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Paper
Org. Biomol. Chem., 2010, 8, 391 - 397, DOI: 10.1039/b917450h
Nucleoside and nucleotide analogues by catalyst free Huisgen nitrile oxide–alkyne 1,3-dipolar cycloaddition
Virginie Algay, Ishwar Singh and Frances Heaney
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.
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