3-cyclohexylamino-2-(5-methylfuran-2-yl)imidazo[1,2-a]pyridine | 1440522-45-1

• 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: 3-cyclohexylamino-2-(5-methylfuran-2-yl)imidazo[1,2-a]pyridine
• 英文别名: N-cyclohexyl-2-(5-methylfuran-2-yl)imidazo[1,2-a]pyridin-3-amine；N-cyclohexyl-2-(5-methylfuran-2-yl)imidazolo[1,2-a]pyridin-3-amine
• CAS: 1440522-45-1
• 化学式: C₁₈H₂₁N₃O
• 分子量: 295.384
• InChiKey: YYCKJPPOONABKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  42.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-cyclohexylamino-2-(5-methylfuran-2-yl)imidazo[1,2-a]pyridine 在 potassium tert-butylate 、 copper diacetate 作用下， 以 间二甲苯 为溶剂， 反应 10.0h， 以76%的产率得到5-methyl-N-(pyridin-2-yl)furan-2-carboxamide
  参考文献：
  名称：

  一种N-杂环酰胺衍生物的合成方法

  摘要：

  本发明公开了一种N‑杂环酰胺衍生物的合成方法，反应通式如下。即：以咪唑并杂环胺类化合物I为原料，在催化剂的作用下，在碱性条件下于有机溶剂中和80～200℃的条件下与空气或氧气发生反应开环，同时插入氧原子，生成如反应通式所示的N‑杂环酰胺衍生物II。本方法具有操作简单、收率高、底物普适性广等特点。

  公开号：

  CN109053558B
• 作为产物：
  描述：

  2-氨基吡啶 、 5-甲基呋喃醛 、 异氰环已烷 在 氯化铋 作用下， 以 neat (no solvent) 为溶剂， 以92%的产率得到3-cyclohexylamino-2-(5-methylfuran-2-yl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1055/s-0032-1318221

文献信息

• 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.
• A Facile Preparation of Imidazo[1,2-a]pyridin-3-amine Derivatives via a Three-Component Reaction with β-Cyclodextrin–SO3H as Catalyst
  作者：Jian Wu、Fang-Zhou Xu、She-Lei Feng、Wei Xue、Zhen-Zhen Wang

  DOI：10.3987/com-16-13508

  日期：——

  Because heterogeneous catalysts have attracted great interest in organic chemistry, this paper reports facile beta-cyclodextrin-SO3H catalyzed cyclization to form imidazo[1,2-a]pyridin-3-amine derivatives via a three-component reaction. The main advantages of this strategy include short reaction time, practical simplicity, and high yield, and the catalyst can be separated easily by filtration and reused at least four times.
• 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.
• 一种N-杂环酰胺衍生物的合成方法
  申请人：贵州大学

  公开号：CN109053558B

  公开（公告）日：2022-02-18

  本发明公开了一种N‑杂环酰胺衍生物的合成方法，反应通式如下。即：以咪唑并杂环胺类化合物I为原料，在催化剂的作用下，在碱性条件下于有机溶剂中和80～200℃的条件下与空气或氧气发生反应开环，同时插入氧原子，生成如反应通式所示的N‑杂环酰胺衍生物II。本方法具有操作简单、收率高、底物普适性广等特点。