3'-amino-5-chloro-2,5',10'-trioxo-5',10'-dihydrospiro [indoline-3,1'-pyrazolo[1,2-b]phthalazine]-2'-carbonitrile | 1334175-97-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3'-amino-5-chloro-2,5',10'-trioxo-5',10'-dihydrospiro [indoline-3,1'-pyrazolo[1,2-b]phthalazine]-2'-carbonitrile
• 英文别名: 1'-amino-6-chloro-2,5',10'-trioxospiro[1H-indole-3,3'-pyrazolo[1,2-b]phthalazine]-2'-carbonitrile
• CAS: 1334175-97-1
• 化学式: C₁₉H₁₀ClN₅O₃
• 分子量: 391.773
• InChiKey: OFWHPLNUVJQRIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯酐 、 6-氯靛红 、 丙二腈 在 肼 作用下， 以 neat (no solvent) 为溶剂， 反应 0.83h， 以91%的产率得到3'-amino-5-chloro-2,5',10'-trioxo-5',10'-dihydrospiro [indoline-3,1'-pyrazolo[1,2-b]phthalazine]-2'-carbonitrile
  参考文献：
  名称：

  Methylene dipyridine nanoparticles stabilized on Fe3O4 as catalysts for efficient, green, and one-pot synthesis of pyrazolophthalazinyl spirooxindoles

  摘要：

  Surface functionalization of magnetic particles is an elegant way to bridge the gap between heterogeneous and homogeneous catalysis. The introduction of magnetic particles (MPs) in a variety of solid matrices allows the combination of well-known procedures for catalyst heterogenization with techniques for magnetic separation. We have conveniently loaded base groups on magnetic particles supports in which dipyridin-2-ylmethanol is used as aminating agent. The main targets are room temperature, solvent-free conditions, rapid (immediately) and easy immobilization technique, and low cost precursors for the preparation of highly active and stable MPs with high densities of functional groups. The inorganic, magnetic, solid base catalyst was characterized via Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), transmission electron microscopy (TEM) and vibrating sample magnetometer (VSM). The catalyst is active for the synthesis of pyrazolophthalazinyl spirooxindoles and the products are isolated in high to excellent yields (90-93%). Supporting this base catalyst on magnetic particles offers a simple and non-energy-intensive method for recovery and reuse of the catalyst by applying an external magnet. Isolated catalysts were reused for new rounds of reactions without significant loss of their catalytic activity. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.cattod.2013.07.018

文献信息

• Nickel chloride-catalyzed one-pot three-component synthesis of pyrazolophthalazinyl spirooxindoles
  作者：Xiao-Nan Zhang、Yong-Xiao Li、Zhan-Hui Zhang

  DOI：10.1016/j.tet.2011.07.002

  日期：2011.9

  A direct and efficient approach for the preparation of pyrazolophthalazinyl spirooxindoles has been developed through one-pot three-component reaction of easily available isatin, malononitrile or cyanoacetic ester, and phthalhydrazide catalyzed by nickel chloride in polyethylene glycol 600. Desired products were obtained in high to excellent yields using a simple workup procedure.

  通过易得的靛红，丙二腈或氰基乙酸酯与邻苯二甲酰肼在聚乙二醇600中由氯化镍催化的一锅式三组分反应，已经开发出一种直接有效的方法来制备吡唑并酞菁螺并辛酯。使用简单的后处理程序即可获得出色的产量。