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Synthesis 2007(14): 2193-2197  
DOI: 10.1055/s-2007-983748
PAPER
© Georg Thieme Verlag Stuttgart · New York

The Reactivity of Related 6-Amino- and 5,6-Diaminouracils Derived from 2-Amino-5-(phenoxymethyl)-2-oxazoline: Efficient Access to Bicyclic Pyrimidine Derivatives

Stéphane Massipa, Jean Guillon*a, Pascal Sonnetb, Jean-Michel Légera, Jean-Jacques Bosca, Christa E. Müllerc, Christian Jarrya
a EA 4138 - Pharmacochimie, UFR des Sciences Pharmaceutiques, Université Victor Segalen Bordeaux 2, 146 rue Léo Saignat, 33076 Bordeaux Cedex, France
Fax: +33(5)57571352; e-Mail: Jean.Guillon@chimphys.u-bordeaux2.fr;
b EA 3901 - DMAG, Faculté de Pharmacie, Université de Picardie Jules Verne, 1 rue des Louvels, 80037 Amiens Cedex 1, France
c Universität Bonn, Pharmazeutisches Institut, Pharmazeutische Chemie, Poppelsdorf, Kreuzbergweg 26, 53115 Bonn, Germany
Further Information

Publication History

Received 21 March 2007
Publication Date:
03 July 2007 (online)

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Abstract

8-(Dimethylamino)-3-(2-hydroxy-3-phenoxypropyl)­-xanthine has been obtained from 6-amino-1-(2-hydroxy-3-phen­oxypropyl)uracil by an azodicarboxylate Michael-type addition involving a reactive diene. 6-Amino-1-(2-hydroxy-3-phenoxy­-propyl)uracil was easily prepared from racemic 2-amino-5-(phen­oxymethyl)-2-oxazoline. Moreover, these chemical investigations also led to the identification of a racemic 7-aminooxazolo[5,4-d]pyrimidin-5(6H)-one, obtained by the condensation reaction of the phosgeniminium chloride, Viehe’s salt, with 5,6-diamino-1-(2-hydroxy-3-phenoxypropyl)uracil.

Key words

bicyclic compounds - ene reactions - uracils - fused-ring systems - Michael additions

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