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Synthesis 2008(21): 3453-3460  
DOI: 10.1055/s-0028-1083156
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel, Simple Cyclocondensation Reaction Towards Glycosyl Triazines

Vincent Kikelja,b, Karine Juliennea,b, Pascal Janviera,b, Jean-Claude Meslina,b, David Deniaud*a,b
a CEISAM, Chimie Et Interdisciplinarité, Synthèse, Analyse, Modélisation, UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France
b CNRS, UMR CNRS 6230, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France
Fax: +33(2)51125402; e-Mail: david.deniaud@univ-nantes.fr;
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Publikationsverlauf

Received 11 June 2008
Publikationsdatum:
25. September 2008 (online)

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Abstract

Sugars bearing an isothiocyanate moiety at C-1 react with diazadienium iodide to afford glycosyl triazines that represent, through an easy cyclocondensation reaction step, a flexible entry to different nucleoside analogues. We herein demonstrate that this [4+2] cycloaddition reaction occurs with total regiocontrol and good yields. Subsequent transformation of the thiocarbonyl into a carbonyl, and nucleophilic substitution of the methylsulfanyl group by ammonia, yields the 5-azacytidine analogues. All compounds were fully characterised by IR, HRMS, and ¹³C and ¹H NMR (COSY­, HMBC and HMQC).

Key words

nucleosides - triazines - cycloaddition - 5-azacytidine - heterochemistry

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