6-氨基-5-氰基-3-甲基-4-(4-硝基苯基)-1-苯基吡唑并[3,4-b]吡啶 | 258340-68-0

• 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
• 中文名称: 6-氨基-5-氰基-3-甲基-4-(4-硝基苯基)-1-苯基吡唑并[3,4-b]吡啶
• 英文名称: 6-amino-3-methyl-4-(4-nitrophenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile
• 英文别名: 6-amino-4-(4-nitrophenyl)-5-cyano-3-methyl-1-phenyl-1H-pyrazolo[3,4-b] pyridine；6-amino-5-cyano-3-methyl-4-(4-nitrophenyl)-1-phenylpyrazolo[3,4-b]pyridine；6-amino-5-cyano-4-(4-nitrophenyl)-3-methyl-1-phenylpyrazolo[3,4-b]pyridine；6-amino-3-methyl-4-(4-nitrophenyl)-1-phenylpyrazolo[3,4-b]pyridine-5-carbonitrile
• CAS: 258340-68-0
• 化学式: C₂₀H₁₄N₆O₂
• 分子量: 370.37
• InChiKey: PFFXQLFINNPKJP-UHFFFAOYSA-N

物化性质

• 熔点：
  215-217 °C(Solv: ethanol (64-17-5))
• 沸点：
  610.5±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-氨基-3-甲基-1-苯基吡唑 、 1,1-二氰基-2-(-p-硝基苯基)-乙烯 在 sodium 1-dodecylsulfate 作用下， 以 水 为溶剂， 反应 5.0h， 以73%的产率得到6-氨基-5-氰基-3-甲基-4-(4-硝基苯基)-1-苯基吡唑并[3,4-b]吡啶
  参考文献：
  名称：

  水介质中吡唑并[3,4-b]吡啶衍生物的高效合成

  摘要：

  5-氨基吡唑与亚苄基丙二腈在水介质中反应合成了一系列吡唑并[3,4-b]吡啶。结构通过 IR、1H NMR 和元素分析进行​​表征，并通过 X 射线衍射分析进一步证实。

  DOI：

  10.1002/jccs.200700190

文献信息

• Synthesis and application of a novel nanomagnetic catalyst with Cl[DABCO-NO2]C(NO2)3 tags in the preparation of pyrazolo[3,4-b]pyridines via anomeric based oxidation
  作者：Javad Afsar、Mohammad Ali Zolfigol、Ardeshir Khazaei、Diego A. Alonso、Abbas Khoshnood、Yadollah Bayat、Asiye Asgari

  DOI：10.1007/s11164-018-3576-9

  日期：2018.12

  A novel nanomagnetic catalyst with Cl[DABCO-NO2]C(NO2)3 tags was designed, synthesized and fully characterized by several techniques such as Fourier transform infrared spectroscopy, energy-dispersive X-ray spectroscopy, elemental mapping analysis, thermogravimetric analysis, derivative thermal gravimetric, powder X-ray diffraction patterns, field scanning electron microscopy, high resolution transmission

  设计并合成了具有Cl [DABCO-NO 2 ] C（NO 2）3标签的新型纳米磁性催化剂，并通过傅里叶变换红外光谱，能量色散X射线光谱，元素图谱分析，热重分析等多种技术对其进行了表征。 ，导数热重分析，粉末X射线衍射图，场扫描电子显微镜，高分辨率透射电子显微镜，N 2等温线（BET）的物理吸附和解吸以及振动样品磁力计。将合成的纳米磁性颗粒被用作的3-甲基-1-苯基-1-一锅三个组分缩合反应的高效和可回收催化剂 ħ -吡唑-5-胺或3-甲基-1 H- 吡唑-5-胺，芳基醛和丙二腈在纯净条件下合成吡唑并[3,4- b ]-吡啶衍生物。
• Controllable Synthesis of Pyrazolo[3,4-b]pyridines or Substituted Malononitrile Derivatives through Multi-Component Reactions in Ionic Liquid
  作者：Xinying Zhang、Xiaoyan Li、Xuesen Fan、Xia Wang、Jianji Wang、Guirong Qu

