5-benzylindolo[1,2-c]quinazolin-6(5H)-one | 857090-93-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5-benzylindolo[1,2-c]quinazolin-6(5H)-one
• 英文别名: 5-Benzylindolo[1,2-c]quinazolin-6-one
• CAS: 857090-93-8
• 化学式: C₂₂H₁₆N₂O
• 分子量: 324.382
• InChiKey: XXBDDRBJWCPRIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-benzylindolo[1,2-c]quinazolin-6(5H)-one 在 sodium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 24.0h， 生成 N-(2-(1H-indol-2-yl)phenyl)-N-benzylchloroacetamide
  参考文献：
  名称：

  An iodoacetamide-based free radical cyclisation approach to the 7,12-dihydro-indolo[3,2-d][1]benzazepin-6(5H)-one (paullone) system

  摘要：

  A potentially versatile route to 2-(2-aminoaryl)indoles is described based on a palladium-mediated cyclisation of N-substituted indoles, together with free radical cyclisation of their N-benzyliodoacetamide derivatives to the 7,12-dihydro-indolo[3,2-d][l]berizazepin-6(5H)-one system. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.133
• 作为产物：
  描述：

  N-(2-bromophenyl)-1H-indole-1-carboxamide 在 palladium diacetate 叔丁胺氢碘酸盐 、 叔丁胺氢溴酸盐 、 sodium hydride 、 potassium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 5-benzylindolo[1,2-c]quinazolin-6(5H)-one
  参考文献：
  名称：

  An iodoacetamide-based free radical cyclisation approach to the 7,12-dihydro-indolo[3,2-d][1]benzazepin-6(5H)-one (paullone) system

  摘要：

  A potentially versatile route to 2-(2-aminoaryl)indoles is described based on a palladium-mediated cyclisation of N-substituted indoles, together with free radical cyclisation of their N-benzyliodoacetamide derivatives to the 7,12-dihydro-indolo[3,2-d][l]berizazepin-6(5H)-one system. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.133

文献信息

• Palladium-Catalyzed C12-Selective Direct Arylation of [1,2-c]Quinazolin-6(5H)-ones
  作者：Antonio Arcadi、Sandro Cacchi、Giancarlo Fabrizi、Andrea Fochetti、Francesca Ghirga、Antonella Goggiamani、Antonia Iazzetti、Fabio Marinelli

  DOI：10.1055/s-0037-1610711

  日期：2019.9

  12-arylindolo[1,2-c]quinazolin-6(5H)-ones through the palladium-catalyzed direct arylation of N-benzyl and NH-free [1,2-c]quinazolin-6(5H)-ones with aryl halides is described. A straightforward approach to the synthesis of the challenging 12-arylindolo[1,2-c]quinazolin-6(5H)-ones through the palladium-catalyzed direct arylation of N-benzyl and NH-free [1,2-c]quinazolin-6(5H)-ones with aryl halides is described

  抽象的 通过钯催化的N-苄基和不含NH [1,2- c ]的直接芳基化反应来合成具有挑战性的12-芳基吲哚并[1,2- c ]喹唑啉-6（5 H）-的简单方法描述了带有芳基卤化物的喹唑啉-6（5 H）-1 。 通过钯催化的N-苄基和不含NH [1,2- c ]的直接芳基化反应来合成具有挑战性的12-芳基吲哚并[1,2- c ]喹唑啉-6（5 H）-的简单方法描述了带有芳基卤化物的喹唑啉-6（5 H）-1 。
• One-Pot Synthesis of Pyrimido[1,6-<i>a</i>]indol-1(2<i>H</i>)-one Derivatives by a Nucleophilic Addition/Cu-Catalyzed N-Arylation/Pd-Catalyzed C−H Activation Sequential Process
  作者：Zhi-Jing Wang、Jian-Guo Yang、Fan Yang、Weiliang Bao

  DOI：10.1021/ol101041e

  日期：2010.7.2

  A novel and convenient one-pot synthesis of pyrimido[1,6-a]indol-1(2H)-one derivatives through a nucleophilic addition/Cu-catalyzed N-arylation/Pd-catalyzed C H activation sequential process is described. The reaction of easily prepared ortho-gem-dibromovinyl isocyanates with N-alkylanilines gave the desired indole derivatives in moderate to good yields.
• An iodoacetamide-based free radical cyclisation approach to the 7,12-dihydro-indolo[3,2-d][1]benzazepin-6(5H)-one (paullone) system
  作者：John B. Bremner、Waya Sengpracha

  DOI：10.1016/j.tet.2005.03.133

  日期：2005.6

  A potentially versatile route to 2-(2-aminoaryl)indoles is described based on a palladium-mediated cyclisation of N-substituted indoles, together with free radical cyclisation of their N-benzyliodoacetamide derivatives to the 7,12-dihydro-indolo[3,2-d][l]berizazepin-6(5H)-one system. (c) 2005 Elsevier Ltd. All rights reserved.