(pyridin-1-iumyl)[(pyrazin-2-yl)aminide] | 157020-17-2

• 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: (pyridin-1-iumyl)[(pyrazin-2-yl)aminide]
• 英文别名: N-(pyrazin-2'-yl)pyridinium aminide；N-(pyrazin-2-yl)pyridinium aminide；pyridinium (N-2'-pyrazinyl)aminide；pyridinium N-(2'-pyrazinyl)aminide；Pyrazin-2-yl(pyridin-1-ium-1-yl)azanide
• CAS: 157020-17-2
• 化学式: C₉H₈N₄
• 分子量: 172.189
• InChiKey: ABIJGPCVMXOPPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (pyridin-1-iumyl)[(pyrazin-2-yl)aminide] 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 N-(3',5'-dibromopyrazin-2'-yl)pyridinium aminide
  参考文献：
  名称：

  A New Class of Pyrazolopyridine Nucleus with Fluorescent Properties, Obtained through Either a Radical or a Pd Arylation Pathway from N-Azinylpyridinium N-Aminides

  摘要：

  The synthesis of dipyridopyrazole and pyridopyrazolopyrazine derivatives--both of which incorporate a 3-aryl moiety--can be achieved in moderate yields by intramolecular radical arylation of pyridinium N-aminides using tris(trimethylsilyl)silane and azobisisobutyronitrile. Improved results were obtained on using Pd direct arylation in conjunction with microwave irradiation. A preliminary study into the fluorescent properties of the target compounds is also reported.

  DOI：

  10.1021/jo801549u
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 (pyridin-1-iumyl)[(pyrazin-2-yl)aminide]
  参考文献：
  名称：

  Pyridinium N-(2′-Azinyl)Aminides: Regioselective Synthesis of 2-Alkylaminoazines

  摘要：

  The regioselective alkylation of pyridinium-N-(2'-azinil)aminides with alkyl halides under mild conditions is described. The alkylation, combined with a reduction of the N-N bond, allows an easy preparation of 2-alkylaminoazines. (C) 2000 Elsevier Science Ltd. AU rights reserved.

  DOI：

  10.1016/s0040-4020(00)00084-3

文献信息

• Azinium-N-(2′-azinyl)aminides: synthesis, structure and reactivity
  作者：Rosa Carceller、Jose L. García-Navío、María L. Izquierdo、Julio Alvarez-Builla、Mariano Fajardo、Pilar Gómez-Sal、Federico Gago

  DOI：10.1016/s0040-4020(01)90411-9

  日期：1994.4

  Several azinium-N-(2′-azinyl)aminides are reported. The structure of pyridinium-N-(2′-pyridyl)aminide has been studied, both in solution and in crystalline state, and results have been compared. In non-polar solvents, the aminides present a planar conformation stabilized by an intramolecular hydrogen bond. The reactivity toward electrophiles confirms the structural data, producing either N- or C- substitutions

  报道了几种叠氮基-N-（2'-叠氮基）酰胺。研究了吡啶鎓-N-（2'-吡啶基）氨基化物在溶液和结晶状态下的结构，并对结果进行了比较。在非极性溶剂中，这些胺化物具有通过分子内氢键稳定的平面构象。对亲电子试剂的反应性证实了结构数据，在温和条件下可产生N-或C-取代。
• Regioselective Synthesis of 2-Amino-5-(or 3-)arylazo-Substituted Pyridines and Pyrazines from Pyridinium<i>N</i>-Aminides
  作者：Elena Gala、M. José Reyes、Julio Alvarez-Builla、M. Luisa Izquierdo

  DOI：10.1002/ejoc.201600059

  日期：2016.4

  Differently modified 2-aminopyridines and pyrazines bearing an arylazo group at the 3- or 5-position have been generated from pyridinium N-aminides in a regioselective fashion. The detailed chemistry starts with attack of the N-aminide on a diazonium salt, to form the arylazo derivative. N-alkylation on the exocyclic nitrogen and reduction to break the N–N bond then affords the final compounds, as

  已经以区域选择性方式从吡啶鎓 N-胺化物生成了在 3 位或 5 位带有芳基偶氮基的不同修饰的 2-氨基吡啶和吡嗪。详细的化学反应从 N-胺对重氮盐的攻击开始，形成芳基偶氮衍生物。环外氮上的 N-烷基化和还原以破坏 N-N 键，然后提供最终化合物，作为吡啶鎓 N-胺化物广泛合成用途的延伸。
• N-Azinylpyridinium N-Aminides: An Approach to Pyrazolopyridines via an Intramolecular Radical Pathway
  作者：Araceli Nuñez、Aránzazu García de Viedma、Valentín Martínez-Barrasa、Carolina Burgos、Julio Alvarez-Builla

  DOI：10.1055/s-2002-32596

  日期：——

  has been devoted to pyridyl radicals; both Snieckus 3 and Nadin 4 have reported pyridyl radical cyclisations. Harrowven 5 has published some papers, which include pyridyl radical cyclisations and aryl radical cyclisations onto pyridines. Jones 6 has disclosed the use of radicals derived from 3-bromopyridine and the exten- sion of this chemistry to pyridinium radicals. 7 However, to the best of our

  描述了分子内自由基芳基化，在热条件下，连接到过量的 2-azinyliminopyridine 部分的 - 缺陷的吡啶鎓。该方法允许新进入吡唑并(1,5-a)吡啶核。使用三正丁基氢化锡 (Bu3SnH) 和偶氮二异丁腈 (AIBN) 衍生自芳基卤化物的芳基自由基的生成和后续反应现已得到充分记录，并且已经报道了几种基于芳基自由基环化的合成。1 杂芳基的几个例子是已知的，据推测它们的行为与芳基相似，因为孤电子将位于与芳族系统正交的轨道上，因此，它的性质（-过量或-不足）应该具有对这些自由基的反应性影响很小或没有影响。2 特别关注吡啶基；Snieckus 3 和 Nadin 4 都报道了吡啶基自由基环化。Harrowven 5 发表了一些论文，其中包括吡啶基环化和芳基环化到吡啶上。Jones 6 公开了使用衍生自 3-溴吡啶的自由基，并将这种化学扩展到吡啶鎓自由基。7 然而，据我们所知，之前还没有报道过吡嗪基自由基环化。
• Pyridinium N-heteroarylaminides: a brief study on the synthesis and reactivity under solvent-free mechanochem conditions
  作者：Carolina Burgos、Marta Cordoba、Valentina Abet、Maria Moron、Rafael R. Castillo、M. Luisa Izquierdo

  DOI：10.3998/ark.5550190.0012.312

  日期：——

  The first example of a heterocyclic aromatic substitution by an N-ylide and the first examples of heteroaromatic halogenations in the presence of N-halosuccinimides using mechanochemical conditions are described.

  描述了在 N-卤代琥珀酰亚胺存在下使用机械化学条件进行杂环芳族取​​代的第一个实例和杂芳族卤化的第一个实例。
• An easy preparation of pyridinium N-heteroarylaminides
  作者：M José Reyes、Carolina Burgos、M Luisa Izquierdo、Julio Alvarez-Builla

  DOI：10.1016/j.tet.2003.11.076

  日期：2004.1

  Differently substituted pyridinium N-heteroarylaminides have been prepared in one step with good yield from N-aminopyridinium iodide and the corresponding heteroaryl chloride. (C) 2003 Elsevier Ltd. All rights reserved.