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Synthesis 2010(16): 2811-2815  
DOI: 10.1055/s-0029-1218839
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Concerning the Nucleophilic Displacement of a Methylsulfanyl Group on Substituted Pyrimidinones

Vincent Kikelj, Sylvain Grosjean, Jean-Claude Meslin, Karine Julienne, David Deniaud*
Université de Nantes, CEISAM, Chimie Et Interdisciplinarité, Synthèse, Analyse, Modélisation, UMR CNRS 6230, UFR des Sciences et des Techniques, 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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Publication History

Received 13 April 2010
Publication Date:
25 June 2010 (online)

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Abstract

The nucleophilic displacement of a methylsulfanyl group (SMe) at the C2-position on a pyrimidin-4-one scaffold was achieved after oxidation into a methylsulfonyl group (SO2Me) using dimethyldioxirane (DMDO), a powerful electrophilic oxygen atom transfer agent. The introduction of amino groups as well as formation of carbon-carbon bonds was thus demonstrated.

Key words

dimethyldioxirane - oxidation - nucleophilic substitutions - heterocycles - DMDO