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Metal-free synthesis of 1,N 6-ethenoadenines from N 6-propargyl-adenines via NIS mediated radical cascade reaction. 2019
Ruchun Yang, and
Si Deng, and
Xiang-You Dong, and
Xianrong Song, and
Hu Cai, and
Jiang Bai, and
Qiang Xiao
Institute of Chemistry, Nanchang University Nanchang 330031 Jiangxi Province China caihu@ncu.edu.cn.
In the present paper, an efficient approach for the construction of 1,N 6-ethenoadenines from conveniently prepared N 6-propargyl-adenines is developed. This reaction merges N-iodosuccinimide radical initiation and aerobic aminooxygenation in dioxane. This mild, 5-exo-dig, and metal-free cascade reaction could be applied to a wide substrate scope to provide 1,N 6-ethenoadenines in moderate to good yields. The reaction mechanism was proposed and tested using radical inhibitor (butylated hydroxytoluene) and isotopic labelling (18O2) experiments.
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