Electrocatalytic oxidative C-H cycloamination towards tricyclic [1,2,4]triazolo-[3,4-i]purine nucleosides mediated by bromide ions

An environmentally benign electrochemical approach is presented to access a diversely functionalized [1,2,4]triazolo[3,4-i]purine heterocyclic framework. A bromide-mediated indirect oxidation strategy was utilized to promote intramolecular C(sp(2))-H cycloamination with high efficiency and under mil...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 10; no. 21; pp. 5369 - 5374
Main Authors Yang, Qi-Liang, Li, Wan-Wan, Zhang, Zhong-Xu, Zhang, Han-Meng, Li, Xian-Jia, Guo, Hai-Ming
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 24.10.2023
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Electrochemistry
Nucleosides
Organic chemistry
Oxidants
Oxidation
Oxidizing agents
Physical Sciences
Science & Technology
Substrates
XANTHINE-OXIDASE INHIBITOR
GENERAL SYNTHESES
AMINATION
ANNULATION
CHEMISTRY
HALOGEN
ELECTROCHEMICAL SYNTHESIS
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Summary:An environmentally benign electrochemical approach is presented to access a diversely functionalized [1,2,4]triazolo[3,4-i]purine heterocyclic framework. A bromide-mediated indirect oxidation strategy was utilized to promote intramolecular C(sp(2))-H cycloamination with high efficiency and under mild metal- and oxidant-free conditions. The method exhibits a broad substrate scope, which is well manifested by nucleoside substrates with one or even three hydroxy groups. A radical mechanism was proposed based on cyclic voltammetry and control experiments.
Bibliography:ObjectType-Article-1
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content type line 14
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d3qo01050c