3-methyl-1-phenyl-4,11-dihydrospiro[1H-pyrazolo[3,4-b]benzo[h]quinoline-4,3'-indolin]-2'-one | 1562075-84-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-1-phenyl-4,11-dihydrospiro[1H-pyrazolo[3,4-b]benzo[h]quinoline-4,3'-indolin]-2'-one
• 英文别名: 8-Methyl-10-phenyl-10,11-dihydrospiro[pyrazolo[3,4-b]benzo[h]quinolin-7,3'-indol]-2'(1'h)-one；13-methyl-15-phenylspiro[14,15,17-triazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,8,12(16),13-heptaene-11,3'-1H-indole]-2'-one
• CAS: 1562075-84-6
• 化学式: C₂₈H₂₀N₄O
• 分子量: 428.493
• InChiKey: KOPJSZKESBEXON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  59
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  靛红 、 1-萘胺 、 依达拉奉 在 对甲苯磺酸 作用下， 以 neat (no solvent) 为溶剂， 反应 1.67h， 以81%的产率得到3-methyl-1-phenyl-4,11-dihydrospiro[1H-pyrazolo[3,4-b]benzo[h]quinoline-4,3'-indolin]-2'-one
  参考文献：
  名称：

  A four-component synthesis of novel spiro[pyrazoloquinoline-oxindoles] under solvent-free conditions

  摘要：

  A domino reaction for the rapid and diverse synthesis of spiro[1H-pyrazolo[3,4-b]benzo[h]dihydroquinolin-4,3-indolin-2-ones] is reported. The synthesis represents a thermodynamically-favored four-component reaction between phenylhydrazine, isatins, naphthylamines, and 3-ketoesters giving the novel products in excellent yields under solvent-free conditions. Similar applications of anilines in place of naphthylamines have not led to formation of the expected 4-substituted pyrazolo[3,4-b]quinoline derivatives. The difference was ascribed to lower aromatic character of naphthylamines, with respect to anilines, which enables them to act easier as enamines in reaction with the postulated intermediates formed from condensation of isatins and the in situ generated pyrazolones. Surprisingly, 6-aminouracils in despite of their known enamine properties did not participate in reaction with isatins and pyrazolones, the merit of naphthylamines for this synthesis seems to be met by the favorable balance of their N- and C-nucleophilicity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.01.025

文献信息

• Synthesis of spiro-oxindoles catalyzed by nano-Co3S4
  作者：Hossein Shahbazi-Alavi、Fatemeh Alemi-Tameh、Javad Safaei-Ghomi

  DOI：10.1007/s00706-018-2246-3

  日期：2018.11

  AbstractA simple method for the synthesis of spiro[pyrazoloquinoline-oxindoles] and spiro[chromenopyrazolo-oxindoles] has been achieved through four-component reactions of phenylhydrazine or hydrazine hydrate, isatins, ketoesters, and naphthylamine or 2-naphthol using nano-Co3S4 under ultrasonic irradiations. The current method provides obvious positive points such as environmental friendliness, significantly

  摘要通过使用纳米Co 3 S通过苯肼或肼水合物，靛红，酮酸酯和萘胺或2-萘酚的四组分反应，已经实现了一种简单的合成吡咯并吡咯并喹啉和吲哚并吡咯并喹啉的方法。4在超声波照射下。当前的方法提供了明显的积极点，例如环境友好，显着缩短的反应时间，显着优异的收率和简单的后处理程序。 图形概要
• Synthesis of spiro[pyrazoloquinoline-oxindoles] and spiro[chromenopyrazolo-oxindoles] promoted by guanidine-functionalized magnetic Fe3O4 nanoparticles
  作者：Fatemeh Alemi Tameh、Javad Safaei-Ghomi

  DOI：10.1007/s13738-018-1361-8

  日期：2018.7

  MNPs-guanidine) have been used as an efficient catalyst for the preparation of spiro[pyrazoloquinoline-oxindoles] and spiro[chromenopyrazolo-oxindoles] by four-component reactions of phenylhydrazine or hydrazine hydrate, isatins, ketoesters and naphthylamine or 2-naphthol under reflux condition in ethanol. This method provides several advantages including mild reaction conditions, the applicability to

  磁性纳米粒子（MNPs）固定有Fe 3 O 4的胍（Fe 3 O 4 MNPs-胍）是通过四组分反应制备螺并[吡唑并喹啉-恶唑]和螺[并吡喃并吡咯并恶唑]的有效催化剂。在乙醇中回流条件下制备苯肼或肼水合物，靛红，酮酸酯和萘胺或2-萘酚。该方法具有几个优点，包括温和的反应条件，适用于多种底物，催化剂的可重复使用性和低的催化剂载量。