatile catalytic system facilitates the reaction of o-phenylenediamines with carbonyl sulfoxonium ylide glyco-reagents under mild conditions to selectively form 2-glycoside quinoxalines and 2-glycoside benzimidazoles, through [OsCl2(p-cymene)]2 and AgSbF6 catalysts, respectively. The process is adaptable as it can generate a variety of heteroarene C-glycosides by accommodating a wide range of sugar donors. It is also ideal for the modification of compounds like varenicline due to its excellent functional group compatibility, mild reaction conditions, and wide substrate range. |
| Author | Hu, Xin-Yue Wen, Miao-Miao Liu, Xu-Ge Ren, Xiao-Xi Liu, Deng-Yin Zhang, Cong-Zhen |
| Author_xml | – sequence: 1 givenname: Deng-Yin surname: Liu fullname: Liu, Deng-Yin organization: The Zhongzhou Laboratory for Integrative Biology, School of Pharmacy, Henan University, Kaifeng, Henan 475004, China – sequence: 2 givenname: Xin-Yue surname: Hu fullname: Hu, Xin-Yue organization: The Zhongzhou Laboratory for Integrative Biology, School of Pharmacy, Henan University, Kaifeng, Henan 475004, China – sequence: 3 givenname: Cong-Zhen surname: Zhang fullname: Zhang, Cong-Zhen organization: The Zhongzhou Laboratory for Integrative Biology, School of Pharmacy, Henan University, Kaifeng, Henan 475004, China – sequence: 4 givenname: Miao-Miao surname: Wen fullname: Wen, Miao-Miao organization: The Zhongzhou Laboratory for Integrative Biology, School of Pharmacy, Henan University, Kaifeng, Henan 475004, China – sequence: 5 givenname: Xiao-Xi surname: Ren fullname: Ren, Xiao-Xi organization: The Zhongzhou Laboratory for Integrative Biology, School of Pharmacy, Henan University, Kaifeng, Henan 475004, China – sequence: 6 givenname: Xu-Ge orcidid: 0000-0003-1878-2525 surname: Liu fullname: Liu, Xu-Ge organization: The Zhongzhou Laboratory for Integrative Biology, School of Pharmacy, Henan University, Kaifeng, Henan 475004, China |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/40662315$$D View this record in MEDLINE/PubMed |
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| Snippet | A novel switchable approach for the synthesis of benzimidazole/quinoxaline C -glycosides is introduced. This versatile catalytic system facilitates the... A novel switchable approach for the synthesis of benzimidazole/quinoxaline -glycosides is introduced. This versatile catalytic system facilitates the reaction... A novel switchable approach for the synthesis of benzimidazole/quinoxaline C-glycosides is introduced. This versatile catalytic system facilitates the reaction... |
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| SubjectTerms | Carbonyls Functional groups Glycosides Quinoxalines Reagents Synthesis |
| Title | Switchable synthesis of benzimidazole/quinoxaline C -glycosides with o -phenylenediamines and sulfoxonium ylide glyco-reagents |
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