N-[5-(4-methoxylphenyl)pyridin-2-yl]pyridinium aminide | 808750-49-4

• 英文名称: N-[5-(4-methoxylphenyl)pyridin-2-yl]pyridinium aminide
• 英文别名: N-[5-(4-methoxyphenyl)pyridin-2-yl]pyridinium aminide
• CAS: 808750-49-4
• 化学式: C₁₇H₁₅N₃O
• 分子量: 277.326
• InChiKey: QSRHJJMVTZOJKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 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：

  N-[5-(4-methoxylphenyl)pyridin-2-yl]pyridinium aminide 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以87%的产率得到N-[(3'-bromo-5'-(4''-methoxyphenyl))pyridin-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：

  4-甲氧基苯硼酸 、 pyridinium N-(5'-bromopyridin-2'-yl)aminide 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 8.0h， 以85%的产率得到N-[5-(4-methoxylphenyl)pyridin-2-yl]pyridinium aminide
  参考文献：
  名称：

  Pd-catalyzed reactions on pyridinium N-heteroarylaminides. Step-by-step synthesis of 3,5-unsymmetrically disubstituted 2-aminopyridines

  摘要：

  Suzuki-Miyaura cross-coupling processes on N-pyridinium bromoazinyl aminides allow access to 3,5-disubstituted N-alkyl-2-aminopyridines The synthetic pathway involves a regioselective brommation of pyridinum N-(pyridin-2-yl)aminide and a subsequent reaction with boronic acids to afford monosubstituted aminides in good yields An additional brommation in the 5-position of the pyridine ring followed by a coupling reaction gives pyridinium N-(3,5-diarylpyridin-2-yl)aminides Finally, a regioselective alkylation on the exo-nitrogen and reduction of the N-N bond yields highly substituted 2-aminopyridines (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.02.036

文献信息

• Suzuki reaction on pyridinium N-(5-bromoheteroar-2-yl)aminides
  作者：M. José Reyes、M. Luisa Izquierdo、Julio Alvarez-Builla

  DOI：10.1016/j.tetlet.2004.09.136

  日期：2004.11

  The reactivity of substituted pyridinium N-(2'-azinyl)aminides in Suzuki-Miyaura cross-coupling reaction is reported. The reaction proceeds in good yield employing Cs2CO3 as base, and producing substitution on the negatively charged moiety. (C) 2004 Published by Elsevier Ltd.
• Suzuki reaction on pyridinium N-haloheteroarylaminides: regioselective synthesis of 3,5-disubstituted 2-aminopyrazines
  作者：Rafael Castillo、M. José Reyes、M. Luisa Izquierdo、Julio Alvarez-Builla

  DOI：10.1016/j.tet.2007.11.057

  日期：2008.2

  An extensive study of Suzuki-Miyaura cross-coupling processes on N-pyridinium bromoazinyl aminides has been performed. Mono- and disubstitution on 5- and 3,5-bromo derivatives produced the corresponding aryl derivatives. In the disubstituted compounds regioselective substitution at the 3-position occurred, vicinal to the aminide nitrogen, and this was more evident in pyrazine derivatives. The commonly used strategy involving N-alkylation and reduction of the N-N bond gave rise to a series of 2-alkylamino-3,5-disubstituted-pyrazines. (c) 2007 Elsevier Ltd. All rights reserved.