N-tert-butyl-2-(3-nitrophenyl)imidazo[1,2-a]pyridin-3-amine | 1171753-50-6

• 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-(3-nitrophenyl)imidazo[1,2-a]pyridin-3-amine
• CAS: 1171753-50-6
• 化学式: C₁₇H₁₈N₄O₂
• 分子量: 310.356
• InChiKey: IGWJCKUSTGVTAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 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：
  75.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-tert-butyl-2-(3-nitrophenyl)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 N-(tert-butyl)-2-(thiophen-2-yl)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：

  2-(3-bromophenyl)-N-(tert-butyl)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 N-tert-butyl-2-(3-nitrophenyl)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

• A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating
  作者：Gabriela Santos、Nicolas Anjos、Miguel Gibeli、Guilherme Silva、Pâmela Fernandes、Everton Fiorentino、Luiz Longo Jr.

  DOI：10.21577/0103-5053.20200028

  日期：——

  Over the last twenty years. the Groebke-Blackburn-Bienayme (GBB) reaction has been emerged as a powerful tool to access different nitrogen-based heterocycles as privileged scaffolds in medicinal chemistry. This multicomponent reaction is usually catalyzed by ordinary Bronsted or Lewis acid catalysts. Herein, we present a comparative study on the catalytic efficiencies of different rare earth triflates in GBB reactions under microwave heating, involving 2-aminopyridine or 2-aminothiazole, as aminoazole component, and different aldehydes and aliphatic isocyanides. The use of gadolinium(III) triflate as cheaper alternative catalyst for the most commonly used scandium(III) titillate was acknowledged for the first time, and a library of twenty three imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles could be obtained in good to excellent yields.
• 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.
• 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.