Nucleoside and nucleotide analogues by catalyst free Huisgen nitrile oxide-alkyne 1,3-dipolar cycloaddition.
An efficient, catalyst free, 1,3-dipolar cycloaddition strategy to conjugate nucleosides and nucleotides with isoxazoles under atmospheric conditions and in an aqueous environment is reported. The protocol involves chloramine-T as a practical reagent to induce in situ nitrile oxide formation and the alkyne partner is attached to the sugar residue or the nucleobase. The reactions are regiospecific, fast and high yielding.
Algay
Virginie
V
Department of Chemistry, National University of Ireland, Maynooth, Co. Kildare, Republic of Ireland.
Singh
Ishwar
I
Heaney
Frances
F
D000480:Alkynes / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry; D002384:Catalysis; D007555:Isoxazoles / Q000138:chemical synthesis / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry*; D009705:Nucleosides / Q000737:chemistry*; D009711:Nucleotides / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D012996:Solutions
D000480:Alkynes; D002241:Carbohydrates; D007555:Isoxazoles; D009570:Nitriles; D009705:Nucleosides; D009711:Nucleotides; D010087:Oxides; D012996:Solutions