8H-[1,2,3]triazolo[5,1-a]isoindole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 8H-[1,2,3]triazolo[5,1-a]isoindole
• 英文别名: 8H-[1,2,3]triazolo[4,3-a]isoindole；5H-triazolo[5,1-a]isoindole
• 化学式: C₉H₇N₃
• mdl: MFCD12923918
• 分子量: 157.175
• InChiKey: AIVXQIMWFLDTCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.111
• 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：

  2-碘苯甲基溴 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 sodium azide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 8H-[1,2,3]triazolo[5,1-a]isoindole
  参考文献：
  名称：

  钯-铜催化炔化合物的异环化：异吲哚啉与三唑的快速合成

  摘要：

  描述了一种方便，通用的方法，该方法通过钯-铜催化从邻碘碘苄基叠氮化物和乙炔合成与三唑稠合的异吲哚啉。

  DOI：

  10.1016/j.tetlet.2005.10.006

文献信息

• Selectfluor-Mediated Synthesis of Isoindoline Fused with Triazoles under Metal-Free Conditions
  作者：Hong-Ping Zhang、Xia Wang

  DOI：10.3184/174751915x14255507995495

  日期：2015.4

  An efficient selectfluor-mediated cyclisation of 2-arylethynyl-benzyl azides at 80 °C in MeCN yielded 12 arylated triazolo-isoindoline derivatives (seven of which are novel). Products bearing either electron-donating or electron-withdrawing groups on the aromatic ring were formed in comparable yields.

  在 80 °C、MeCN 条件下，以选择氟为介质对 2-芳基乙炔基苄基叠氮化物进行高效环化反应，得到了 12 种芳基化的三唑异吲哚啉衍生物（其中 7 种为新型衍生物）。芳香环上带有电子奉献基团或电子吸收基团的产物产量相当。
• Synthesis of Bicyclic Imidazoles via [2 + 3] Cycloaddition between Nitriles and Regioselectively Generated α-Imino Gold Carbene Intermediates
  作者：Yuanjing Xiao、Liming Zhang

  DOI：10.1021/ol302102h

  日期：2012.9.7

  The cyclic alpha-imino gold carbene intermediate B is most likely generated in situ via regioselective nitrene transfer from an azido group to a tethered terminal alkyne in the presence of a gold catalyst and at ambient temperature. This highly electrophilic intermediate can react with a weakly nucleophilic nitrile, which is used as the reaction solvent, to deliver a bicyclic imidazole rapidly in an overall bimolecular [2 + 2 + 1] cycloaddition and in mostly serviceable yield. The competing intramolecular Huisgen reaction, although likely also catalyzed by gold, is minimized by using AuCl3 as the catalyst.
• Facile Synthesis of [1,2,3]-Triazole-Fused Isoindolines, Tetrahydroisoquino­lines, Benzoazepines and Benzoazocines by Palladium-Copper Catalysed Heterocyclisation­
  作者：Chinmay Chowdhury、Kaushik Brahma、Basudeb Achari

  DOI：10.1055/s-0032-1316839

  日期：——

  An elegant method for the synthesis of 1,2,3-triazoles fused with five-, six-, seven- and eight-membered benzoheterocycles, including isoindoline, tetrahydroisoquinoline, benzoazepine and benzoazocine, has been developed via palladium-copper catalysed reactions in one-pot. The broad scope of this reaction was illustrated by effecting bis-heteroannulations, synthesis of uracil derivatives of biological interest, and employment of acetylene gas as an inexpensive substrate. The reactions are experimentally simple and utilise easily accessible substrates of different types.