1',3',8',8'-tetramethyl-8',9'-dihydro-1'H-spiro[indoline-3,5'-pyrimido[4,5-b]quinoline]-2,2',4',6'(3'H,7'H,10'H)-tetraone | 1422371-94-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 1',3',8',8'-tetramethyl-8',9'-dihydro-1'H-spiro[indoline-3,5'-pyrimido[4,5-b]quinoline]-2,2',4',6'(3'H,7'H,10'H)-tetraone
• 英文别名: 1',3',8',8'-Tetramethyl-8',9'-dihydro-1'h-spiro[indoline-3,5'-pyrimido[4,5-b]quinoline] 2,2',4',6'(3'h,7'h,10'h)-tetraone；1',3',8',8'-tetramethylspiro[1H-indole-3,5'-9,10-dihydro-7H-pyrimido[4,5-b]quinoline]-2,2',4',6'-tetrone
• CAS: 1422371-94-5
• 化学式: C₂₂H₂₂N₄O₄
• 分子量: 406.441
• InChiKey: JMVUCNWYCSJVIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-二甲基-6-氨基脲嘧啶 、 靛红 、 5,5-二甲基-1,3-环己二酮 在 Pd immobilized on the modified mesoporous silica SBA-15 作用下， 以 水 为溶剂， 反应 0.25h， 以94%的产率得到1',3',8',8'-tetramethyl-8',9'-dihydro-1'H-spiro[indoline-3,5'-pyrimido[4,5-b]quinoline]-2,2',4',6'(3'H,7'H,10'H)-tetraone
  参考文献：
  名称：

  Sonosynthesis of spiroindolines using functionalized SBA-15

  摘要：

  功能化SBA-15（在修饰的SBA-15上固定钯）已被用作通过异吲哚酮、环状-1,3-二酮和6-氨基-1,3-二甲基尿嘧啶在水中超声辐照下的多组分反应高效制备螺环吲哚啉的催化剂。该催化剂通过X射线衍射光谱（XRD）、场发射扫描电子显微镜（FE-SEM）、透射电子显微镜（TEM）、能谱X射线光谱（EDX）、X射线光电子光谱（XPS）、傅里叶变换红外光谱（FT-IR）、氮气吸附分析、程序升温脱附（TPD）和热重分析（TGA）进行了表征。该方法的优势包括催化剂的可重复使用性、低催化剂负载量、短时间内优异的产率、产品易于分离以及将超声辐照作为一项有价值且强大的技术。

  DOI：

  10.1007/s11164-021-04506-7

文献信息

• Magnetic, Acidic, Ionic Liquid-Catalyzed One-Pot Synthesis of Spirooxindoles
  作者：Ali Khalafi-Nezhad、Somayeh Mohammadi

  DOI：10.1021/co400080z

  日期：2013.9.9

  Magnetic, supported, acidic ionic liquid was synthesized and identified as an efficient catalyst for the one-pot synthesis of novel spirooxindole derivatives at mild conditions and in good yields. Three component reaction of wide variety of substituted isatins, 1,3-dimethyl-2-amino uracil, and barbituric acid, thiobarbituric acid, and dimedon as 1,3-dicarbonyl compounds gives the target compounds.

  合成了磁性负载型酸性离子液体，并确定其为在温和条件下以高收率一锅合成新型螺氧杂吲哚衍生物的有效催化剂。各种取代的靛红，1，3-二甲基-2-氨基尿嘧啶和巴比妥酸，硫代巴比妥酸和二聚体作为1，3-二羰基化合物的三组分反应得到目标化合物。该方法的关键特征是操作简便，成本低，产率高，环境友好，广泛的适用性和可重复使用性以及使用外磁体容易回收催化剂。
• Sulfanilic acid functionalized mesoporous SBA-15: A water-tolerant solid acid catalyst for the synthesis of uracil fused spirooxindoles as antioxidant agents
  作者：ROBABEH BAHARFAR、RAZIEH AZIMI

  DOI：10.1007/s12039-015-0910-2

  日期：2015.8

  Incorporating sulfanilic acid as a hydrophobic Brønsted acid inside the nanospaces of SBA-15 led to a water-tolerant solid acid catalyst, SBA-15-PhSO3H, which showed excellent catalytic performance in synthesis of uracil-fused spirooxindoles in aqueous ethanol. The synthesized compounds were evaluated for their antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay. Green

