N-2-(2,4,4-trimethylpentan-2-yl) 2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-amine | 859359-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-2-(2,4,4-trimethylpentan-2-yl) 2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-amine
• 英文别名: 2-(4-chlorophenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine
• CAS: 859359-24-3
• 化学式: C₂₁H₂₆ClN₃
• mdl: MFCD19716662
• 分子量: 355.911
• InChiKey: MOLUXYJARYHOCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-2-(2,4,4-trimethylpentan-2-yl) 2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-amine 在 三氟乙酸 作用下， 生成 2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-amine
  参考文献：
  名称：

  聚乙二醇 400 中氯化锆 (IV) 介导的 Ugi 型多组分反应高效、区域选择性、多功能合成 N-稠合 2-和 3-氨基咪唑

  摘要：

  开发了 PEG-400 中氯化锆 (IV) 催化的杂环脒与醛和异氰化物的 Ugi 型多组分反应。该协议提供了快速、环境友好、区域选择性和多功能的医学上重要的 N-融合 2-和 3-氨基咪唑的合成，产量高。明智地探索了催化剂和溶剂的组合，对于该方法的区域选择性和多功能性至关重要。

  DOI：

  10.1055/s-0028-1087915
• 作为产物：
  描述：

  2-氨基吡啶 、 1,1,3,3-四甲基丁基异腈 、 4-氯氯苄 在 potassium carbonate 、 二甲基亚砜 作用下， 反应 6.0h， 以88%的产率得到N-2-(2,4,4-trimethylpentan-2-yl) 2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-amine
  参考文献：
  名称：

  One-pot synthesis of imidazo[1,2-a]pyridines from benzyl halides or benzyl tosylates, 2-aminopyridines and isocyanides

  摘要：

  A one-pot synthesis of imidazo[1,2-a]pyridines is described. Benzyl halides or benzyl tosylates are oxidized to aldehydes under mild Kornblum conditions which then undergo a three-component reaction with various 2-aminopyridines and isocyanides to afford the imidazo[1,2-a]pyridines in excellent yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.002

文献信息

• A Highly Flexible and Efficient Ugi-Type Multicomponent Synthesis of Versatile N-Fused Aminoimidazoles
  作者：Sankar Guchhait、Chetna Madaan、Balmukund Thakkar

  DOI：10.1055/s-0029-1216916

  日期：2009.10

  A microwave-promoted highly flexible and efficient Ugi-type multicomponent reaction of heterocyclic amidines with aldehydes and isocyanides catalyzed by zirconium(IV) chloride was developed. The general protocol offered the very reliable synthesis of a library of medicinally important, widely versatile N-fused aminoimidazoles in excellent yields. Poorly reactive heterocyclic amidines, functionally

  研究了微波促进的高柔性，高效的Ugi型杂环multi与氯化锆（IV）催化的醛和异氰酸酯的多组分反应。该通用方案以极高的收率提供了非常重要的医学上重要的，用途广泛的N融合氨基咪唑库的可靠合成。在较早描述的方法中作为麻烦的反应物遭受的反应性差的杂环am，功能和空间受阻的醛在该方法中被认为是可行的底物。发现ZrCl 4的有效催化以及微波辐照的作用对于获得方案的优异灵活性和效率至关重要。 多组分反应-N-杂环-催化-氯化锆-微波
• Electrostatically Enhanced Sulfuric Acid: A Strong Brønsted Acidic Catalyst for Multi-Component Reactions
  作者：Mohadese Yaghoobi Anzabi、Hossein Yazdani、Ayoob Bazgir

  DOI：10.1007/s10562-019-02776-w

  日期：2019.7

  A new electrostatically enhanced sulfuric acid as a strong Brønsted acidic catalyst has been developed for multi-component reactions. A positively charged center in the catalyst electrostatically activates it for acid-catalyzed multi-component reactions and afforded desired products in short reaction time and near room temperature in EtOH as a green solvent.Graphical Abstract

  一种新的静电增强硫酸作为强 Brønsted 酸性催化剂已被开发用于多组分反应。催化剂中带正电荷的中心通过静电激活它进行酸催化的多组分反应，并在作为绿色溶剂的 EtOH 中在较短的反应时间内和接近室温的时间内提供所需的产物。
• Catalytic activity of aqueous cationic polyurethane dispersions: A novel feature of polyurethanes
  作者：Hamed Daemi、Reza Rezaieyeh Rad、Mehdi Barikani、Mehdi Adib

  DOI：10.1016/j.apcata.2013.08.023

  日期：2013.11

  Polyurethane ionomers are well-known and user-friendly polymers. Here, we introduce their catalytic activity for organic reactions as a novel aspect of these polymers. We selected an isocyanide-based multicomponent reaction for proving the catalytic activity of polyurethane ionomers. Therefore, a convenient and very mild methodology is described for the preparation of 3-aminoimidazo[1,2-a]pyridines via a three component reaction between 2-aminopyridines, aldehydes and isocyanides in the presence of a cationic polyurethane dispersion at low reaction temperatures, in short reaction times and excellent yields. (C) 2013 Elsevier B.V. All rights reserved.
• An Efficient, Regioselective, Versatile Synthesis of N-Fused 2- and 3-Aminoimidazoles via Ugi-Type Multicomponent Reaction Mediated by Zirconium(IV) Chloride in Polyethylene Glycol-400
  作者：Sankar Guchhait、Chetna Madaan

  DOI：10.1055/s-0028-1087915

  日期：2009.3

  An Ugi-type multicomponent reaction of heterocyclic amidines with aldehydes and isocyanides catalyzed by zirconium(IV) chloride in PEG-400 was developed. The protocol offers the rapid, environment friendly, regioselective and versatile synthesis of medicinally important N-fused 2- and 3-aminoimidazoles in good to high yields. The combination of catalyst and solvent, that was judiciously explored, was

  开发了 PEG-400 中氯化锆 (IV) 催化的杂环脒与醛和异氰化物的 Ugi 型多组分反应。该协议提供了快速、环境友好、区域选择性和多功能的医学上重要的 N-融合 2-和 3-氨基咪唑的合成，产量高。明智地探索了催化剂和溶剂的组合，对于该方法的区域选择性和多功能性至关重要。
• One-pot synthesis of imidazo[1,2-a]pyridines from benzyl halides or benzyl tosylates, 2-aminopyridines and isocyanides
  作者：Mehdi Adib、Ehsan Sheikhi、Narjes Rezaei

  DOI：10.1016/j.tetlet.2011.04.002

  日期：2011.6

  A one-pot synthesis of imidazo[1,2-a]pyridines is described. Benzyl halides or benzyl tosylates are oxidized to aldehydes under mild Kornblum conditions which then undergo a three-component reaction with various 2-aminopyridines and isocyanides to afford the imidazo[1,2-a]pyridines in excellent yields. (C) 2011 Elsevier Ltd. All rights reserved.