(4-bromo-3-phenylisoquinolin-2-ium-2-yl)(tosyl)amide | 1112200-32-4

• 英文名称: (4-bromo-3-phenylisoquinolin-2-ium-2-yl)(tosyl)amide
• CAS: 1112200-32-4
• 化学式: C₂₂H₁₇BrN₂O₂S
• 分子量: 453.359
• InChiKey: XCAQTIUGNFADRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  (4-bromo-3-phenylisoquinolin-2-ium-2-yl)(tosyl)amide 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (E)-butyl 3-(1-(methoxy(phenyl)methyl)-5-phenylpyrazolo[5,1-a]isoquinolin-6-yl)acrylate
  参考文献：
  名称：

  Rapid Access to H-Pyrazolo[5,1-a]isoquinolines via Sequential Reaction of N′-(2-Alkynylbenzylidene)hydrazides

  摘要：

  通过N′-(2-炔基苄叉)酰肼的连续反应，高效合成了多种H-吡唑并[5,1-a]异喹啉。从N′-(2-炔基苄叉)酰肼与溴生成的含溴异喹啉鎓，在温和条件下与α,β-不饱和醛和甲醇反应，得到中等至良好产率的6-溴-1-(甲氧基甲基)-H-吡唑并[5,1-a]异喹啉。通过钯催化的铃木-宫浦偶联或赫克反应进一步修饰，得到多种H-吡唑并[5,1-a]异喹啉化合物。

  DOI：

  10.1055/s-0030-1259704
• 作为产物：
  描述：

  2-phenylethynylbenzaldehyde p-toluenesulphonylhydrazone 在 溴 作用下， 以 二氯甲烷 为溶剂， 生成 (4-bromo-3-phenylisoquinolin-2-ium-2-yl)(tosyl)amide
  参考文献：
  名称：

  通过N '-（2-炔基亚苄基）酰肼的顺序反应 合成官能化的H-吡唑并[5,1- a ]异喹啉†

  摘要：

  描述了通过N '-（2-炔基亚苄基）酰肼的顺序反应，以多样性为导向的功能化H-吡唑并[5,1- a ]异喹啉合成方法。溴介导的亲电环化，Ag催化的炔炔亲核加成和钯催化的交叉偶联反应均参与了转化。

  DOI：

  10.1039/b914265g

文献信息

• Three-component reaction of N′-(2-alkynylbenzylidene)hydrazide, α,β-unsaturated carbonyl compound, with bromine
  作者：Hui Ren、Shengqing Ye、Fen Liu、Jie Wu

  DOI：10.1016/j.tet.2010.08.052

  日期：2010.10

  different conditions for the three-component reaction of N′-(2-alkynylbenzylidene)hydrazide, α,β-unsaturated carbonyl compound, with bromine. 6-BromoH-pyrazolo[5,1-a]isoquinoline was obtained when the reaction was performed in NMP at 70 °C in the presence of DABCO as base, while 6-bromo-1,2,3,10b-tetrahydropyrazolo[5,1-a]isoquinoline was afforded when the reaction occurred in DMAc at 10 °C in the presence

  N '-（2-炔基亚苄基）酰肼，α，β-不饱和羰基化合物与溴的三组分反应在不同条件下产生了不同的结果。当以DABCO为碱在70°C下于NMP中于NMP中进行反应时，获得了6-溴H-吡唑并[5,1- a ]异喹啉，而6-溴-1,2,3,10 b-四氢吡唑并已获得了6-溴H-吡唑并[5,1- a ]异喹啉。当反应在10 K的DMAc中以K 3 PO 4为碱存在时，提供[5,1- a ]异喹啉。
• Generation of diverse 1-(isoquinolin-1-yl)guanidines via a sequential multi-component/cross-coupling reaction
  作者：Chao Ye、Zhiyuan Chen、Huanhuan Wang、Jie Wu

  DOI：10.1016/j.tet.2012.03.081

  日期：2012.7

  A multi-component reaction of 2-alkynylbenzaldehyde, 4-methylbenzenesulfonohydrazide, carbodiimide, and bromine is reported, which generates 1-(4-bromoisoquinolin-1-yl)guanidines in good yields under mild conditions. The products could be further elaborated via a palladium-catalyzed Suzuki Miyaura coupling reaction, leading to the diverse 1-(isoquiriolin-1-yl)guanidines. (C) 2012 Elsevier Ltd. All rights reserved.
• An efficient route to diverse H-pyrazolo[5,1-a]isoquinolines via sequential multi-component/cross-coupling reactions
  作者：Xingxin Yu、Xiaolin Pan、Jie Wu

  DOI：10.1016/j.tet.2010.12.005

  日期：2011.2

  Multi-component reaction of 2-alkynylbenzaldehyde, sulfonohydrazide, electrophile (bromine or iodine), and ketone or aldehyde under mild conditions proceeds smoothly to afford the functionalized H-pyrazolo[5,1-a]isoquinolines in good yields. This one-pot process involves intermolecular condensation, electrophilic cyclization, nucleophilic addition, intramolecular condensation, and aromatization. The resulting halo-containing H-pyrazolo[5,1-a]isoquinolines could be further elaborated via palladium-catalyzed cross-coupling reactions. (C) 2010 Elsevier Ltd. All rights reserved.
• Highly efficient electrophilic cyclization of N′-(2-alkynylbenzylidene)hydrazides
  作者：Qiuping Ding、Zhiyuan Chen、Xingxin Yu、Yiyuan Peng、Jie Wu

  DOI：10.1016/j.tetlet.2008.11.006

  日期：2009.1

  Electrophilic cyclization of N'-(2-alkynylbenzylidene)hydrazides with I-2, Br-2, or ICl under mild conditions is described. This reaction proceeds smoothly in dichloromethane at room temperature, which provides a useful method for the synthesis of functionalized isoquinolinium-2-yl amide. (C) 2008 Elsevier Ltd. All rights reserved.