4-phenyl-2-(o-tolyl)-2H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-phenyl-2-(o-tolyl)-2H-1,2,3-triazole
• 英文别名: 4-phenyl-2-o-tolyl-2H-[1,2,3]triazole；2-(2-Methylphenyl)-4-phenyltriazole
• 化学式: C₁₅H₁₃N₃
• 分子量: 235.288
• InChiKey: PQSQCCCCHIXTPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙炔 在 叠氮基三甲基硅烷 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 4-phenyl-2-(o-tolyl)-2H-1,2,3-triazole
  参考文献：
  名称：

  Catalyst-Free Regioselective N² Arylation of 1,2,3-Triazoles Using Diaryl Iodonium Salts

  摘要：

  The widespread application of 1,2,3-triazoles in pharmaceuticals has resulted in substantial interest toward developing efficient postmodification methods. Whereas there are many postmodification methods available to obtain N-1-substituted 1,2,3-triazoles, developing a selective and convenient protocol to synthesize N-2-aryl-1,2,3-triazoles has been challenging. We report a catalyst-free and regioselective method to access N-2-aryl-1,2,3-triazoles in good to excellent yields (66-97%). This scalable postmodification protocol is effective for a wide range of substrates.

  DOI：

  10.1021/acs.orglett.9b02140

文献信息

• Simple and Efficient One‐Pot Synthesis of 2,4‐Diaryl‐1,2,3‐triazoles
  作者：Wen‐Jie Tang、Yong‐Zhou Hu

  DOI：10.1080/00397910600781216

  日期：2006.8.1

  Abstract A general and efficient method for the preparation of 2,4‐diaryl‐1,2,3‐triazoles from α‐hydroxyacetophenones and phenylhydrazines is reported. The essential characteristics of this method include mild reaction conditions, a straightforward workup procedure, and comparatively higher yields.

  摘要 报道了一种从 α-羟基苯乙酮和苯肼制备 2,4-二芳基-1,2,3-三唑的通用且有效的方法。这种方法的基本特征包括温和的反应条件、简单的后处理程序和相对较高的收率。
• A Novel and Efficient Strategy for the Preparation of 2,4-Disubstituted-1,2,3-triazoles
  作者：Yun Luo、Yongzhou Hu

  DOI：10.1081/scc-120024731

  日期：2003.10

  Abstract We have developed a novel and efficient method for the preparation of 2,4-disubstituted-1,2,3-triazoles. These compounds 3a–3p were synthesized in good yield by refluxing α-aminoacetophenones and hydrazines in glacial acetic acid. The reaction proceeds under mild conditions and is compatible with various functional groups.

  摘要 我们开发了一种新型有效的制备 2,4-二取代-1,2,3-三唑的方法。这些化合物 3a-3p 通过在冰醋酸中回流 α-氨基苯乙酮和肼以良好的收率合成。该反应在温和的条件下进行，并与各种官能团相容。
• Another Way to the Synthesis of 1,2,3-Triazoles
  作者：Beihua Xu、Yongzhou Hu

  DOI：10.1002/jhet.1095

  日期：2013.7

  The reactions of α‐bromoacetophenones with methylhydrazine in refluxing acetic acid generated 2‐methyl‐4‐aryl‐2H‐[1,2,3]triazoles in good yields. The method was developed by the reactions of α‐bromoacetophenones with phenylhydrazines in the presence of cupric ion, leading to 2,4‐diary‐2H‐[1,2,3]triazoles. The structures were established on the basis of corresponding IR, 1H NMR, and elemental analysis data.
• Catalyst-Free Regioselective N² Arylation of 1,2,3-Triazoles Using Diaryl Iodonium Salts
  作者：Sahar Roshandel、Maiko J. Lunn、Golam Rasul、Daniel Sylvinson Muthiah Ravinson、Suresh C. Suri、G. K. Surya Prakash

  DOI：10.1021/acs.orglett.9b02140

  日期：2019.8.16

  The widespread application of 1,2,3-triazoles in pharmaceuticals has resulted in substantial interest toward developing efficient postmodification methods. Whereas there are many postmodification methods available to obtain N-1-substituted 1,2,3-triazoles, developing a selective and convenient protocol to synthesize N-2-aryl-1,2,3-triazoles has been challenging. We report a catalyst-free and regioselective method to access N-2-aryl-1,2,3-triazoles in good to excellent yields (66-97%). This scalable postmodification protocol is effective for a wide range of substrates.