N-cyclohexyl-N-[5-methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridine-3-yl]amine | 1000353-40-1

• 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-cyclohexyl-N-[5-methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridine-3-yl]amine
• 英文别名: N-cyclohexyl-5-methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridin-3-amine
• CAS: 1000353-40-1
• 化学式: C₂₀H₂₂N₄O₂
• 分子量: 350.42
• InChiKey: KHTJCEBCFXRLEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-6-甲基吡啶 、 异氰环已烷 、 对硝基苯甲醛 在 Al⁽³⁺⁾*HO^(1-)*C₈H₅NO₄^(2-)*C₃H₇NO 作用下， 以 neat (no solvent) 为溶剂， 反应 3.33h， 以85%的产率得到N-cyclohexyl-N-[5-methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridine-3-yl]amine
  参考文献：
  名称：

  胺-MIL-53（Al）的金属-有机骨架作为活性和可重复使用的液相反应诱导剂，用于Ugi型反应的多组分缩合

  摘要：

  NH 2 ‐MIL‐53（Al）的金属-有机骨架以及不饱和的铝配合位点在基于Ugi型胺和醛在异氰酸酯上缩合的Groebke-Blackburn-Bienaymé多组分偶联反应中表现出活性，然后环化过程。有趣的是，该反应在无溶剂条件下以高收率进行，其中NH 2 -MIL-53（Al）可以回收并重复使用五个反应周期，总周转数为455。

  DOI：

  10.1002/aoc.3584

文献信息

• RuCl3-catalyzed solvent-free Ugi-type Groebke–Blackburn synthesis of aminoimidazole heterocycles
  作者：Sadegh Rostamnia、Asadollah Hassankhani

  DOI：10.1039/c3ra42752h

  日期：——

  RuCl3 catalyzes the efficient Ugi-type Groebke–Blackburn condensations of aldehydes and 2-amino pyridines with isocyanides under solvent free conditions without any ligand or activator. It is shown that RuCl3 catalyzed aminoimidazole derivatives can be efficiently prepared under mild conditions and high tolerance with typical yields around 94%.

  RuCl3 催化无溶剂条件下在没有任何配体或激活剂的情况下，醛与 2-氨基吡啶及异氰酸酯的高效 Ugi 型 Groebke–Blackburn 缩合反应。研究表明，RuCl3 催化的氨基咪唑衍生物可以在温和的条件下高效制备，并且具有良好的耐受性，典型产率约为 94%。
• Three Novel Sequential Reactions for the Facile Synthesis of a Library of Bisheterocycles Possessing the 3-Aminoimidazo[1,2-a]pyridine Core Cata­lyzed by Bismuth(III) Chloride
  作者：Aziz Shahrisa、Somayeh Esmati

  DOI：10.1055/s-0032-1318221

  日期：——

  Novel, one-pot, two-step, sequential protocols for the synthesis of 1,4-phenylene bisheterocyclic compounds have been developed. Successive sequencing of the Groebke-Blackburn-Bienayme reaction with Ugi-azide, Hantzsch and Biginelli reactions results in rapid and efficient formation of bisheterocyclic compounds. A simple, fast and high yielding method for the synthesis of 3-aminoimidazo[1,2-a]pyridines catalyzed by bismuth(III) chloride under solvent-free conditions is reported. Bismuth(III) chloride is also an efficient catalyst for the Ugi-azide reaction under solvent free conditions.
• Nanomagnetically modified sulfuric acid (γ-Fe2O3@SiO2-OSO3H): an efficient, fast, and reusable green catalyst for the Ugi-like Groebke-Blackburn-Bienaymé three-component reaction under solvent-free conditions
  作者：Sadegh Rostamnia、Kamran Lamei、Mohsen Mohammadquli、Mehdi Sheykhan、Akbar Heydari

  DOI：10.1016/j.tetlet.2012.07.075

  日期：2012.9

  Superparamagnetic nanoparticles of modified sulfuric acid (gamma-Fe2O3@SiO2-OSO3H) represent a straight-forward and green catalyst for the rapid synthesis of aminoimidazopyridine skeletons via the Ugi-like Groebke-Blackburn-Bienayme three-component reaction. The gamma-Fe2O3@SiO2-OSO3H catalyst could be recovered and reused in five reaction cycles, giving a total TON = 453. The products were prepared under solvent-free conditions without any additives. (c) 2012 Elsevier Ltd. All rights reserved.
• Choline chloride/urea as a deep eutectic solvent/organocatalyst promoted three-component synthesis of 3-aminoimidazo-fused heterocycles via Groebke–Blackburn–Bienayme process
  作者：Ahmad Shaabani、Seyyed Emad Hooshmand

  DOI：10.1016/j.tetlet.2015.12.014

  日期：2016.1

  The catalytic activity of urea-, metal- and organic acid-based/choline chloride deep eutectic solvents/organocatalysts was investigated for the synthesis of 3-aminoimidazo-fused heterocycles via a one-pot domino reaction of an aldehyde, an isocyanide and 2-aminoheterocycles. The urea-based/choline chloride system exhibited significant catalytic activity for the reaction and could be reused in four consecutive reactions with no considerable loss in catalytic activity. (C) 2015 Elsevier Ltd. All rights reserved.
• Metal-organic framework of amine-MIL-53(Al) as active and reusable liquid-phase reaction inductor for multicomponent condensation of Ugi-type reactions
  作者：Sadegh Rostamnia、Maryam Jafari

  DOI：10.1002/aoc.3584

  日期：2017.4

  be active in the Groebke–Blackburn–Bienaymé multicomponent coupling reaction based on Ugi‐type amine and aldehyde condensation over isocyanide and then a cyclization process. Interestingly this reaction occurred under solvent‐free conditions with high yield, in which the NH2‐MIL‐53(Al) could be recovered and reused for five reaction cycles, giving a total turnover number of 455.

  NH 2 ‐MIL‐53（Al）的金属-有机骨架以及不饱和的铝配合位点在基于Ugi型胺和醛在异氰酸酯上缩合的Groebke-Blackburn-Bienaymé多组分偶联反应中表现出活性，然后环化过程。有趣的是，该反应在无溶剂条件下以高收率进行，其中NH 2 -MIL-53（Al）可以回收并重复使用五个反应周期，总周转数为455。