5,6-dimethoxy-1-phenyl-1H-indazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5,6-dimethoxy-1-phenyl-1H-indazole
• 英文别名: 5,6-Dimethoxy-1-phenylindazole
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: PQCVRAIGXOWXMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-溴藜芦醛 在 copper(l) iodide trans-1,2-diaminomethyl-cyclohexane 、 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 0.34h， 生成 5,6-dimethoxy-1-phenyl-1H-indazole
  参考文献：
  名称：

  Microwave-assisted synthesis of 1-aryl-1H-indazoles via one-pot two-step Cu-catalyzed intramolecular N-arylation of arylhydrazones

  摘要：

  A highly efficient one-pot two-step microwave procedure was developed for the synthesis of 1-aryl-1H-indazoles. Microwave heating of 2-halobenzaldehydes or 2-haloacetophenones with phenylhydrazines at 160 degrees C for 10 min quantitatively yielded the arylhydrazones, which were further cyclized to give 1-aryl-1H-indazoles via CuI/diamine-catalyzed N-arylation under microwave heating (160 degrees C, 10min). Good to excellent yields were observed for 2-iodo, 2-bromo, and 2-chloro benzaldehydes or acetophenones. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.143

文献信息

• Copper(I) salt/PEG-400 catalysis in one-pot direct synthesis of 1-aryl-1<i>H</i>-indazoles from 2-bromobenzaldehydes and arylhydrazines
  作者：Yeon Kyu Bae、Chan Sik Cho

  DOI：10.1002/aoc.2956

  日期：2013.4

  2‐Bromobenzaldehydes are condensed and cyclized with arylhydrazines (or their hydrochlorides) in PEG‐400 at 110 °C in the presence of a catalytic amount of a copper(I) salt along with a base to give 1‐aryl‐1H‐indazoles in high yields. Copyright © 2013 John Wiley & Sons, Ltd.

  将2-溴苯甲醛在催化量的铜（I）盐和碱存在下于110°C下与芳肼（或其盐酸盐）缩合并与PEG-400环合，得到1-芳基-1 H吲唑高产。版权所有©2013 John Wiley＆Sons，Ltd.
• Facile palladium-catalysed synthesis of 1-aryl-1H-indazoles from 2-bromobenzaldehydes and arylhydrazines
  作者：Chan Sik Cho、Dong Kwon Lim、Nam Ho Heo、Tae-Jeong Kim、Sang Chul Shim

  DOI：10.1039/b312154m

  日期：——

  2-Bromobenzaldehydes react with arylhydrazines in toluene at 100 [degree]C in the presence of a catalytic amount of a palladium catalyst and phosphorus chelating ligands such as 1,1[prime or minute]-bis(diphenylphosphino)ferrocene and 1,3-bis(diphenylphosphino)propane along with NaO-t-Bu to afford 1-aryl-1H-indazoles in good yields.

  2-溴苯甲醛在催化量的钯催化剂和磷螯合配体（例如1,1 [伯或分钟]-双（二苯基膦基）二茂铁和1,3-）的存在下于100℃与芳肼在甲苯中反应双（二苯基膦基）丙烷与NaO-t-Bu一起以高收率得到1-芳基-1H-吲唑。
• Synthesis of 1-Aryl-1<i>H</i> -indazoles via a Ligand-Free Copper- Catalyzed Intramolecular Amination Reaction
  作者：Mingshan Gao、Xiujie Liu、Xianyang Wang、Qian Cai、Ke Ding

  DOI：10.1002/cjoc.201190223

  日期：2011.6

  A general synthesis of 1‐aryl‐1‐H‐indazoles from o‐halogenated aryl aldehydes or ketones and aryl hydrazines was described. This protocol included an intermolecular condensation and a ligand‐free copper‐catalyzed intramolecular Ullmann‐type coupling reaction. This method was applied to a wide range of substrates to produce the indazole products in good yields.

  描述了由邻卤代的芳基醛或酮和芳基肼合成1-芳基-1- H-吲唑的一般方法。该方案包括分子间缩合和无配体的铜催化的分子内Ullmann型偶联反应。该方法适用于多种底物，以高收率生产吲唑产品。
• Copper Powder–Catalyzed C-N Bond Formation of Arylhydrazones of 2-Bromobenzaldehydes Leading to 1-Aryl-1<i>H</i>-indazoles
  作者：Hye Kyung Lee、Chan Sik Cho

  DOI：10.1080/00397911.2011.614714

  日期：2013.2.1

  Arylhydrazones of 2-bromobenzaldehydes and its analogs are cyclized in PEG-400 at 110 degrees C in the presence of a catalytic amount of copper powder along with NaOtBu to give 1-aryl-1H-indazole derivatives in good yields.
• Microwave-assisted synthesis of 1-aryl-1H-indazoles via one-pot two-step Cu-catalyzed intramolecular N-arylation of arylhydrazones
  作者：Chittari Pabba、Hong-Jun Wang、Susan R. Mulligan、Zhen-Jia Chen、Todd M. Stark、Brian T. Gregg

  DOI：10.1016/j.tetlet.2005.08.143

  日期：2005.10

  A highly efficient one-pot two-step microwave procedure was developed for the synthesis of 1-aryl-1H-indazoles. Microwave heating of 2-halobenzaldehydes or 2-haloacetophenones with phenylhydrazines at 160 degrees C for 10 min quantitatively yielded the arylhydrazones, which were further cyclized to give 1-aryl-1H-indazoles via CuI/diamine-catalyzed N-arylation under microwave heating (160 degrees C, 10min). Good to excellent yields were observed for 2-iodo, 2-bromo, and 2-chloro benzaldehydes or acetophenones. (c) 2005 Elsevier Ltd. All rights reserved.