Issue 2, 2010
From the journal:

Organic & Biomolecular Chemistry

Nucleoside and nucleotide analogues by catalyst free Huisgen nitrile oxide–alkyne1,3-dipolar cycloaddition†

Virginie Algay,a   Ishwar Singha  and  Frances Heaney*a  

* Corresponding authors

a Department of Chemistry, National University of Ireland, Maynooth, Co. Kildare, Republic of Ireland
E-mail: mary.f.heaney@nuim.ie
Fax: +353 1708 3815
Tel: +353 1708 3802

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.

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

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Article information

DOI
https://doi.org/10.1039/B917450H
Article type
Paper
Submitted
25 Aug 2009
Accepted
25 Sep 2009
First published
28 Oct 2009

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

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

V. Algay, I. Singh and F. Heaney, Org. Biomol. Chem., 2010, 8, 391 DOI: 10.1039/B917450H

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