6-amino-5-benzylamino-1,2,4-triazine 1-oxide | 159554-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-amino-5-benzylamino-1,2,4-triazine 1-oxide
• CAS: 159554-20-8
• 化学式: C₁₀H₁₁N₅O
• 分子量: 217.23
• InChiKey: HCBKNOCQMCPKQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  90.77
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-amino-5-benzylamino-1,2,4-triazine 1-oxide 、 原甲酸三乙酯 在 盐酸 作用下， 反应 2.0h， 以65%的产率得到5-benzyl-5H-imidazo<4,5-e>-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：

  6-amino-5-benzylamino-3-methylsulfonyl-1,2,4-triazine 1-oxide 在 mercury(II) oxide 、 肼 作用下， 以 乙醇 为溶剂， 反应 29.0h， 生成 6-amino-5-benzylamino-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

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：——
• 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.