HETEROCYCLES

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■ Reaction of 5-Substituted 2-Amino-2-oxazolines with Ethoxycarbonyl Isothiocyanate

Christian Jarry,* Isabelle Forfar, Jacqueline Thomas, Jean Michel Leger, and Michel Laguerre

*Groupe de Recherche d’Hétérocycles à Potentialités Thérapeutiques, Université de Bordeaux II, 33076 Bordeaux Cedex, France

Abstract

The reaction of 2-amino-2-oxazolines with ethoxycarbonyl isothiocyanate was found to give only 2,3,6,7-tetrahydro-4H-oxazolo[3,2-a]-1,3,5-triazin-2-one-4-thiones, the structure of which was confirmed by X-ray crystallographic analysis. The direction of attack seems to be related to the more potent nucleophilic character of the endo nitrogen atom in 2-amino-2-oxazoliens. In basic conditions the oxazoline ring can be easily hydrolyzed leading to 1-substituted 1,3,5-triazin-2,4-dione-6-thione.