5-benzylamino-3-methylthio-as-triazine | 84582-96-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-benzylamino-3-methylthio-as-triazine
• 英文别名: 6-amino-5-benzylamino-3-methylsulfanyl-1,2,4-triazine；5-Benzylamino-6-amino-3-(methylthio)-as-triazine；5-N-benzyl-3-methylsulfanyl-1,2,4-triazine-5,6-diamine
• CAS: 84582-96-7
• 化学式: C₁₁H₁₃N₅S
• 分子量: 247.324
• InChiKey: PRVYOVVFQUTYST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-benzylamino-3-methylthio-as-triazine 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以75%的产率得到6-amino-5-benzylamino-3-methylsulfonyl-1,2,4-triazine 1-oxide
  参考文献：
  名称：

  Condensed 1,2,4-triazines: synthesis of 5- benzyl-5H-imidazo[4,5-e]-1,2,4-triazine 1-oxides (9-benzyl-6-azapurine 6-oxides)

  摘要：

  A number of 5-benzyl-5H-imidazo[4,5-e]-1,2,4-triazine 1-oxides, bioisosteric isomers of antiviral 9-benzylpurines, have been prepared. Oxidation of 6-amino-5-benzylamino-3-methylsulfanyl-1,2,4-triazine 1 with excess of m-chloroperbenzoic acid afforded 6-amino-5-benzylamino-3-methylsulfonyl-1,2,4-triazine 1-oxide 2 in 75% yield. The 3-methylsulfonyl group, which is a good leaving group, has been replaced with various nucleophiles to give 3-amino 4, 3-methoxy 5 and 3-hydrazino 8 derivatives. Oxidative dehydrazination of 8 with mercury(II) oxide (HgO) in ethanol gave 6-amino-5-benzylamino-1,2,4-triazine 1-oxide 9 in a moderate yield. The 1,2,4-triazine 1-oxides were then cyclized with triethyl orthoformate (TEOF) to afford the title compounds in 28-88% yields.

  DOI：

  10.1039/p19940002253
• 作为产物：
  描述：

  3,5-二(甲硫基)-1,2,4-三嗪-6-胺 、 苄胺 反应 12.0h， 以86%的产率得到5-benzylamino-3-methylthio-as-triazine
  参考文献：
  名称：

  Synthesis of certain 5,6-diamino-as-triazines: precursors for fused heterocyclic systems

  摘要：

  DOI：

  10.1021/jo00156a025

文献信息

• Tzeng Cherng-Chyi, Wei Dau-Chang, Hwang Long-Chih, Cheng Ming-Chu, Wang Y+, J. Chem. Soc. Perkin Trans. 1, (1994) N 16, S 2253-2256
  作者：Tzeng Cherng-Chyi, Wei Dau-Chang, Hwang Long-Chih, Cheng Ming-Chu, Wang Y+

  DOI：——

  日期：——
• TZENG, CHERNG-CHYI;MOTOLA, N. C.;PANZICA, R. P., J. ORG. CHEM., 1983, 48, N 8, 1271-1275
  作者：TZENG, CHERNG-CHYI、MOTOLA, N. C.、PANZICA, R. P.

  DOI：——

  日期：——
• Hwang, Long-Chih; Wei, Dau-Chang; Han, Chein-Hwa, Journal of Chemical Research, Miniprint, 1994, # 4, p. 831 - 842
  作者：Hwang, Long-Chih、Wei, Dau-Chang、Han, Chein-Hwa、Lee, Kuan-Han、Tzenga, Cherng-Chyi

  DOI：——

  日期：——
• Synthesis of certain 5,6-diamino-as-triazines: precursors for fused heterocyclic systems
  作者：Cherng Chyi Tzeng、Nancy C. Motola、Raymond P. Panzica

  DOI：10.1021/jo00156a025

  日期：1983.4
• Condensed 1,2,4-triazines: synthesis of 5- benzyl-5H-imidazo[4,5-e]-1,2,4-triazine 1-oxides (9-benzyl-6-azapurine 6-oxides)
  作者：Cherng-Chyi Tzeng、Dau-Chang Wei、Long-Chih Hwang、Ming-Chu Cheng、Yu Wang

  DOI：10.1039/p19940002253

  日期：——

  A number of 5-benzyl-5H-imidazo[4,5-e]-1,2,4-triazine 1-oxides, bioisosteric isomers of antiviral 9-benzylpurines, have been prepared. Oxidation of 6-amino-5-benzylamino-3-methylsulfanyl-1,2,4-triazine 1 with excess of m-chloroperbenzoic acid afforded 6-amino-5-benzylamino-3-methylsulfonyl-1,2,4-triazine 1-oxide 2 in 75% yield. The 3-methylsulfonyl group, which is a good leaving group, has been replaced with various nucleophiles to give 3-amino 4, 3-methoxy 5 and 3-hydrazino 8 derivatives. Oxidative dehydrazination of 8 with mercury(II) oxide (HgO) in ethanol gave 6-amino-5-benzylamino-1,2,4-triazine 1-oxide 9 in a moderate yield. The 1,2,4-triazine 1-oxides were then cyclized with triethyl orthoformate (TEOF) to afford the title compounds in 28-88% yields.