Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction.
Novel bitriazolyl nucleosides were synthesized via the Huisgen reaction, starting with 3-azidotriazole nucleoside (1). Surprisingly, its isomer, 5-azidotriazole nucleoside (1') did not yield the corresponding Huisgen reaction products efficiently because it was rapidly reduced to amine in the presence of Cu(II)-ascorbate. The significant differences between the reactivity of these two isomers in Cu(II)-ascorbate mediated reactions are mainly due to differences in their electronic properties and steric congestion as a result of different relative positions of the azido and the ribosyl moieties.
Xia
Yi
Y
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. China.
Li
Wei
W
Qu
Fanqi
F
Fan
Zhijin
Z
Liu
Xiufeng
X
Berro
Charles
C
Rauzy
Evelyne
E
Peng
Ling
L
D001205:Ascorbic Acid / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D007536:Isomerism; D008826:Microbial Sensitivity Tests; D008956:Models, Chemical; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D001386:Azides; D009705:Nucleosides; D014230:Triazoles; D003300:Copper; D001205:Ascorbic Acid