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通过NIS介导的自由基串联反应由炔丙基腺嘌呤无金属合成1, -乙烯基腺嘌呤。

Metal-free synthesis of 1, -ethenoadenines from -propargyl-adenines NIS mediated radical cascade reaction.

作者信息

Yang Ruchun, Deng Si, Dong Xiang-You, Song Xianrong, Cai Hu, Bai Jiang, Xiao Qiang

机构信息

Institute of Chemistry, Nanchang University Nanchang 330031 Jiangxi Province China

Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Key Laboratory of Organic Chemistry Nanchang 330013 Jiangxi Province China

出版信息

RSC Adv. 2019 Nov 26;9(66):38897-38901. doi: 10.1039/c9ra09198j. eCollection 2019 Nov 25.

DOI:10.1039/c9ra09198j
PMID:35540232
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9075968/
Abstract

In the present paper, an efficient approach for the construction of 1, -ethenoadenines from conveniently prepared -propargyl-adenines is developed. This reaction merges -iodosuccinimide radical initiation and aerobic aminooxygenation in dioxane. This mild, , and metal-free cascade reaction could be applied to a wide substrate scope to provide 1, -ethenoadenines in moderate to good yields. The reaction mechanism was proposed and tested using radical inhibitor (butylated hydroxytoluene) and isotopic labelling (O) experiments.

摘要

在本文中,开发了一种从方便制备的炔丙基腺嘌呤构建1, - 乙烯基腺嘌呤的有效方法。该反应在二氧六环中合并了碘代琥珀酰亚胺自由基引发和有氧氨氧化反应。这种温和、无金属的串联反应可应用于广泛的底物范围,以中等至良好的产率提供1, - 乙烯基腺嘌呤。使用自由基抑制剂(丁基化羟基甲苯)和同位素标记(O)实验对反应机理进行了推测和验证。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0534/9075968/750292e1b8f9/c9ra09198j-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0534/9075968/12557b32a356/c9ra09198j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0534/9075968/fa1b4bc48755/c9ra09198j-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0534/9075968/df664edda0f5/c9ra09198j-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0534/9075968/3b1c1512a5a8/c9ra09198j-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0534/9075968/750292e1b8f9/c9ra09198j-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0534/9075968/12557b32a356/c9ra09198j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0534/9075968/fa1b4bc48755/c9ra09198j-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0534/9075968/df664edda0f5/c9ra09198j-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0534/9075968/3b1c1512a5a8/c9ra09198j-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0534/9075968/750292e1b8f9/c9ra09198j-s3.jpg

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