3-(4-methoxyphenyl)-8H-[1,2,3]triazolo[5,1-a]isoindole | 1258271-62-3

• 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-methoxyphenyl)-8H-[1,2,3]triazolo[5,1-a]isoindole
• 英文别名: 1-(4-methoxyphenyl)-5H-triazolo[5,1-a]isoindole
• CAS: 1258271-62-3
• 化学式: C₁₆H₁₃N₃O
• 分子量: 263.299
• InChiKey: FWKUZSMQOJMUKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-iodobenzyl methanesulfonate 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 4.5h， 生成 3-(4-methoxyphenyl)-8H-[1,2,3]triazolo[5,1-a]isoindole
  参考文献：
  名称：

  Facile Synthesis of [1,2,3]-Triazole-Fused Isoindolines, Tetrahydroisoquino­lines, Benzoazepines and Benzoazocines by Palladium-Copper Catalysed Heterocyclisation­

  摘要：

  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.

  DOI：

  10.1055/s-0032-1316839

文献信息

• Bifunctional Metal Organic Framework Catalysts for Multistep Reactions: MOF-Cu(BTC)-[Pd] Catalyst for One-Pot Heteroannulation of Acetylenic Compounds
  作者：Avelina Arnanz、Mercedes Pintado-Sierra、Avelino Corma、Marta Iglesias、Félix Sánchez

  DOI：10.1002/adsc.201100503

  日期：2012.5.7

  A bifunctional metal organic framework catalyst containing palladium and copper(II) benzene‐1,3,5‐tricarboxylate – MOF‐Cu(BTC)‐[Pd] – has been prepared. This catalyst enables the performance of the tandem Sonogashira/click reaction starting from 2‐iodobenzylbromide, sodium azide and alkynes to produce 8H‐[1,2,3]triazolo[5,1‐a]isoindoles with good yields under mild reaction conditions.

  制备了一种含钯和铜（II）苯-1,3,5-三羧酸盐（MOF-Cu（BTC）-[Pd]）的双功能金属有机骨架催化剂。该催化剂能够从2-碘代苄基溴化物，叠氮化钠和炔烃开始进行串联Sonogashira / click反应，以在温和的反应条件下以良好的收率生产8 H- [1,2,3]三唑[5,1- a ]异吲哚。
• Palladium and copper-supported on charcoal: A heterogeneous multi-task catalyst for sequential Sonogashira–Click and Click–Heck reactions
  作者：Cybille Rossy、Jérôme Majimel、Mona Tréguer Delapierre、Eric Fouquet、François-Xavier Felpin

  DOI：10.1016/j.jorganchem.2014.01.006

  日期：2014.4

  This paper describes the development of one-pot sequential Sonogashira-Click and Click-Heck reactions by using Pd-Cu/C as a heterogeneous multi-task catalyst for the synthesis of heterocyclic structures. Details of the optimization studies and the substrate scope are discussed. These methodologies allow the preparation of functionalized triazoles in simple experimental conditions with inexpensive reagents. (C) 2014 Elsevier B. V. All rights reserved.
• An easy synthetic approach to 1,2,3-triazole-fused heterocycles
  作者：Vito Fiandanese、Giuseppe Marchese、Angela Punzi、Francesco Iannone、Giacomo G. Rafaschieri

  DOI：10.1016/j.tet.2010.09.068

  日期：2010.11

  A convenient synthesis of 1,2,3-triazole-fused isoindolines and dihydroisoquinolines in good to excellent yield is reported, starting from easily available terminal alkynes and (2-haloaryl)alkylazides. The method is based upon a cycloaddition reaction, via click chemistry, followed by a transition metal-catalyzed functionalization of a C-H bond. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.