Synthesis of cycloalkyl substituted purine nucleosides via a metal-free radical route. Issue 18 (21st April 2016)

• Record Type: Journal Article
• Authors: Wang, Dong-Chao; Xia, Ran; Xie, Ming-Sheng; Qu, Gui-Rong; Guo, Hai-Ming
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 18(2016)
• Page Start: 4189
• Page End: 4193
• Publication Date: 2016-04-21
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob00596a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : 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. Abstract : An efficient route to synthesize cycloalkyl substituted purine nucleosides was developed. This metal-free C–H activation was accomplished by a t BuOO t Bu initiated radical reaction. By adjusting the amount of t BuOO t Bu 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.