title: Nucleoside and nucleotide analogues by catalyst free Huisgen nitrile oxide-alkyne 1,3-dipolar cycloaddition.
abstract: 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.
authors.affiliation: Department of Chemistry, National University of Ireland, Maynooth, Co. Kildare, Republic of Ireland.
authors.forename: Virginie
authors.initials: V
authors.lastname: Algay
authors.forename: Ishwar
authors.initials: I
authors.lastname: Singh
authors.forename: Frances
authors.initials: F
authors.lastname: Heaney
mesh_terms: 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
chemical_list: D000480:Alkynes; D002241:Carbohydrates; D007555:Isoxazoles; D009570:Nitriles; D009705:Nucleosides; D009711:Nucleotides; D010087:Oxides; D012996:Solutions