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■ [4+2] Cycloaddition Reactions between 2,4-Diamino-1-thia-3-azabutadienes and Ketene. Synthesis of New 1,3-Thiazin-6-ones, 1,3-Thiazine-6-thiones and 2-Thioxopyrimidin-4-ones

Cyrille Landreau, David Deniaud, Françoise Reliquet, Alain Reliquet, and Jean Claude Meslin*

*Laboratoire de Synthèse Organique, UMR, C.N.R.S. 6513, Faculté des Sciences et des Techniques, Université de Nantes, 2, rue de la Houssiniere, 44072 Nantes Cedex, France

Abstract

The reaction of 2,4-diamino-1-thia-3-azabutadienes with an excess of ketene afforded 2-amino-1,3-thiazin-6-ones and 2-thioxopyrimidin-4-ones by [4+2] cycloaddition reaction. Reaction between thiazabutadienes and ketene gave rise to aminothiazinones, which were sulfured by action of phosphorus pentasulfide leading to aminothiazinethiones. Furthermore, synthesis of thioxopyrimidinones starting from S-methyl salts of thiazadienes is described.