Preparation and Reactions of 4-Alkoxy-6-amino-2H-1, 3, 5-thiadiazine-2-thiones

Abstract

4-Alkoxy-6-amino-2 H-1, 3, 5-thiadiazine-2-thiones 5 J were prepared by the reaction of N'-cyano-O-alkylisourea [4] with carbon disulfide in the presence of potas sium hydroxide, f ollowed by acidification. Thiadiazine [5 a] (R=Et) rearranged into 6-ethoxy-1, 3, 5-triazine-2, 4(1 H, 3 H)-dithione [9] in ethanolic sodium hydroxide, whereas yielded dimethyl N-a(cyanoimino)ethoxymethyljimidodithiocarbonate [3 ] by the reacti on of methyl iodide in the presence of potassium hydroxide. Heating of 5 in water resulted in the hydrolysis at 4-position of thiadiazine ring and N'-(alkoxycarbonyl)thioureas [10] were obtained.
6-Amino-4-(substituted amino)-1, 3, 5-2 H-thiadiazine-2-thione 1 could b e obtained by the reaction of [5 a] with amines, and the reactivity of [1] was also investigated.