2-(1H-1,2,3-triazol-1-yl)-1H-indole | 1225068-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(1H-1,2,3-triazol-1-yl)-1H-indole
• 英文别名: 2-[1,2,3]triazol-1-yl-1H-indole；2-(triazol-1-yl)-1H-indole
• CAS: 1225068-03-0
• 化学式: C₁₀H₈N₄
• 分子量: 184.2
• InChiKey: FNURWLTVFJCXJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1H-1,2,3-三氮唑 、 吲哚 在 叔丁基过氧化氢 、 碘 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以53%的产率得到2-(1H-1,2,3-triazol-1-yl)-1H-indole
  参考文献：
  名称：

  Iodine-Catalyzed Oxidative Cross-Coupling of Indoles and Azoles: Regioselective Synthesis of N-Linked 2-(Azol-1-yl)indole Derivatives

  摘要：

  A highly efficient iodine-catalyzed regioselective oxidative cross-coupling of an indole C-H bond and azole N-H bond is described. This metal-free reaction can be easily carried out at room temperature under mild and environmentally friendly conditions and provides a series of N-linked 2-(azol-1-yl)indole derivatives in moderate to excellence yields.

  DOI：

  10.1021/jo502933e

文献信息

• Highly Regioselective C–N Bond Formation through C–H Azolation of Indoles Promoted by Iodine in Aqueous Media
  作者：Wen-Bin Wu、Jing-Mei Huang

  DOI：10.1021/ol302609m

  日期：2012.12.7

  An efficient and metal-free method for the direct C-N coupling of indoles with azoles to produce 2-(azol-1-yl)indoles in aqueous solution has been developed. This reaction proceeded highly regioselectively to provide a variety of indole derivatives with good to excellent yields.
• Metal-Free Coupling of Azoles with 2- and 3-Haloindoles Providing Access to Novel 2- or 3-(Azol-1-yl)indole Derivatives
  作者：Martin Poirier、Sébastien Goudreau、Jason Poulin、Jolaine Savoie、Pierre L. Beaulieu

  DOI：10.1021/ol100685p

  日期：2010.5.21

  Thermal or microwave-mediated heating of 2- or 3-haloindoles with azoles (pK(a) < 8) provides a straightforward, metal-free, and environmentally friendly access to novel 2-(azol-1-yl)indoles. Furthermore, previously unknown 2,3-bis(azolyl-1-yl)indoles can be prepared from 2,3-dihaloindoles by sequential reaction with two distinct azoles. This operationally simple acid-catalyzed process delivers novel indole derivatives in fair to excellent yields and expands the chemical diversity of substitutions that can be introduced on this medicinally important scaffold.
• Iodine-Catalyzed Oxidative Cross-Coupling of Indoles and Azoles: Regioselective Synthesis of <i>N</i>-Linked 2-(Azol-1-yl)indole Derivatives
  作者：Danupat Beukeaw、Kwanchanok Udomsasporn、Sirilata Yotphan

  DOI：10.1021/jo502933e

  日期：2015.4.3

  A highly efficient iodine-catalyzed regioselective oxidative cross-coupling of an indole C-H bond and azole N-H bond is described. This metal-free reaction can be easily carried out at room temperature under mild and environmentally friendly conditions and provides a series of N-linked 2-(azol-1-yl)indole derivatives in moderate to excellence yields.