1,2,4-三嗪类化合物的研究——XXI.3-甲硫基-5-氧代-2,5-二氢-1,2,4-三嗪的取代苯磺酰化反应及6-碳的亲电特性

Chemistry of 1,2,4-Triazines XXI. The Substituted Benzene Sulfonation and Properties of Electrophilic Addition in 6-Carbon of 3-Methylthio-5-oxo-2,5-dihydro-1,2,4-triazine

3-甲硫基-5-氧代-2,5-二氢-1,2,4-嗪(lc)与取代的苯磺酰氯反应,在无水吡啶中生成N-[6-(3-甲硫基-5-负氧基)-1,2,4-三嗪基]吡啶内(钅翁)盐(4);在NaOH-H_(2)O-CH_(3)COCH_(3)中生成3-甲硫基-4-(取代苯磺酰基)-5-氧代-6-羟基-1,4,5,6-四氢-1,2,4-三嗪(6);在NaOH-CH_3OH中则生成1-(对甲苯磺酰基)-3-甲硫基-5-氧代-6-甲氧基-1,4,5,6-四氢-1,2,4-三嗪(7),显示了其6-C具有不寻常的亲电特性.

3-Methylthio-5-oxo-2,5-dihydro-l,2,4-triazine reacted with substitued benzene sulfochloride, to give 3-methylthio-4-substituted benzene sulfonyl-5-oxo-6-hydroxy-1,4, 5,6-tetrahydro-l,2,4-triazine in the solution of NaOH-H2O-CH3COCH3; to give 1-tosyl-3-methylthio-5-oxo-6-methyloxy-l,4,5,6-tetrahydro-l,2,4-triazine in the solution of NaOH-CH3OH. The series of reaction show a anomalous properties of electrophilic addition in 6-carbon of the 1,2,4-triazine ring.