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 inChemical communications (Cambridge, England) Vol. 61; no. 65; pp. 12131 - 12134
Main Authors Liu, Deng-Yin, Hu, Xin-Yue, Zhang, Cong-Zhen, Wen, Miao-Miao, Ren, Xiao-Xi, Liu, Xu-Ge
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 07.08.2025
Subjects
Carbonyls
Functional groups
Glycosides
Quinoxalines
Reagents
Synthesis
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ISSN1359-7345
1364-548X
1364-548X
DOI10.1039/D5CC02719E

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Summary: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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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/D5CC02719E