N-(pyrimidin-2'-yl)pyridinium aminide | 157020-16-1

• 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: N-(pyrimidin-2'-yl)pyridinium aminide
• 英文别名: N-(pyrimidin-2-yl)pyridinium aminide；pyridinium N-(2'-pyrimidinyl)aminide；Pyridin-1-ium-1-yl(pyrimidin-2-yl)azanide
• CAS: 157020-16-1
• 化学式: C₉H₈N₄
• 分子量: 172.189
• InChiKey: CXRJLIUZQBVVKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：

  4-甲基苄溴 、 N-(pyrimidin-2'-yl)pyridinium aminide 以 丙酮 为溶剂， 反应 36.0h， 以76%的产率得到N-(4-甲基苄基)-(2-嘧啶基)胺
  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
• 作为产物：
  描述：

  N-(2'-pyrimidinylamino)pyridinium bromide hydrobromide 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以97%的产率得到N-(pyrimidin-2'-yl)pyridinium aminide
  参考文献：
  名称：

  Azinium-N-（2'-azinyl）aminides：合成，结构与反应活性

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(01)90411-9

文献信息

• 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.
• New approaches to the synthesis of pyridinium N-heteroarylaminides
  作者：Marta Córdoba、M. Luisa Izquierdo、Julio Alvarez-Builla

  DOI：10.1016/j.tet.2008.06.024

  日期：2008.8

  Different substituted pyridinium N-heteroarylaminides have been prepared in one step from N-aminopyridinium iodide and the Corresponding heteroaryl halide by two alternative routes. The use of Pd catalysis allowed the easy preparation of products from the less reactive haloheterocycles. The use of water as a solvent in conjunction with microwave heating dramatically diminishes the reaction time without having an adverse effect on reaction yields. (C) 2008 Elsevier Ltd. All rights reserved.
• A Direct Route into Fused Imidazo-diazines and Imidazo-pyridines Using Nucleophilic Nitrenoids in a Gold-Catalyzed Formal [3 + 2]-Dipolar Cycloaddition
  作者：Miguel Garzón、Paul W. Davies

  DOI：10.1021/ol502346d

  日期：2014.9.19

  Pyridinium N-(heteroaryl)aminides can be employed as robust and practical synthetic equivalents of nucleophilic 1,3-N,N-dipoles in a formal cycloaddition onto electron-rich alkynes under gold catalysis. Convergent and regioselective access to five types of imidazo-fused heteroaromatics is provided from the appropriate aminide. The efficient transformation accommodates significant structural variation around the aminide, ynamide, or indolyl-alkyne reactants and tolerates sensitive functional groups.
• 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。
• Pyridinium N-(2′-Azinyl)Aminides: Regioselective Synthesis of 2-Alkylaminoazines
  作者：Valentı́n Martı́nez-Barrasa、Francisca Delgado、Carolina Burgos、J. Luis Garcı́a-Navı́o、M. Luisa Izquierdo、Julio Alvarez-Builla

  DOI：10.1016/s0040-4020(00)00084-3

  日期：2000.4

  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.