  DOI：10.1071/ch08290

  日期：——

  A multi-component reaction of aldehyde, malononitrile, and 5-amino-3-methyl-1-phenylpyrazole was carried out smoothly in [bmim][BF4] without any added catalyst. Through this reaction, pyrazolo[3,4-b]pyridines or substituted malononitrile derivatives were obtained conveniently and controllably at different temperatures. The ionic liquid used can be easily recovered and efficiently reused for at least

  醛，丙二腈和5-氨基-3-甲基-1-苯基吡唑的多组分反应在[bmim] [BF 4 ]中平稳进行，无需添加任何催化剂。通过该反应，可方便地，可控制地在不同温度下获得吡唑并[3，4- b ]吡啶或取代的丙二腈衍生物。所使用的离子液体可轻松回收并有效重复使用至少五次。
• Synthesis of 5-cyanopyrazolo[3,4-<i>b</i>]pyridines in the reaction of 5-amino-3-methyl-1-phenylpyrazole with arylidene derivatives of malonodinitrile and ethyl cyanoacetate
  作者：Jairo Quiroga、Mario Alvarado、Braulio Insuasty、Rodolfo Moreno、Enrique Raviña、Isabel Estevez、Regina H. De Almeida S.

  DOI：10.1002/jhet.5570360533

  日期：1999.9

  This paper describes the synthesis of a new series of 6-amino-4-aryl-5-cyanopyrazolo[3,4-b]pyridines 4 and 4-aryl-5-cyano-6H-pyrazolo[3,4-b]pyridin-6-ones 5 from the reaction of 5-amino-3-methyl-1-phenylpyrazole 1 with arylidene derivatives of malonodinitrile 2 and ethyl cyanoacetate 3. The structure of the final compounds was determined on the basis of nmr measurements, especially by 1H, 1H-, 1H,

  本文描述了一系列新的6-氨基-4-芳基-5-氰基吡唑并[3,4的合成b ]吡啶化合物4和4-芳基-5-氰基-6- ħ -吡唑并[3,4- b ] 5-氨基-3-甲基-1-苯基吡唑1与丙二醛2的芳基衍生物和氰基乙酸乙酯3反应生成的吡啶-6-酮5。最终化合物的结构是根据nmr测量确定的，尤其是通过1 H，1 H-，1 H，13 C-COSY，DEPT和X射线衍射确定的。
• A simple and efficient preparation of pyrazolo[3,4-<i>b</i>]-pyridine derivatives through an unexpected reaction of cyanothioacetamide under microwave irradiation
  作者：Xuesen Fan、Xia Wang、Xinying Zhang、Xiaoyan Li、Guirong Qu

  DOI：10.1002/hc.20497

  日期：2008.11

  An unexpected multicomponent reaction of cyanothioacetamide with aromatic aldehydes and aminopyrazole under MWI was found and reported. It turned out to be an efficient and simple procedure for the preparation of pyrazolo[3,4-b]pyridine derivatives. The structure of the product was characterized by IR, MS, 1H and 13C NMR, COSY and NOESY spectroscopy, X-ray crystallographic analysis, and by comparison

  发现并报道了氰硫代乙酰胺与芳香醛和氨基吡唑在 MWI 下的意外多组分反应。结果证明这是制备吡唑并[3,4-b]吡啶衍生物的一种有效且简单的方法。产物的结构通过IR、MS、1H和13C NMR、COZY和NOESY光谱、X-射线晶体学分析以及与用已知方法制备的真实样品进行比较来表征。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:694–699, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20497
• Three‐Component, One‐Pot Synthesis of Pyrazolo[3,4‐<i>b</i>]pyridine Derivatives in Aqueous Media
  作者：Da‐Qing Shi、Hao Yao、Jing‐Wen Shi

  DOI：10.1080/00397910801929804

  日期：2008.4.1

  6-Amino-4-aryl-5-cyanopyrazolo[3,4-b]pyridines were synthesized by a three-component reaction of aromatic aldehydes, malononitrile, and 5-amino-3methyl-1-phenylpyrazole using sodium 1-dodecanesulfonic (SDS) as catalyst in aqueous media. The reaction has the advantages of good yields, less pollution, ease of separation, and environmental friendliness.