3-(4-nitrophenyl)-[1,2,4]triazolo[4,3-a]pyridine | 2746-39-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-nitrophenyl)-[1,2,4]triazolo[4,3-a]pyridine
• 英文别名: 3-(4-nitrophenyl)-1,2,4-triazolo[4,3-a]pyridine；3-(4-nitro-phenyl)-[1,2,4]triazolo[4,3-a]pyridine；3-<4-Nitro-phenyl>-s-triazolo<4,3-a>pyridin；Pyrido<2,1-c>-3-<4-nitro-phenyl>-s-triazol；3-(4-Nitrophenyl)[1,2,4]triazolo[4,3-a]pyridine
• CAS: 2746-39-6
• 化学式: C₁₂H₈N₄O₂
• 分子量: 240.221
• InChiKey: WFJDABYYNJGGRK-UHFFFAOYSA-N

物化性质

• 熔点：
  285 °C
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-肼吡啶 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 3-(4-nitrophenyl)-[1,2,4]triazolo[4,3-a]pyridine
  参考文献：
  名称：

  [双(三氟乙酰氧基)碘]苯催化杂环腙氧化分子内环化高效合成3-取代1,2,4-三唑并[4,3-a]吡啶

  摘要：

  摘要 通过杂环腙与[双(三氟乙酰氧基)碘]苯的分子内氧化环化反应制备了一系列1,2,4-三唑并吡啶。通过 1,2,4-三唑并 [4,3-a] 吡啶的合成证实了这种简单转化的普遍适用性。该协议的优点是催化剂的无毒和较短的反应时间，以获得良好的制备收率。

  DOI：

  10.1080/00397911003707162

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。
• Synthesis of 1,2,4-Triazolo[4,3-<i>a</i> ]pyridines and Related Heterocycles by Sequential Condensation and Iodine-Mediated Oxidative Cyclization
  作者：Ertong Li、Zhiyuan Hu、Lina Song、Wenquan Yu、Junbiao Chang

  DOI：10.1002/chem.201601744

  日期：2016.7.25

  A facile and efficient approach to access 1,2,4‐triazolo[4,3‐a]pyridines and related heterocycles has been accomplished through condensation of readily available aryl hydrazines with corresponding aldehydes followed by iodine‐mediated oxidative cyclization. This transition‐metal‐free synthetic process is broadly applicable to a variety of aromatic, aliphatic, and α,β‐unsaturated aldehydes, and can

  通过容易获得的芳基肼与相应的醛缩合，然后由碘介导的氧化环化反应，可以轻松而有效地获得1,2,4-三唑并[4,3- a ]吡啶和相关杂环。这种无过渡金属的合成方法广泛适用于各种芳香族，脂肪族和α，β-不饱和醛类，并且可以以克为单位方便地进行。
• RuCl3/Oxone: An efficient combination for the synthesis of 3-aryl-[1,2,4]triazolo[4,3-a]pyridines from 2-(2-arylidenehydrazinol)pyridines
  作者：Tallapally Swamy、Padma Raviteja、Goskula Srikanth、Basi V. Subba Reddy、Vadde Ravinder

  DOI：10.1016/j.tetlet.2016.10.110

  日期：2016.12

  An efficient and convenient method for the synthesis of 3-aryl[1,2,4]triazolo[4,3-a]pyridines has been developed involving RuCl3/Oxone oxidative cyclization of 2-(2-arylidenehydrazinyl)pyridines, which occurs chemoselectively at the pyridine nitrogen. RuCl3 can be used as an efficient homogeneous catalyst for the synthesis of triazolopyridines through a direct intramolecular cyclization involving CN

  已经开发出一种有效且方便的合成3-芳基[1,2,4]三唑并[4,3- a ]吡啶的方法，该方法涉及RuCl 3 / Oxone对2-（2-亚芳基肼基嗪）吡啶的氧化环化反应。在吡啶氮上有化学选择性。RuCl 3可以用作通过涉及C N键形成的直接分子内环化合成三唑并吡啶的有效均相催化剂。
• 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.
• Palladium-Catalyzed Triazolopyridine Synthesis: Synthesis of 7-Chloro-3-(2-Chlorophenyl)-1,2,4-Triazolo[4,3-a]Pyridine
  作者：Thiel, Oliver R.、Achmatowicz, Michal M.

  DOI：10.15227/orgsyn.090.0287

  日期：——

  Chloramine-T is thermally unstable and heating of chloramines-T beyond the temperature disclosed in this procedure should not be conducted without further safety evaluation. Hydrazine should be handled in a fume hood as it is an animal carcinogen and has been identified it as a potential human carcinogen. In addition, anhydrous hydrazine is potentially explosive, especially in contact with metals, and should only be handled as its hydrate.