2H-1,2,4,6-THIATRIAZIN-3(4H)-ONE 1-OXIDES AND THEIR REGIOSELECTIVE N4-METHYLATION AND N4-AMINATION
2H-1,2,4,6-THIATRIAZIN-3(4H)-ONE 1-OXIDES AND THEIR REGIOSELECTIVE N4-METHYLATION AND N4-AMINATION
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DOI：
10.1002/jhet.5570210562
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发表时间：
1984-01-01
影响因子：
2.4
通讯作者：
SANEMITSU, Y
中科院分区：
文献类型：
--
作者：
NAKAYAMA, Y;SANEMITSU, Y
描述了 2H-1,2,4,6-thiatriazin-3(4H)-one 1-氧化物和 1,1-二氧化物的合成。 1-氨基甲酰基-2-甲基异硫脲2与亚硫酰氯反应以高产率得到2H-1,2,4,6-噻三嗪-3(4H)-酮1-氧化物3。用重氮甲烷或O-(2,4-二硝基苯基)羟胺处理3分别得到区域选择性N4-甲基化和N4-胺化的2H-1,2,4,6-噻三嗪-3(4H)-酮1-氧化物。随后将4进行二甲基胺化，然后用间氯过苯甲酸氧化，得到2H-1,2,4,6-噻三嗪-3(4H)-酮1,1-二氧化物6a-c。 [这些化合物具有植物毒性，可作为除草剂使用。]
The synthesis 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. [These compounds have phytotoxic properties which are of interest as herbicides.].