Synthesis of cycloalkyl substituted purine nucleosides via a metal-free radical route.
An efficient route to synthesize cycloalkyl substituted purine nucleosides was developed. This metal-free C-H activation was accomplished by a tBuOOtBu initiated radical reaction. By adjusting the amount of tBuOOtBu and reaction time, the selective synthesis of C6-monocycloalkyl or C6,C8-dicycloalkyl substituted purine nucleosides could be realized. Furthermore, uracil and related nucleosides were also suitable substrates, giving the C5-cyclohexyl substituted uracil derivatives in good yields with excellent regioselectivities.
School of Environment, Henan Normal University, Xinxiang, Henan province 453007, P. R. China and School of Chemistry and Chemical Engineering, Key Laboratory of Green Chemical Media and Reactions of Ministry of Education, Henan Normal University, 46 Jianshe Road, Xinxiang, 453007, P. R. China. quguir@sina.com ghm@htu.edu.cn.
Dong-Chao
DC
Wang
School of Environment, Henan Normal University, Xinxiang, Henan province 453007, P. R. China and School of Chemistry and Chemical Engineering, Xinxiang University, Xinxiang 453003, China.
Ran
R
Xia
School of Chemistry and Chemical Engineering, Key Laboratory of Green Chemical Media and Reactions of Ministry of Education, Henan Normal University, 46 Jianshe Road, Xinxiang, 453007, P. R. China. quguir@sina.com ghm@htu.edu.cn.
Ming-Sheng
MS
Xie
School of Chemistry and Chemical Engineering, Key Laboratory of Green Chemical Media and Reactions of Ministry of Education, Henan Normal University, 46 Jianshe Road, Xinxiang, 453007, P. R. China. quguir@sina.com ghm@htu.edu.cn.
Gui-Rong
GR
Qu
School of Environment, Henan Normal University, Xinxiang, Henan province 453007, P. R. China and School of Chemistry and Chemical Engineering, Key Laboratory of Green Chemical Media and Reactions of Ministry of Education, Henan Normal University, 46 Jianshe Road, Xinxiang, 453007, P. R. China. quguir@sina.com ghm@htu.edu.cn.
Hai-Ming
HM
Guo
D000473:Alkanes / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D005609:Free Radicals / Q000737:chemistry; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*
D000473:Alkanes; D005609:Free Radicals; D011684:Purine Nucleosides