N-cyclohexyl-6-nitro-2-phenylimidazo[1,2-a]pyridin-3-amine | 1574311-39-9

• 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-6-nitro-2-phenylimidazo[1,2-a]pyridin-3-amine
• 英文别名: N-cyclohexyl-6-nitro-2-phenylimidazo[1,2-a]pyridine-3-amine
• CAS: 1574311-39-9
• 化学式: C₁₉H₂₀N₄O₂
• 分子量: 336.393
• InChiKey: YLQKKWFJMKSVII-UHFFFAOYSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 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-5-硝基吡啶 、 异氰环已烷 、 苯甲醛 在 NaA nanozeolite 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 以68%的产率得到N-cyclohexyl-6-nitro-2-phenylimidazo[1,2-a]pyridin-3-amine
  参考文献：
  名称：

  Synthesized NaA Nanozeolite as a Catalyst for the Preparation of 3-amino imidazo[1,2-a]pyridines under Solvent-Free Conditions

  摘要：

  摘要：本研究探索了一种制备NaA纳米沸石的新方法，作为在无溶剂条件下通过醛，2-氨基吡啶和异腈的三组分反应制备3-氨基咪唑[1,2-a]吡啶的简单高效催化剂。有机模板自由（OTF）的NaA纳米沸石在室温下制备。通过X射线衍射（XRD）、傅里叶变换红外光谱（FT-IR）、场发射扫描电子显微镜（FESEM）、N2吸附等温线和粒径分析（PSA）鉴定了制备的纳米沸石。通过FESEM方法合成的球形NaA纳米沸石的粒径小于100纳米。所创建样品的BET比表面积、总孔体积和平均孔径分别为362 m2g-1、0.44 cm3 g-1和5.9 nm。该方法具有一些优点，如OTF制备NaA纳米沸石、简单的合成方法、短的反应时间和易于通过过滤分离，以及能够多次回收和重复使用催化剂而不降低其效率。

  DOI：

  10.2174/1570178619666211220103759

文献信息

• Visible-light-activated C–C and C–N bond formation in the synthesis of imidazo[1,2-<i>a</i>]pyridines and imidazo[2,1-<i>b</i>]thiazoles under catalyst and solvent-free conditions
  作者：Km Neha Shivhare、Manish K. Jaiswal、Anushree Srivastava、Saurabh K. Tiwari、I. R. Siddiqui

  DOI：10.1039/c8nj03339k

  日期：——

  Synthesis of 3-aminoimidazo-fused heterocycles via the Groebke–Blackburn–Bienaymé reaction using a universally available energy source under catalyst and solvent-free conditions.

  通过Groebke-Blackburn-Bienaymé反应，在无催化剂和溶剂的条件下，利用普遍可获得的能源合成3-氨基咪唑融合杂环化合物。
• A facile protocol for the synthesis of 3-aminoimidazo-fused heterocycles via the Groebke–Blackburn–Bienayme reaction under catalyst-free and solvent-free conditions
  作者：Shinde Vidyacharan、Anand H. Shinde、Bishnupada Satpathi、Duddu S. Sharada

  DOI：10.1039/c3gc42130a

  日期：——

  A one-pot catalyst, solvent, work-up and column free synthesis of 3-aminoimidazo-fused heterocycles by a three-component reaction of a 2-aminoheterocycle, aldehyde, and isocyanide is presented. This efficient and green protocol has the advantages of environmental friendliness, high yields and operational simplicity.

  本文介绍了一种一锅合成3-氨基咪唑融合杂环的催化剂、溶剂、后处理和柱层析免费合成方法，该方法通过2-氨基杂环、醛和异氰酸酯的三组分反应实现。这一高效且绿色的方案具有环境友好、高产率和操作简单的优点。
• A highly efficient synthesis of imidazo-fused polyheterocycles via Groebke–Blackburn–Bienaymè reaction catalyzed by LaCl3·7H2O
  作者：Anand H. Shinde、Malipatel Srilaxmi、Bishnupada Satpathi、Duddu S. Sharada

  DOI：10.1016/j.tetlet.2014.08.126

  日期：2014.10

  A highly efficient and mild protocol for the synthesis of imidazo-fused polyheterocycles via Groebke-Blackburn-Bienayme reaction under the influence of catalytic amount of lanthanum chloride heptahydrate has been described. A wide range of nitrogen-enriched polyheterocycles are synthesized with high yields under neat conditions. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesized NaA Nanozeolite as a Catalyst for the Preparation of 3-amino imidazo[1,2-a]pyridines under Solvent-Free Conditions
  作者：Afshin Sarvary、Sara Azargashb、Seyed Karim Hassaninejad-Darzi

  DOI：10.2174/1570178619666211220103759

  日期：2022.9

  The present study explores a new method for the fabrication of NaA nanozeolite as a simple and efficient catalyst for producing 3-aminoimidazo [1,2-a] pyridines via the 3-component reaction of aldehydes, 2-aminoperidines and isocyanides under solvent-free conditions. The production of the organic template-free (OTF) NaA nanozeolite was performed at room temperature. The prepared nanozeolite was identified by X-ray diffraction (XRD), Fourier Transform infrared spectroscopy (FT-IR), Field Emission Scanning Electronic Microscopy (FESEM), N2 sorption isotherm and Particle Size Analysis (PSA). The particle sizes of synthesized spherical NaA nanozeolite were under 100 nm via the FESEM method. BET surface area, total pore volume, and mean pore diameter of the created sample were attained to be 362 m2g-1, 0.44 cm3 g-1 and 5.9 nm, respectively. The developed method has some advantages, such as OTF production of NaA nanozeolite, a simple synthesis method with short reaction time and easy separation using filtration, and the ability to recycle and reuse the catalyst several times without reducing its efficiency.

  摘要：本研究探索了一种制备NaA纳米沸石的新方法，作为在无溶剂条件下通过醛，2-氨基吡啶和异腈的三组分反应制备3-氨基咪唑[1,2-a]吡啶的简单高效催化剂。有机模板自由（OTF）的NaA纳米沸石在室温下制备。通过X射线衍射（XRD）、傅里叶变换红外光谱（FT-IR）、场发射扫描电子显微镜（FESEM）、N2吸附等温线和粒径分析（PSA）鉴定了制备的纳米沸石。通过FESEM方法合成的球形NaA纳米沸石的粒径小于100纳米。所创建样品的BET比表面积、总孔体积和平均孔径分别为362 m2g-1、0.44 cm3 g-1和5.9 nm。该方法具有一些优点，如OTF制备NaA纳米沸石、简单的合成方法、短的反应时间和易于通过过滤分离，以及能够多次回收和重复使用催化剂而不降低其效率。