N-tert-butyl-2-(4-fluorophenyl)-imidazo[1,2-a]pyridin-3-amine | 552855-95-5

• 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-tert-butyl-2-(4-fluorophenyl)-imidazo[1,2-a]pyridin-3-amine
• 英文别名: N-tert-butyl-2-(4-fluorophenyl)-1H-imidazo[1,2-a]pyridine-3-amine；N-tert-butyl-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-amine
• CAS: 552855-95-5
• 化学式: C₁₇H₁₈FN₃
• 分子量: 283.348
• InChiKey: QAANPAKKIOFEDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-tert-butyl-2-(4-fluorophenyl)-imidazo[1,2-a]pyridin-3-amine 在 碘苯二乙酸 、 对甲苯磺酸 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 2-(4-bromophenyl)-N-(tert-butyl)imidazo[1,2-a]pyridin-3-amine
  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：

  N-cyclohexyl-2-phenylimidazo[1,2-a]pyridin-3-amine 在 碘苯二乙酸 、 对甲苯磺酸 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 N-tert-butyl-2-(4-fluorophenyl)-imidazo[1,2-a]pyridin-3-amine
  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

文献信息

• Efficient Synthesis of 3-Aminoimidazo[1,2-a] Pyridines Using Silica-Supported Perchloric Acid (HClO4-SiO2) as a Novel Heterogenous Catalyst
  作者：Azizollah Habibi、Zahra Tarameshloo、Shahnaz Rostamizadeh、Ali M. Amani

  DOI：10.2174/157017812800167439

  日期：2012.3.1

  An efficient and green protocol for synthesis of 3-aminoimidazo[1,2-a] pyridine derivatives through a three-component reaction of aldehyde, 2-amino pyridine and isocyanide in the presence of silica-supported perchloric acid (HClO4-SiO2) is described in this paper. The solid catalyst could be recycled and reused.

  在二氧化硅负载的高氯酸 (HClO4-SiO2) 存在下，通过醛、2-氨基吡啶和异氰化物的三组分反应合成 3-氨基咪唑并[1,2-a] 吡啶衍生物的高效绿色方案是在本文中描述。固体催化剂可回收再利用。
• 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。
• 一种α-羰基酰胺衍生物的制备方法
  申请人：贵州大学

  公开号：CN109096139B

  公开（公告）日：2021-03-02

  本发明公开了一种α‑羰基酰胺衍生物的制备方法，即：采用吡啶并咪唑胺类化合物与水在氧化剂作用下发生开环反应，同时插入氧原子，制备得到α‑羰基酰胺衍生物的方法。本方法操作简单，底物普适性广，反应过程中无金属催化，不需要无水无氧的条件，其结构中“O”原子来源于水，副产物可作为制备本发明所采用吡啶并咪唑胺类的原料，从而实现其再循环利用。本方法还具有收率高、可用于大量制备α‑羰基酰胺衍生物和制备部分现有方法中较难制备α‑羰基酰胺衍生物等优点。
• 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.