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Visible‐Light‐Induced C2 Alkylation of Heterocyclic N‐Oxides with N‐Hydroxyphthalimide Esters under Metal‐Free Conditions
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2020-07-30 , DOI: 10.1002/adsc.202000517
Pi‐Tao Qin 1 , Jing Sun 1 , Fei Wang 1 , Jing‐Yun Wang 1 , He Wang 1 , Ming‐Dong Zhou 1
Affiliation  

A visible‐light‐induced site selective C−H alkylation of heterocyclic N‐oxides with N‐hydroxyphthalimide esters was developed using Eosin Y as the photocatalyst in the presence of Cs2CO3 under redox‐neutral and mild conditions. Using N‐hydroxyphthalimide esters as the radical precursors, quinoline and pyridine N‐oxides were readily coupled with a wide range of primary, secondary, and tertiary radicals to afford the desired alkylated heterocyclic N‐oxides in moderated to excellent yields. Importantly, this reaction protocol also successfully demonstrated its applications for the construction of glycosyl or bioactive natural dehydroabietic acid containing heterocyclic N‐oxides, as well as the pharmaceutical and agrochemical active alkylated quinine‐based functional molecules (potential antimalarial drug).

中文翻译:

在无金属条件下用N-羟基邻苯二甲酰亚胺酯在可见光下诱导杂环N-氧化物的C2烷基化

使用曙红Y作为光催化剂,在Cs 2 CO 3存在下,开发了可见光诱导的杂环N-氧化物与N-羟基邻苯二甲酰亚胺酯的CH选择性烷基化烷基化反应在氧化还原中性和温和条件下。使用N-羟基邻苯二甲酰亚胺酯作为自由基前体,喹啉和吡啶N-氧化物易于与各种伯,仲和叔基团偶联,以中等至极好的收率提供所需的烷基化杂环N-氧化物。重要的是,该反应方案还成功证明了其在糖基或生物活性天然脱氢松香酸含杂环N-氧化物以及药物和农用化学活性烷基化奎宁基功能分子(潜在的抗疟药)的构建中的应用。
更新日期:2020-07-30
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