Pyrazin-1-ium-1-ylazanide | 59139-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: Pyrazin-1-ium-1-ylazanide
• CAS: 59139-50-3
• 化学式: C₄H₅N₃
• 分子量: 95.1038
• InChiKey: RAGXSKIJAKUIFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  五氟吡啶 、 Pyrazin-1-ium-1-ylazanide 以 N,N-二甲基甲酰胺 为溶剂， 生成 (pyrazin-1-ium-1-yl)(perfluoropyridin-4-yl)amide
  参考文献：
  名称：

  Molecular and crystal structure of (pyrazin-1-ium-1-yl)(perfluoropyridin-4-yl) and (4,4′-bipyridin-1-ium-1-yl)(perfluoropyridin-4-yl)amides

  摘要：

  The single crystal X-ray diffraction study of (pyrazin-1-ium-1-yl)(perfluoropyridin-4-yl) and (4,4'-bipyridin)-1-ium-1-yl(perfluoropyridin-4-yl)amides is performed. In all cases, the N+-N- bond length is less than that of the single N-planar.-N-planar. bond, but considerably more than that of the double N=N bond, which indicates a weak involvement of the N- lone pair of the C5NF4N- group in conjugation with pyrazine or bipyridine moieties. Quantum chemical calculations by DFT/(PBE/L1), B3LYP/L1, and RI-MP2/L1 methods provide the geometry of amides similar to the experimental one. Crystals of (pyrazin-1-ium-1-yl)(perfluoropyridin-4-yl)amide form stacks mainly through F-pi interactions. The stacks are joined in 3D architecture by weak C-HaEuro broken vertical bar N and C-HaEuro broken vertical bar F hydrogen bonds. In the case of (4,4'-bipyridin)-1-ium-1-yl(perfluoropyridin-4-yl)amide crystals, an essential role is played by the pi stacking interactions of heteroaromatic rings.

  DOI：

  10.1134/s0022476612050186
• 作为产物：
  描述：

  N-aminopyrazinium mesitylene sulfonate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 Pyrazin-1-ium-1-ylazanide
  参考文献：
  名称：

  Molecular and crystal structure of (pyrazin-1-ium-1-yl)(perfluoropyridin-4-yl) and (4,4′-bipyridin-1-ium-1-yl)(perfluoropyridin-4-yl)amides

  摘要：

  The single crystal X-ray diffraction study of (pyrazin-1-ium-1-yl)(perfluoropyridin-4-yl) and (4,4'-bipyridin)-1-ium-1-yl(perfluoropyridin-4-yl)amides is performed. In all cases, the N+-N- bond length is less than that of the single N-planar.-N-planar. bond, but considerably more than that of the double N=N bond, which indicates a weak involvement of the N- lone pair of the C5NF4N- group in conjugation with pyrazine or bipyridine moieties. Quantum chemical calculations by DFT/(PBE/L1), B3LYP/L1, and RI-MP2/L1 methods provide the geometry of amides similar to the experimental one. Crystals of (pyrazin-1-ium-1-yl)(perfluoropyridin-4-yl)amide form stacks mainly through F-pi interactions. The stacks are joined in 3D architecture by weak C-HaEuro broken vertical bar N and C-HaEuro broken vertical bar F hydrogen bonds. In the case of (4,4'-bipyridin)-1-ium-1-yl(perfluoropyridin-4-yl)amide crystals, an essential role is played by the pi stacking interactions of heteroaromatic rings.

  DOI：

  10.1134/s0022476612050186

文献信息

• Synthesis of 2- and 2,3-Substituted Pyrazolo[1,5-<i>a</i>]pyridines: Scope and Mechanistic Considerations of a Domino Direct Alkynylation and Cyclization of <i>N</i>-Iminopyridinium Ylides Using Alkenyl Bromides, Alkenyl Iodides, and Alkynes
  作者：James J. Mousseau、James A. Bull、Carolyn L. Ladd、Angélique Fortier、Daniela Sustac Roman、André B. Charette

  DOI：10.1021/jo201303x

  日期：2011.10.21

  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.