N-cyclohexyl-2-(2-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine | 855140-42-0

• 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-2-(2-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine
• CAS: 855140-42-0
• 化学式: C₂₀H₂₃N₃O
• 分子量: 321.422
• InChiKey: GXJFRHIBYSBIGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-cyclohexyl-2-(2-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine 在 碘苯二乙酸 、 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以91%的产率得到<2-Methoxy-phenyl>-glyoxylsaeure-cyclohexylamid
  参考文献：
  名称：

  Diverse Oxidative C(sp²)–N Bond Cleavages of Aromatic Fused Imidazoles for Synthesis of α-Ketoamides and N-(pyridin-2-yl)arylamides

  摘要：

  An efficient and chemoselective C(sp(2))-N bond cleavage of aromatic imidazo[1,2-a]pyridine molecules is developed. A broad scope of amide compounds such as alpha-ketoamides and N-(pyridin-2-yl)arylamides are afforded as the final products in up to quantitative yields. Diverse C-N bond cleavages are controlled by the oxidative species used in this transformation, with various amide products afforded in a chemoselective fashion. A preliminary study indicated that some alpha-ketoamides exhibit anti-Tobacco Mosaic Virus activity for potential use in plant protection.

  DOI：

  10.1021/acs.joc.9b00208
• 作为产物：
  描述：

  2-氨基吡啶 、 异氰环已烷 、 邻甲氧基苯甲醛 以 neat (no solvent) 为溶剂， 反应 2.0h， 以86%的产率得到N-cyclohexyl-2-(2-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine
  参考文献：
  名称：

  A facile protocol for the synthesis of 3-aminoimidazo-fused heterocycles via the Groebke–Blackburn–Bienayme reaction under catalyst-free and solvent-free conditions

  摘要：

  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。

  DOI：

  10.1039/c3gc42130a

文献信息

• 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.
• Diverse Oxidative C(sp²)–N Bond Cleavages of Aromatic Fused Imidazoles for Synthesis of α-Ketoamides and <i>N</i>-(pyridin-2-yl)arylamides
  作者：Fangzhou Xu、Yanyan Wang、Xiwei Xun、Yun Huang、Zhichao Jin、Baoan Song、Jian Wu

  DOI：10.1021/acs.joc.9b00208

  日期：2019.7.5

  An efficient and chemoselective C(sp(2))-N bond cleavage of aromatic imidazo[1,2-a]pyridine molecules is developed. A broad scope of amide compounds such as alpha-ketoamides and N-(pyridin-2-yl)arylamides are afforded as the final products in up to quantitative yields. Diverse C-N bond cleavages are controlled by the oxidative species used in this transformation, with various amide products afforded in a chemoselective fashion. A preliminary study indicated that some alpha-ketoamides exhibit anti-Tobacco Mosaic Virus activity for potential use in plant protection.
• Magnetic mesoporous poly-melamine–formaldehyde: an efficient and recyclable catalyst for straightforward one-pot synthesis of imidazo[1,2-a]pyridines
  作者：Mohammad Heydari、Najmedin Azizi、Zohreh Mirjafari、Mohammad Mahmoudi Hashemi

  DOI：10.1007/s13738-019-01705-3

  日期：2019.11

  synthesized and characterized by FTIR spectroscopy, SEM, XRD spectroscopy and EDS. The magnetically separable Fe3O4@mPMF catalyst had excellent efficiency for the synthesis a wide diversity of imidazo[1,2-a]pyridines by a three-component reaction of a 2-aminopyridine, aldehyde and isocyanide in good-to-excellent yields within a short reaction time, through an environmental friendliness and straightforward

  摘要磁性可分离的介孔聚三聚氰胺-甲醛纳米复合材料（Fe 3 O 4 @mPMF）已通过FTIR光谱，SEM，XRD光谱和EDS进行了表征。磁性可分离的Fe 3 O 4 @mPMF催化剂具有优异的效率，可通过2-氨基吡啶，醛和异氰酸酯的三组分反应以优异的优良性能合成各种咪唑并[1,2-a]吡啶。通过环境友好和简单的程序，可在较短的反应时间内获得产量。当反应完成数次而催化活性没有明显降低时，可以回收并再利用的纳米复合材料易于回收并且也可以重复使用。 图形摘要