1,3-dimethylspiro[indeno[2',1':5,6]pyrido[2,3-d]pyrimidine-5,3'-indoline]-2,2',4,6(1H,3H,11H)-tetraone | 1258795-64-0

• 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-dimethylspiro[indeno[2',1':5,6]pyrido[2,3-d]pyrimidine-5,3'-indoline]-2,2',4,6(1H,3H,11H)-tetraone
• 英文别名: 1,3-dimethyl-1H-spiro[indeno[1,2-b]pyrido[2,3-d]pyrimidine-5,3'-indoline]-2,2',4,6(3'H,10'H)-tetraone；spiro[1H-indeno[1,2-b]pyrido[2,3-d]pyrimidine-5,3'-indoline]-1,3-dimethyl-2,2',4,6(3'H,10'H)-tetraone；5',7'-dimethylspiro[1H-indole-3,2'-5,7,9-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),3(8),11,13,15-pentaene]-2,4',6',17'-tetrone
• CAS: 1258795-64-0
• 化学式: C₂₃H₁₆N₄O₄
• 分子量: 412.404
• InChiKey: LEQGEUIWBKDMKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 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-茚满二酮 、 1,3-二甲基-6-氨基脲嘧啶 、 靛红 以 乙醇 为溶剂， 反应 3.0h， 以89%的产率得到1,3-dimethylspiro[indeno[2',1':5,6]pyrido[2,3-d]pyrimidine-5,3'-indoline]-2,2',4,6(1H,3H,11H)-tetraone
  参考文献：
  名称：

  简单的三组分方法合成螺茚并[ 1,2- b ]吡啶并[2,3 - d ]嘧啶-5,3'-二氢吲哚

  摘要：

  螺啶[1,2- b ]吡啶基[2,3 - d ]嘧啶-5,3'-二氢吲哚和螺ac烯-1,4'-indeno-1,5'-的高效，简单且无催化剂的合成据报道，在回流的乙醇中，通过1，3-茚满二酮，氨基尿嘧啶和靛红或ena-1,2-二酮的三组分反应生成吡啶并[2,3- d ]嘧啶。

  DOI：

  10.1021/co1000053

文献信息

• Sonosynthesis of spiroindolines using functionalized SBA-15
  作者：Seyyed Mohammad Ebrahimi、Ali Kareem Abbas、Hossein Shahbazi-Alavi、Javad Safaei-Ghomi、Atefeh Bakhtiari、Raheleh Teymuri

  DOI：10.1007/s11164-021-04506-7

  日期：2021.10

  Functionalized SBA-15 (immobilization of Pd on the modified SBA-15) has been used as an efficient catalyst for the preparation of spiroindolines by multi-component reactions of isatins, cyclic-1,3-diketones, and 6-amino-1,3-dimethyluracil under ultrasonic irradiation in water. The catalyst has been characterized by X-ray diffraction spectroscopy (XRD), field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), energy-dispersive X-ray spectroscopy (EDX), X-ray photoelectron spectroscopy (XPS), Fourier transform infrared spectroscopy (FT-IR), N2 adsorption analysis, temperature-programmed desorption (TPD), and thermogravimetric analysis (TGA). The advantages of this method include the reusability of the catalyst, low catalyst loading, excellent yields in short reaction times and easy separation of products, and use of ultrasonic irradiation as a valuable and powerful technology.

  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。
• Tetramethylguanidinium triflate: An efficient catalyst solvent for the convergent synthesis of fused spiro[1,4-dihydropyridine-oxindole] compounds
  作者：Kurosh Rad-Moghadam、Leila Youseftabar-Miri

  DOI：10.1016/j.jfluchem.2011.11.007

  日期：2012.3

  Synthesis of spiro[1H-indeno[1,2-b]benzoquinolin-13,3′-indoline]-7,13-dihydro-12,2′-dione derivatives was achieved expediently through three-component reactions between 2H-indene-1,3-dione, 1- or 2-naphthalenamine, and isatin derivatives under catalysis of the ionic liquid N,N,N,N-tetramethylguanidinium triflate. The ionic liquid appeared as a task-specific catalyst solvent being amenable to successive

  螺[1H-茚并[1,2-b]苯并喹啉-13,3'-二氢吲哚] -7,13-二氢-12,2'-二酮衍生物的合成可通过2H-茚-之间的三组分反应方便地实现离子液体N，N，N，N催化下的1,3-二酮，1-或2-萘胺和靛红衍生物-三氟甲磺酸四甲基胍盐。离子液体表现为任务特定的催化剂溶剂，适合连续循环使用，而活性没有明显下降。当使用-1,2-二酮或1H-茚-1,2,3-三酮代替靛红时，以及当使用2-氨基尿嘧啶代替萘胺来提供与结构相关的螺环产物时，该合成方法同样适用。对于反应，提出了一种收敛机制，以解释与所用组分相对应的螺化合物的选择性形成。
• 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。
• One-pot synthesis of indeno-fused spirooxindoles catalyzed by SBA-Oxime-Zn
  作者：Sayed Ghorbani、Mohammad Hashemi

  DOI：10.13005/ojc/31.special-issue1.22

  日期：2015.10.30

  An extremely efficient catalytic protocol for the synthesis of spirooxindole derivatives via a one-pot three component approach in the presence of SBA-Oxime-Zn, as a heterogeneous catalyst using water as a green solvent is reported. The catalyst exhibited excellent catalytic activity, and the proposed methodology is capable of providing the desired products in good yield and short reaction time. After reaction course, the catalyst can be recycled and reused without any apparent loss of activity which makes this process cost effective and hence eco-friendly.