6-methoxy-N-benzoyliminoquinolinium ylide | 1337984-75-4

• 英文名称: 6-methoxy-N-benzoyliminoquinolinium ylide
• CAS: 1337984-75-4
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: FRMFTJPBSVFGCS-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：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  E-styryl iodide 、 6-methoxy-N-benzoyliminoquinolinium ylide 在 palladium bromide 、 三(4-甲氧苯基)膦 、 silver benzoate 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以69%的产率得到7-methoxy-2-phenylpyrazolo[1,5-a]quinoline
  参考文献：
  名称：

  Synthesis of 2- and 2,3-Substituted Pyrazolo[1,5-a]pyridines: Scope and Mechanistic Considerations of a Domino Direct Alkynylation and Cyclization of N-Iminopyridinium Ylides Using Alkenyl Bromides, Alkenyl Iodides, and Alkynes

  摘要：

  Direct functionalization and tandem processes have both received considerable recent interest due to their cost and time efficiency. Herein we report the synthesis of difficult to obtain 2-substituted pyrazolo[1,5-a]pyridines through a tandem palladium-catalyzed/silver-mediated elimination/direct functionalization/cyclization reaction involving N-benzoyliminopyridinium ylides. As such, these biologically important molecules are prepared in an efficient, high-yielding manner, only requiring a two-step sequence from pyridine. Aryl-substituted alkenyl bromides and iodides are effective ylide coupling partners. Mechanistic studies led to the use of terminal alkynes, which extended the scope of the reaction to include alkyl substitution on the unsaturated reactive site. The optimization, scope, and mechanistic considerations of the process are discussed.

  DOI：

  10.1021/jo201303x
• 作为产物：
  描述：

  6-甲氧基喹啉 在 2,4-二硝基苯基羟胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.5h， 生成 6-methoxy-N-benzoyliminoquinolinium ylide
  参考文献：
  名称：

  Synthesis of 2- and 2,3-Substituted Pyrazolo[1,5-a]pyridines: Scope and Mechanistic Considerations of a Domino Direct Alkynylation and Cyclization of N-Iminopyridinium Ylides Using Alkenyl Bromides, Alkenyl Iodides, and Alkynes

  摘要：

  Direct functionalization and tandem processes have both received considerable recent interest due to their cost and time efficiency. Herein we report the synthesis of difficult to obtain 2-substituted pyrazolo[1,5-a]pyridines through a tandem palladium-catalyzed/silver-mediated elimination/direct functionalization/cyclization reaction involving N-benzoyliminopyridinium ylides. As such, these biologically important molecules are prepared in an efficient, high-yielding manner, only requiring a two-step sequence from pyridine. Aryl-substituted alkenyl bromides and iodides are effective ylide coupling partners. Mechanistic studies led to the use of terminal alkynes, which extended the scope of the reaction to include alkyl substitution on the unsaturated reactive site. The optimization, scope, and mechanistic considerations of the process are discussed.

  DOI：

  10.1021/jo201303x

文献信息

• Copper-Catalyzed Cross-Dehydrogenative Coupling of<i>N</i>-Iminoquinolinium Ylides with Secondary Amines
  作者：Zerui Hua、Lei Fang、Shengying Wu、Limin Wang

  DOI：10.1002/ejoc.201600905

  日期：2016.10

  The copper-catalyzed cross-dehydrogenative coupling of N-iminoquinolinium ylides with secondary amines led to ortho-amino-substituted quinoline derivatives with high levels of regioselectivity in good yields. This direct C–H bond amination transformation employs CuI as the catalyst without the use of a ligand, external oxidant, or base. The reaction is operationally simple and can be conducted under

  N-亚氨基喹啉鎓叶立德与仲胺的铜催化交叉脱氢偶联导致邻氨基取代的喹啉衍生物具有高水平的区域选择性和良好的产率。这种直接的 C-H 键胺化转化使用 CuI 作为催化剂，而不使用配体、外部氧化剂或碱。该反应操作简单，可在温和条件下进行。无需任何额外步骤即可去除 N-苯甲酰基导向基团。