2H-1,2,4,6-thiatriazin-3(4H)-one 1-oxides and their regioselective N4-methylation and -amination |
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Authors: | Yoshinori Nakayama Yuzuru Sanemitsu |
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Institution: | Pesticides Research Laboratory, Takarazuka Research Center, Sumitomo Chemical Co., Ltd., Takarazuka, Hyogo 665, Japan |
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Abstract: | The syntheses of 2H-1,2,4,6-thiatriazin-3(4H)-one 1-oxides and 1,1-dioxides is described. The reaction of 1-carbamoyl-2-methylisothioureas 2 with thionyl chloride gave 2H-1,2,4,6-thiatriazin-3(4H)-one 1-oxides 3 in high yields. The treatment of 3 with either diazomethane or O-(2,4-dinitrophenyl)hydroxylamine furnished regioselectively N4-methylated and N4-aminated 2H-1,2,4,6-thiatriazin-3(4H)-one 1-oxides, respectively. Subsequent dimethylamination of 4 followed by oxidation with m-chloroperoxybenzoic acid led to 2H-1,2,4,6-thiatriazin-3(4H)-one 1,1-dioxides 6a-c . |
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