3-(2-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine | 2827-95-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine
• 英文别名: 3-(2-Methoxyphenyl)-1,2,4-triazolo[4,3-a]pyridine
• CAS: 2827-95-4
• 化学式: C₁₃H₁₁N₃O
• 分子量: 225.25
• InChiKey: JSQHVSUTHHLLAC-UHFFFAOYSA-N

物化性质

• 熔点：
  74 °C
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-methoxy-N'-pyridin-2-ylbenzohydrazide 在 溶剂黄146 作用下， 反应 0.5h， 以391 mg的产率得到3-(2-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine
  参考文献：
  名称：

  钯催化的肼类化合物的化学选择性单芳基化反应用于合成[1,2,4] Triazolo [4,3- a ]吡啶

  摘要：

  合成[1,2,4]三唑并[4,3- a ]吡啶的一种有效而方便的方法，是通过合成20个在3位带有取代基的类似物来举例说明的。该方法包括将钯催化的酰肼加成至2-氯吡啶，其在酰肼的末端氮原子上发生化学选择性，然后在微波辐射下于乙酸中脱水。

  DOI：

  10.1021/ol902868q

文献信息

• Palladium-Catalyzed Coupling of Aldehyde-Derived Hydrazones: Practical Synthesis of Triazolopyridines and Related Heterocycles
  作者：Oliver R. Thiel、Michal M. Achmatowicz、Andreas Reichelt、Robert D. Larsen

  DOI：10.1002/anie.201001999

  日期：2010.11.2

  The palladium‐catalyzed intermolecular coupling of aldehyde‐derived hydrazones with chloroazines, followed by oxidative cyclization under mild conditions afforded access to a broad variety of bicyclic heterocyclic scaffolds (see scheme) that have potential for use in drug discovery.

  钯催化的醛衍生的azo酮与氯嗪的分子间偶联，然后在温和的条件下进行氧化环化，可以使用各种各样的双环杂环骨架（参见方案），这些骨架可能会用于药物发现。
• Cu-catalysed direct C–H (hetero)arylation of [1,2,4]triazolo[4,3-a]pyridine to construct deep-blue-emitting luminophores
  作者：Jie Wu、Qiulin You、Jingbo Lan、Qiang Guo、Xiaoyu Li、Ying Xue、Jingsong You

  DOI：10.1039/c5ob00552c

  日期：——

  An efficient protocol for the synthesis of 3-aryl-[1,2,4]triazolo[4,3-a]pyridines has been developed via Cu-catalysed direct C–H (hetero)arylation. The resulting compounds exhibit deep-blue emission with high quantum yields, photostability, and thermal stability.

  已开发出一种高效的协议，通过Cu催化的直接C-H (杂)芳基化合成3-芳基-[1,2,4]三唑并[4,3-a]吡啶。所得化合物表现出深蓝色发射，具有高量子产率、光稳定性和热稳定性。
• Tandem approach for the synthesis of 3-sulfenylimidazo[1,5-a]pyridines from dithioesters
  作者：Ajjahalli. B. Ramesha、Chottanahalli. S. Pavan Kumar、Nagarakere. C. Sandhya、Manikyanahalli. N. Kumara、Kempegowda Mantelingu、Kanchugarakoppal. S. Rangappa

  DOI：10.1039/c6ra03771b

  日期：——

  Iodine-mediated synthesis of 3-sulfenylimidazo[1,5-a]pyridines via C–H functionalization has been achieved using dithioesters, 2-methylaminopyridines and sulfonyl hydrazides. A library of 3-sulfanylimidazopyridines and imidazopyridines with broad functionalities are synthesized under metal-free reaction conditions.

  使用二硫酯，2-甲基氨基吡啶和磺酰肼，可以实现碘经C–H官能团介导的3-亚磺酰基咪唑并[1,5- a ]吡啶的合成。在无金属的反应条件下，合成了具有广泛功能的3-磺酰胺基咪唑并吡啶和咪唑并吡啶的文库。
• One-pot synthesis of N-fused 1,2,4-triazoles and related heterocycles via I2/TBHP-mediated oxidative C N bond formation
  作者：Yachuang Wu、Yifeng Yang、Yinliang Qi、Shimei Du、Yongsheng Zhang、Liang Ding、Yanfang Zhao

  DOI：10.1016/j.tetlet.2018.10.019

  日期：2018.11

  A metal-free iodine/TBHP-mediated oxidative C-N bond formation for the one-pot synthesis of N-fused 1,2,4-triazoles and related heterocycles via cyclization has been developed. This reaction which is amenable to scale-up affords the corresponding products with good to excellent yields and tolerates a wide range of functional groups. (C) 2018 Elsevier Ltd. All rights reserved.
• An environmentally benign and solvent-free synthesis of 3-aryl[1,2,4]triazolo[4,3-a]pyridines and 1-aryl-5-methyl[1,2,4]triazolo[4,3-a]quinolines using phenyliodine bis(trifluoroacetate) or iodobenzene diacetate
  作者：P. Kumar

  DOI：10.1007/s10593-012-0899-0

  日期：2012.1

  A simple, solvent-free and effective method for oxidative cyclization of 2-pyridyl-and 2-quinolyl-hydrazones with phenyliodine bis(trifluoroacetate) and iodobenzene diacetate to the corresponding 3-aryl[1,2,4]triazolo[4,3-a]pyridines and 1-aryl[1,2,4]triazolo[4,3-a]quinolines is described. All reactions were characterized by short reaction times and high yields at room temperature. All reactions were carried out by just grinding the reaction components.