5-amino-8-nitro-2'-oxo-2,3-dihydro-1H-spiro[imidazo[1,2-a]pyridine-7,3'-indoline]-6-carbonitrile | 1263201-48-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 5-amino-8-nitro-2'-oxo-2,3-dihydro-1H-spiro[imidazo[1,2-a]pyridine-7,3'-indoline]-6-carbonitrile
• 英文别名: 5'-amino-8'-nitro-2-oxospiro[1H-indole-3,7'-2,3-dihydro-1H-imidazo[1,2-a]pyridine]-6'-carbonitrile
• CAS: 1263201-48-4
• 化学式: C₁₅H₁₂N₆O₃
• 分子量: 324.299
• InChiKey: QZCSMOSTPUEJNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  靛红 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 5-amino-8-nitro-2'-oxo-2,3-dihydro-1H-spiro[imidazo[1,2-a]pyridine-7,3'-indoline]-6-carbonitrile
  参考文献：
  名称：

  Design, synthesis and insecticidal activity of spiro heterocycle containing neonicotinoid analogs

  摘要：

  Spiro heterocycles frequently occur in bioactive molecules. In the pursuit of neonicotinoids with Spiro heterocycles, three types of novel neonicotinoids with spirobenzofuranone, spirooxindole or spiroacenaphythylenone framework were designed and synthesized. Insecticidal evaluation showed that some of spirobenzofuranone containing neonicotinoids exhibited moderate activity against cowpea aphid, armyworm or brown planthopper. (C) 2013 Xu-Sheng Shao and Zhong Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.12.004

文献信息

• Application of PEG-400 as a green biodegradable polymeric medium for the catalyst-free synthesis of spiro-dihydropyridines and their use as acetyl and butyrylcholinesterase inhibitors
  作者：Ammar Maryamabadi、Alireza Hasaninejad、Najmeh Nowrouzi、Gholamhossein Mohebbi、Behvar Asghari

  DOI：10.1016/j.bmc.2016.02.019

  日期：2016.3

  A simple, efficient and green approach for the synthesis of spiro-dihydropyridines derivatives by one-pot multi-component reaction of isatin or acenaphthoquinone derivatives (1 equiv) with malononitrile (1 equiv) and N,N′-substituted-2-nitroethene-1,1-diamines (1 equiv) in PEG-400 under catalyst-free conditions is described. This method provides several advantages such as environmental friendliness

  一种简单，有效且绿色的方法，是通过一锅多组分的靛红或萘醌衍生物（1当量）与丙二腈（1当量）和N，N合成螺二氢吡啶衍生物描述了在无催化剂条件下在PEG-400中的'-取代的-2-硝基乙烯-1,1-二胺（1当量）。该方法具有许多优点，例如环境友好，反应时间短和生物重要化合物合成的简单后处理程序。在体外和计算机上研究了合成的化合物抑制乙酰基和丁酰胆碱酯酶的能力。所有化合物均显示出对乙酰和丁酰胆碱酯酶的中等至高水平活性。体外和计算机模拟研究之间具有良好的相关性。
• Efficient One-Pot Synthesis of Spirooxindole Derivatives Containing 1,4-Dihydropyridine-Fused-1,3-Diazaheterocycle Fragments via Four-Component Reaction
  作者：Abdolali Alizadeh、Tahereh Firuzyar、Azadeh Mikaeili

  DOI：10.1055/s-0030-1258249

  日期：2010.11

  An efficient, one-pot synthetic protocol toward spirooxindole derivatives containing 1,4-dihydropyridine-fused 1,3-diazaheterocycle fragments, a class of biologically active compounds starting from 1,1-bis(methylthio)-2-nitroethylene, 1,n-diamine, isatin, or its derivatives, and malononitrile is described. The reaction proceeds in ethanol in the presence of 10 mol% of piperidine as a basic catalyst

  一种高效的一锅合成方法，针对含有1,4-二氢吡啶稠合的1,3-二氮杂杂环片段（从1,1-双（甲硫基）-2-硝基乙烯1，n开始的一类生物活性化合物）的螺并吲哚衍生物描述了-二胺，靛红或其衍生物和丙二腈。反应在乙醇中，在作为碱性催化剂的10摩尔％哌啶的存在下，在回流条件下进行，以74-85％的产率产生标题化合物。 螺虫醇-1,4-二氢吡啶-丙二腈-1，n-二胺-1,1-双（甲硫基）-2-硝基乙烯-多组分反应
• Design, synthesis and insecticidal activity of spiro heterocycle containing neonicotinoid analogs
  作者：Nan-Yang Chen、Li-Ping Ren、Min-Ming Zou、Zhi-Ping Xu、Xu-Sheng Shao、Xiao-Yong Xu、Zhong Li

  DOI：10.1016/j.cclet.2013.12.004

  日期：2014.2

  Spiro heterocycles frequently occur in bioactive molecules. In the pursuit of neonicotinoids with Spiro heterocycles, three types of novel neonicotinoids with spirobenzofuranone, spirooxindole or spiroacenaphythylenone framework were designed and synthesized. Insecticidal evaluation showed that some of spirobenzofuranone containing neonicotinoids exhibited moderate activity against cowpea aphid, armyworm or brown planthopper. (C) 2013 Xu-Sheng Shao and Zhong Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.