pyridinium N-(5'-bromopyridin-2'-yl)aminide | 157020-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: pyridinium N-(5'-bromopyridin-2'-yl)aminide
• 英文别名: pyridinium N-(5'-bromo-2'-pyridyl)aminide；pyridinium N-<2'-(5'-bromopyridyl)>aminide；N-(5-bromopyridin-2-yl)pyridinium aminide；N-(5-bromopyridin-2-yl)pyridin-1-ium-1-aminide；N-(5-bromopyridin-2-yl)(pyridinium)amide；(5-Bromopyridin-2-yl)-pyridin-1-ium-1-ylazanide
• CAS: 157020-26-3
• 化学式: C₁₀H₈BrN₃
• 分子量: 250.098
• InChiKey: ZBZDWTWKGFKDGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 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：
  17.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  pyridinium N-(5'-bromopyridin-2'-yl)aminide 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以85%的产率得到N-(3',5'-dibromopyrid-2'-yl)pyridinium aminide
  参考文献：
  名称：

  Halogenation of pyridinium-N-(2′-pyridyl)aminide: An easy synthesis of halo-2-aminopyridines

  摘要：

  The regioselective halogenation of pyridinium-N-(2'-pyridyl)aminide 1 with N-chloro, bromo or iodosuccinimide under mild conditions is described. The method, combined with a reduction of the N-N bond, allows an easy preparation of 5-halo and 3,5-dihalo-2-aminopyridines 4.

  DOI：

  10.1016/0040-4020(95)00478-q
• 作为产物：
  描述：

  pyridinium N-(2'-pyridyl)aminide 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以71%的产率得到pyridinium N-(5'-bromopyridin-2'-yl)aminide
  参考文献：
  名称：

  Halogenation of pyridinium-N-(2′-pyridyl)aminide: An easy synthesis of halo-2-aminopyridines

  摘要：

  The regioselective halogenation of pyridinium-N-(2'-pyridyl)aminide 1 with N-chloro, bromo or iodosuccinimide under mild conditions is described. The method, combined with a reduction of the N-N bond, allows an easy preparation of 5-halo and 3,5-dihalo-2-aminopyridines 4.

  DOI：

  10.1016/0040-4020(95)00478-q

文献信息

• Pyridinium N-(2′-azinyl)aminides: regioselective synthesis of N-(2-pyridyl) substituted polyamines
  作者：M José Reyes、Francisca Delgado、M Luisa Izquierdo、Julio Alvarez-Builla

  DOI：10.1016/s0040-4020(02)00901-8

  日期：2002.10

  The regioselective alkylation of pyridinium-N-(2′-pyridyl)aminide with alkyl dihalides under mild conditions, followed by N–N bond reduction of the corresponding bis-salts, allowed an easy preparation of N,N′-bis(2-pyridyl)diamines. The same methodology has been applied to the synthesis of N,N′,N″-tris(2-pyridyl)triamines.

  的吡啶鎓区域选择性烷基化ñ - （2'-吡啶基）aminide与温和的条件下烷基二卤化物，随后加入N-N键还原相应的二盐的，允许一个简单的制剂的Ñ，Ñ N'-双（2-吡啶基）二胺。相同的方法已应用于N，N '，N '' -三（2-吡啶基）三胺的合成。
• 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-pyridyl)aminides: A selective approach to substituted 2-aminopyridines
  作者：Rosa Carceller、Jose L. García-Navío、María L. Izquierdo、Julio Alvarez-Builla

  DOI：10.1016/s0040-4039(00)91991-9

  日期：1993.3

  Differently substituted 2-aminopyridines have been prepared in two steps from pyridinium-N-(2-pyridyl)aminide, by reaction with the corresponding elect

  分两步从吡啶鎓-N-（2-吡啶基）氨基化物制备二取代的2-氨基吡啶，方法是与相应的
• 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.
• Sonogashira reaction on pyridinium N-heteroarylaminides
  作者：Marta Córdoba、M. Luisa Izquierdo、Julio Alvarez-Builla

  DOI：10.1016/j.tetlet.2011.01.121

  日期：2011.4

  The reactivity of N-(5-iodopyridin-2-yl)aminide in a copper-free Sonogashira cross-coupling process is reported. The reaction proceeds on using PdCl2(PPh3)(2) and DABCO as the base under microwave irradiation in acetonitrile or water as solvents. The process can also be carried out by traditional heating in acetonitrile on using Pd(AcO)(2)/DABCO with Cs2CO3. (C) 2011 Elsevier Ltd. All rights reserved.