  在SBA-15的纳米空间内引入磺胺酸作为疏水性布朗斯台德酸，产生了耐水的固体酸催化剂SBA-15-PhSO 3 H，在乙醇水溶液中尿嘧啶融合的螺氧并吲哚合成中显示出优异的催化性能。通过1，1-二苯基-2-吡啶并肼基（DPPH）自由基清除试验评估合成的化合物的抗氧化活性。 描述了使用磺胺酸官能化的SBA-15作为可重复使用的多相酸催化剂的绿色合成尿嘧啶融合的螺硫醇，及其合成化合物的抗氧化活性。
• Dual role of the polymer supported catalyst PEG-OSO3H in aqueous reaction medium: synthesis of highly substituted structurally diversified coumarin and uracil fused spirooxindoles
  作者：Sanjay Paul、Asish R. Das

  DOI：10.1016/j.tetlet.2012.12.079

  日期：2013.2

  coumarin fused spirooxindole derivatives, making this strategy very useful in diversity-oriented synthesis (DOS). This synthesis was established to follow the group-assistant-purification chemistry process (GAP) avoiding traditional chromatography, whereupon recrystallization purifications appear to be a very good alternative to the traditional classical methods. The aqueous reaction medium, dual role

  已经开发了用于合成尿嘧啶和香豆素稠合的螺氧杂吲哚衍生物的文库的高度收敛，有效和实用的异环化方案。涉及PEG-OSO 3的反应H介导的1,3-二酮化合物（环己烷-1,3-二酮，茚满-1,3-二酮，二甲酮和1,3-二甲基巴比妥酸）的一锅三组分多米诺偶联，6-氨基尿嘧啶/ 4 -氨基香豆素和isatin / 5-bromoisatin导致高度取代的尿嘧啶和香豆素稠合的螺氧杂吲哚衍生物，使得该策略在面向多样性的合成（DOS）中非常有用。建立该合成方法是遵循避免化学色谱的组助纯化化学过程（GAP），因此重结晶纯化似乎是传统经典方法的很好替代方法。水性反应介质，聚合物负载催化剂PEG-OSO 3的双重作用水性介质中的H，容易回收的催化剂以及高收率使该方案具有吸引力，可持续性和经济性。
• An Efficient One-pot Synthesis of Novel Spiro Cyclic 2-Oxindole Derivatives of Pyrimido[4,5-<i>b</i>]Quinoline, Pyrido[2,3-<i>d</i>:6,5-<i>d′</i>]Dipyrimidine and Indeno[2′,1′:5,6]Pyrido [2,3-<i>d</i>]Pyrimidine in Water
  作者：Amr Mohamed Abdelmoniem、Huwaida M. E. Hassaneen、Ismail Abdelshafy Abdelhamid

  DOI：10.1002/jhet.2480

  日期：2016.11

  A novel and facile one‐pot synthesis of spiro cyclic 2‐oxindole derivatives of pyrimido[4,5‐b]quinoline‐4,6‐dione, pyrido[2,3‐d:6,5‐d′]dipyrimidine‐2,4,6‐trione, and indeno[2′,1′:5,6]pyrido [2,3‐d]pyrimidine employing 6‐aminothiouracil (or 6‐aminouracil), isatin, and cyclic 1,3‐diketone (e.g. 1,3‐indanedione, dimedone, or barbituric acid) has been developed.

  嘧啶[4,5 - b ]喹啉-4,6-二酮，吡啶并[2,3- d：6,5 - d' ] dipyrimidine -2的螺环2-氧吲哚衍生物的新颖且简便的一锅合成，4,6-三酮和茚并[2'，1'：5,6]吡啶[2,3- d ]嘧啶，使用6-氨基硫氧嘧啶（或6-氨基尿嘧啶），靛红和环状1,3-二酮（例如1,3-茚满二酮，二甲酮或巴比妥酸。
• A new silica-supported organocatalyst based on L-proline: An efficient heterogeneous catalyst for one-pot synthesis of spiroindolones in water
  作者：Ali Khalafi-Nezhad、Elham Shaikhi Shahidzadeh、Samira Sarikhani、Farhad Panahi

  DOI：10.1016/j.molcata.2013.07.009

  日期：2013.11

  A simple and practical synthetic strategy for the synthesis of a novel silica-supported organocatalyst system based on L-proline (SSLP) has been developed. First, silica was treated with trimethoxy(vinyl)silane to produced a vinyl-silica (VS) substrate. Then, VS was oxidized using H2O2 to generate the silica-oxiran (SO) material. Finally, ring-opening of oxiranes in SO substrate with L-proline was resulted the production of SSLP catalyst. The catalytic performance of SSLP was evaluated in the three-component synthesis of spirooxindole derivatives via the condensation reaction of isatins and dicarbonyl compounds in water. All reactions were completed in short times and all products were obtained in good to excellent yields. Besides, SSLP could be recovered for 8 times without any additional treatments. (C) 2013 Elsevier B.V. All rights reserved.