1-methyl-5-phenylpyrazolo[5,1-a]isoquinoline | 1262639-23-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-methyl-5-phenylpyrazolo[5,1-a]isoquinoline
• CAS: 1262639-23-5
• 化学式: C₁₈H₁₄N₂
• 分子量: 258.323
• InChiKey: GQAVRMJDHXBYAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲基吡唑 、 1-溴-2-苯基乙炔-苯 在 copper(l) iodide 、 2,6-二乙基苯胺 、 1,3-bis(2,6-diethylphenyl)-1H-imidazol-3-ium chloride 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 以45%的产率得到1-methyl-5-phenylpyrazolo[5,1-a]isoquinoline
  参考文献：
  名称：

  Route to Pyrazolo[5,1-a]isoquinolines via a Copper-Catalyzed Tandem Reaction of 2-Alkynylbromobenzene with Pyrazole

  摘要：

  A copper-catalyzed tandem reaction of 2-alkynylbromobenzene and pyrazole is described that provides a facile route to pyrazolo[5,1-a]isoquinolines in good yields. During the reaction process, copper(1)-catalyzed hydroamination and C-H activation are involved.

  DOI：

  10.1021/jo400523v

文献信息

• Synthesis of H-pyrazolo[5,1-a]isoquinolines via a silver triflate-catalyzed tandem reaction of N′-(2-alkynylbenzylidene)hydrazide with alcohol
  作者：Wenyan Hao、Tinli Zhang、Mingzhong Cai

  DOI：10.1016/j.tet.2013.08.049

  日期：2013.11

  A silver triflate-catalyzed tandem reaction of N′-(2-alkynylbenzylidene)hydrazide with alcohol is reported, which generates H-pyrazolo[5,1-a]isoquinoline derivatives in good yields under mild conditions.

  的三氟甲磺酸银催化的串联反应Ñ ' - （2- alkynylbenzylidene）与醇酰肼报道，其产生ħ -吡唑并[5,1-一个在温和的条件下良好的产率]异喹啉衍生物。
• Palladium-catalyzed oxidation of amine in air: an efficient approach to H-pyrazolo[5,1-a]-isoquinolines
  作者：Jie Sheng、Ying Guo、Jie Wu

  DOI：10.1016/j.tet.2013.05.066

  日期：2013.8

  An efficient approach to H-pyrazolo[5,1-a]isoquinolines through a reaction of N'-(2-alkynylbenzylidene) hydrazide with amine in the presence of a cooperative catalysis under mild conditions is reported. The palladium-catalyzed oxidation of amine in air leading to the formation of enamine is the key step during the transformation. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of <i>H</i>-Pyrazolo[5,1-<i>a</i>]isoquinolines via Copper(II)-Catalyzed Oxidation of an Aliphatic C−H Bond of Tertiary Amine in Air
  作者：Shaoyu Li、Jie Wu

  DOI：10.1021/ol102939r

  日期：2011.2.18

  A multicomponent reaction of 2-alkynylbenzaldehyde, sulfonohydrazide, and tertiary amine is discovered, which generates the unexpected H-pyrazolo[5,1-a]isoquinolines in good yields under mild conditions. In the reaction process, silver(I)-catalyzed intramolecular cyclization and copper(II)-catalyzed oxidation of an aliphatic C-H bond of tertiary amine in air are involved.
• Silver Triflate-Palladium Chloride Cooperative Catalysis in a Tandem Reaction for the Synthesis of<i>H</i>-Pyrazolo[5,1-<i>a</i>]isoquinolines
  作者：Qing Xiao、Jie Sheng、Qiuping Ding、Jie Wu

  DOI：10.1002/adsc.201300327

  日期：2013.8.12

  AbstractA tandem reaction of N′‐(2‐alkynylbenzylidene)hydrazone with alcohol in the presence of oxygen co‐catalyzed by silver triflate and palladium chloride under mild conditions is reported, providing H‐pyrazolo[5,1‐a]isoquinolines in good yields. During the transformation, isoquinolinium‐2‐yl amide was the key intermediate via a silver(I)‐catalyzed 6‐endo cyclization of N′‐(2‐alkynylbenzylidene)hydrazone. The presence of a palladium catalyst and molecular oxygen promoted the oxidation of the alcohol to the aldehyde or ketone. Subsequent nucleophilic attack of the in situ generated enolate to isoquinolinium‐2‐yl amide, intramolecular condensation, and aromatization afforded the H‐pyrazolo[5,1‐a]isoquinolines. The easily available starting materials, good substrate generality, mild reaction conditions, and experimental ease should make this method attractive for further library construction.magnified image