N-[3-bromo-5-(phenyl)pyridin-2-yl]pyridin-1-ium-1-aminide | 910791-85-4

• 英文名称: N-[3-bromo-5-(phenyl)pyridin-2-yl]pyridin-1-ium-1-aminide
• 英文别名: N-(3-bromo-5-phenylpyridin-2-yl)pyridinium aminide
• CAS: 910791-85-4
• 化学式: C₁₆H₁₂BrN₃
• 分子量: 326.195
• InChiKey: ZBJZEAIHILESPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  N-[3-bromo-5-(phenyl)pyridin-2-yl]pyridin-1-ium-1-aminide 在 吡啶 、 甲酸 、 硫酸 、 platinum on carbon 、 三乙胺 、 sodium nitrite 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 生成 3-bromo-5-phenylpyridin-2(1H)-one
  参考文献：
  名称：

  A facile synthesis of 3,5-halo and aryl 1H-pyridin-2-ones from pyridinium N-(pyridin-2-yl)aminide

  摘要：

  The synthesis of halogenated and arylated 1H-pyridin-2-ones starting from pyridinium N-(pyridin-2-yl)aminides is described. The synthetic pathway involves the reaction of pyridinium N-(5-bromopyridin-2-yl)aminide, N-(3-bromo-5-chloropyridin-2-yl)aminide or N-(3,5-dibromopyridin-2-yl)aminide with different boronic acids to afford monosubstituted and disubstituted aminides in good yields. An additional bromination in the 3-position of N-(5-arylpyridin-2-yl)aminides was performed. Finally, reduction of the N-N bond followed by the reaction of the corresponding 2-aminopyridines with sodium nitrite/sulfuric acid in water yields 3,5-disubstituted 1H-pyridin-2-ones in good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.065
• 作为产物：
  描述：

  pyridinium N-(5'-bromopyridin-2'-yl)aminide 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 15.0h， 生成 N-[3-bromo-5-(phenyl)pyridin-2-yl]pyridin-1-ium-1-aminide
  参考文献：
  名称：

  A facile synthesis of 3,5-halo and aryl 1H-pyridin-2-ones from pyridinium N-(pyridin-2-yl)aminide

  摘要：

  The synthesis of halogenated and arylated 1H-pyridin-2-ones starting from pyridinium N-(pyridin-2-yl)aminides is described. The synthetic pathway involves the reaction of pyridinium N-(5-bromopyridin-2-yl)aminide, N-(3-bromo-5-chloropyridin-2-yl)aminide or N-(3,5-dibromopyridin-2-yl)aminide with different boronic acids to afford monosubstituted and disubstituted aminides in good yields. An additional bromination in the 3-position of N-(5-arylpyridin-2-yl)aminides was performed. Finally, reduction of the N-N bond followed by the reaction of the corresponding 2-aminopyridines with sodium nitrite/sulfuric acid in water yields 3,5-disubstituted 1H-pyridin-2-ones in good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.065

文献信息

• A New Class of Pyrazolopyridine Nucleus with Fluorescent Properties, Obtained through Either a Radical or a Pd Arylation Pathway from <i>N</i>-Azinylpyridinium <i>N</i>-Aminides
  作者：Valentina Abet、Araceli Nuñez、Francisco Mendicuti、Carolina Burgos、Julio Alvarez-Builla

  DOI：10.1021/jo801549u

  日期：2008.11.21

  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.
• Pd-catalyzed reactions on pyridinium N-heteroarylaminides. Step-by-step synthesis of 3,5-unsymmetrically disubstituted 2-aminopyridines
  作者：Marta Córdoba、Rafael R. Castillo、M. Luisa Izquierdo、Julio Alvarez-Builla

  DOI：10.1016/j.tet.2010.02.036

  日期：2010.4

  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
• Regioselective Suzuki coupling on pyridinium N-(3,5-dibromoheteroar-2-yl)aminides
  作者：M. José Reyes、Rafael Castillo、M. Luisa Izquierdo、Julio Alvarez-Builla

  DOI：10.1016/j.tetlet.2006.06.097

  日期：2006.9

  A regioselective Suzuki-Miyaura cross-coupling reaction on 3',5'-dibromo pyridinium N-(2'-azinyl)aminides is reported. A series of 3'-aryl(or heteroaryl)-5-bromo-pyridinium N-(2'-pirazinyl)aminides were obtained in good yields. Two isomeric 3',5'-diaryl pyridinium N-(2-azinyl)aminides were also prepared. (c) 2006 Elsevier Ltd. All rights reserved.