4,6-dinitro-1-phenyl-1H-indazole-3-carboxaldehyde N-phenylhydrazone | 545357-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,6-dinitro-1-phenyl-1H-indazole-3-carboxaldehyde N-phenylhydrazone
• 英文别名: N-[(4,6-dinitro-1-phenylindazol-3-yl)methylideneamino]aniline
• CAS: 545357-61-7
• 化学式: C₂₀H₁₄N₆O₄
• 分子量: 402.369
• InChiKey: PWXTXOSBFLVOFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  128.49
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4,6-dinitro-1-phenyl-1H-indazole-3-carboxaldehyde N-phenylhydrazone 在 N-甲基吡咯烷酮 、 potassium carbonate 作用下， 反应 10.0h， 以47%的产率得到7-nitro-1,5-diphenyl-1,5-dihydropyrazolo[3,4,5-de]cinnoline
  参考文献：
  名称：

  Synthesis of 14π-electron peri-annelated tricyclic heteroaromatic systems based on 2,4,6-trinitrotoluene

  摘要：

  Methyl 1-aryl-7-nitro-1H-thiopyrano[4,3,2-cd]indazol-4-carboxylates 2 and 1,5-diaryl-7-nitro-1,5-dihydropyrazolo[3,4,5-de]-cinnolines 4 were prepared based on 1-aryl-3-formyl-4,6-dinitro-1H-indazoles 1, which were synthesised previously starting from 2,4,6-trinitrotoluene.

  DOI：

  10.1070/mc2002v012n05abeh001642
• 作为产物：
  描述：

  苯肼 、 3-formyl-4,6-dinitro-1-phenyl-1H-indazole 以 乙醇 为溶剂， 反应 3.0h， 以74%的产率得到4,6-dinitro-1-phenyl-1H-indazole-3-carboxaldehyde N-phenylhydrazone
  参考文献：
  名称：

  Synthesis of 14π-electron peri-annelated tricyclic heteroaromatic systems based on 2,4,6-trinitrotoluene

  摘要：

  Methyl 1-aryl-7-nitro-1H-thiopyrano[4,3,2-cd]indazol-4-carboxylates 2 and 1,5-diaryl-7-nitro-1,5-dihydropyrazolo[3,4,5-de]-cinnolines 4 were prepared based on 1-aryl-3-formyl-4,6-dinitro-1H-indazoles 1, which were synthesised previously starting from 2,4,6-trinitrotoluene.

  DOI：

  10.1070/mc2002v012n05abeh001642

文献信息

• ——
  作者：A. M. Starosotnikov、A. V. Lobach、V. M. Vinogradov、S. A. Shevelev

  DOI：10.1023/a:1026056704860

  日期：——

  A method for the synthesis of peri-annelated trinuclear heterocycles, including 14pi-electron heteroaromatic systems, namely, 1H-thiopyrano[4,3,2-cd]indazoles and 1,5-dihydropyrazolo[3,4,5-de]cinnolines, from 3-R-1-aryl-4,6-dinitro-1H-indazoles was developed. The method is based on the high mobility of the NO2 group in position 4 and consists of either selective nucleophilic substitution of the 4-NO2 group on treatment with the HSCH2CO2Me-K2CO3 system followed by intramolecular cyclization of the resulting sulfide (R = CHO) or the corresponding sulfone (R = CN) formed upon its oxidation or direct intramolecular substitution of the 4-NO2 group (R = CH=NNH Ph).