Nucleoside and nucleotide analogues by catalyst free Huisgen nitrile oxide–alkyne 1,3-dipolar cycloaddition

Virginie Algay; Ishwar Singh; Frances Heaney

doi:10.1039/B917450H

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Organic & Biomolecular Chemistry

Issue 2, 2010

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Nucleoside and nucleotide analogues by catalyst free Huisgen nitrile oxide–alkyne 1,3-dipolar cycloaddition

Virginie Algay , Ishwar Singh and Frances Heaney

Org. Biomol. Chem., 2010, 8, 391-397

DOI: 10.1039/B917450H
Received 25 Aug 2009, Accepted 25 Sep 2009
First published on the web 28 Oct 2009

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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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NMR spectra of compounds 4–16 and 20–22
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Organic & Biomolecular Chemistry

Nucleoside and nucleotide analogues by catalyst free Huisgen nitrile oxide–alkyne 1,3-dipolar cycloaddition

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