6-amino-3-methyl-4-(2-nitrophenyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile | 1313199-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-amino-3-methyl-4-(2-nitrophenyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile
• 英文别名: 6-amino-3-methyl-4-(2-nitrophenyl)-2H-pyrazolo[3,4-b]pyridine-5-carbonitrile
• CAS: 1313199-48-2
• 化学式: C₁₄H₁₀N₆O₂
• 分子量: 294.272
• InChiKey: FYDDFTUADRLOLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  137
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  邻硝基苯甲醛 以 乙醇 为溶剂， 生成 6-amino-3-methyl-4-(2-nitrophenyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile
  参考文献：
  名称：

  Convenient Ultrasound-Promoted Regioselective Synthesis of Fused 6-Amino-3-methyl-4-aryl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

  摘要：

  [image omitted] A multicomponent, catalyst-free reaction for the synthesis of fused 6-amino-3-methyl-4-aryl-1H-pyrazolo [3,4-b] pyridine-5-carbonitrile from 3-amino-5-methylpyrazole, malononitrile, and substituted aldehydes under ultrasound irradiation in short reaction times (8-10min) with good yields (85-98%) is reported.

  DOI：

  10.1080/00397911.2010.502990

文献信息

• Catalyst-free grinding method: a new avenue for synthesis of 6-amino-3-methyl-4-aryl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile and DFT studies on the mechanistic pathway of this category of compounds
  作者：Mohammad Nikpassand、Leila Zare Fekri、Parissa Naddaf Rahro

  DOI：10.1007/s11164-018-3701-9

  日期：2019.4

  A novel, efficient, one-pot, catalyst-free grinding procedure for synthesis of 6-amino-3-methyl-4-aryl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile is reported. The condensation of substituted benzaldehydes, 3-amino-5-methylpyrazole, and malononitrile according to a three-component reaction was investigated using density functional theory (DFT) at B3LYP/6-311G level to explore the reaction mechanism.

  报道了一种新颖，高效，一锅无催化剂的研磨程序，用于合成6-氨基-3-甲基-4-芳基-1 H-吡唑并[3,4- b ]吡啶-5-甲腈。利用密度泛函理论（DFT）在B3LYP / 6-311G水平上研究了取代的苯甲醛，3-氨基-5-甲基吡唑和丙二腈根据三组分反应的缩合反应，探讨了其反应机理。研究了所有路线，优化了中间体的结构，并找到了所有的过渡态。计算结果表明，所提出的机制依赖于四个中间体。
• Aluminum hydrogen sulfate as a green catalyst for the solvent-free synthesis of pyrazolopyridines
  作者：M. Nikpassand、L. Zare Fekri

  DOI：10.1134/s1070363215050308

  日期：2015.5

  Aluminum hydrogen sulfate turned out to be a mild, convenient, and efficient reagent for the conversion of substituted benzyl alcohols into pyrazolopyridines via condensation with 3-methyl-1H-pyrazole-5-amine and CH acid (malononitrile or indan-1,3-dione) at room temperature under solvent-free conditions with high yield, high purity, and short reaction time.