1-(2-bromoquinolin-3-ylmethyl)pyrrole-2-carboxylic acid diethyl amide | 524024-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(2-bromoquinolin-3-ylmethyl)pyrrole-2-carboxylic acid diethyl amide
• 英文别名: 1-[(2-bromoquinolin-3-yl)methyl]-N,N-diethylpyrrole-2-carboxamide
• CAS: 524024-92-8
• 化学式: C₁₉H₂₀BrN₃O
• 分子量: 386.291
• InChiKey: URNPJJXXRSMCFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  38.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-bromoquinolin-3-ylmethyl)pyrrole-2-carboxylic acid diethyl amide 在 copper(l) iodide 、 正丁基锂 、 sodium iodide 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 为溶剂， 反应 16.08h， 生成 11H-pyrrolo[1,2-b]acridin-4-one
  参考文献：
  名称：

  Intramolecular cyclisation of functionalised heteroaryllithiums. Synthesis of novel indolizinone-based compounds

  摘要：

  The intramolecular cyclisation of heteroaryllithiums derived from N-heteroarylmethylpyrrole-2-carboxam ides takes place smoothly at low temperature when N-methoxy-N-methyl and morpholine amides are used as internal electrophiles. Halogen-lithium exchange using n-BuLi is the method of choice to achieve metalation on the quinoline and pyridine derivatives, while directed lithiation (LDA) works better for furan. In the case of thiophene both methodologies can be applied. These metalation-cyclisation sequences provide a useful entry to several types of indolizidine based compounds (pyrrolo[1,2-b]acridinones, pyrrolo[1,2-g]quinolones, thieno and furo[3,2-f]indolizinones). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.057
• 作为产物：
  描述：

  (2-氯-3-喹啉)甲醇 在 氢氧化钾 、 三溴化磷 作用下， 以 二甲基亚砜 为溶剂， 反应 19.0h， 生成 1-(2-bromoquinolin-3-ylmethyl)pyrrole-2-carboxylic acid diethyl amide
  参考文献：
  名称：

  Intramolecular cyclisation of functionalised heteroaryllithiums. Synthesis of novel indolizinone-based compounds

  摘要：

  The intramolecular cyclisation of heteroaryllithiums derived from N-heteroarylmethylpyrrole-2-carboxam ides takes place smoothly at low temperature when N-methoxy-N-methyl and morpholine amides are used as internal electrophiles. Halogen-lithium exchange using n-BuLi is the method of choice to achieve metalation on the quinoline and pyridine derivatives, while directed lithiation (LDA) works better for furan. In the case of thiophene both methodologies can be applied. These metalation-cyclisation sequences provide a useful entry to several types of indolizidine based compounds (pyrrolo[1,2-b]acridinones, pyrrolo[1,2-g]quinolones, thieno and furo[3,2-f]indolizinones). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.057

文献信息

• Parham-Type Cycliacylation with Weinreb Amides. Application to the Synthesis of Fused Indolizinone Systems
  作者：Javier Ruiz、Nuria Sotomayor、Esther Lete

  DOI：10.1021/ol034194+

  日期：2003.4.1

  [GRAPHIC]Weinreb amides behave as efficient internal electrophiles in Parham-type cycliacylation reactions. Thus, aryl- and heteroaryllithiums generated by lithium-halogen exchange undergo intramolecular cyclization to give fused indolizinone systems as pyrrolo[1,2-b]isoquinolines, thieno[2,3-f]indolizinones, and pyrrolo[1,2-b]acridinones in high yields.
• Intramolecular cyclisation of functionalised heteroaryllithiums. Synthesis of novel indolizinone-based compounds
  作者：Javier Ruiz、Esther Lete、Nuria Sotomayor

  DOI：10.1016/j.tet.2006.04.057

  日期：2006.6

  The intramolecular cyclisation of heteroaryllithiums derived from N-heteroarylmethylpyrrole-2-carboxam ides takes place smoothly at low temperature when N-methoxy-N-methyl and morpholine amides are used as internal electrophiles. Halogen-lithium exchange using n-BuLi is the method of choice to achieve metalation on the quinoline and pyridine derivatives, while directed lithiation (LDA) works better for furan. In the case of thiophene both methodologies can be applied. These metalation-cyclisation sequences provide a useful entry to several types of indolizidine based compounds (pyrrolo[1,2-b]acridinones, pyrrolo[1,2-g]quinolones, thieno and furo[3,2-f]indolizinones). (c) 2006 Elsevier Ltd. All rights reserved.