N-(3',5'-dibromopyrazin-2'-yl)pyridinium aminide | 475641-51-1

• 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-(3',5'-dibromopyrazin-2'-yl)pyridinium aminide
• 英文别名: (3,5-Dibromopyrazin-2-yl)-pyridin-1-ium-1-ylazanide
• CAS: 475641-51-1
• 化学式: C₉H₆Br₂N₄
• 分子量: 329.981
• InChiKey: QCBNWKWIHZKXPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 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：

  N-(3',5'-dibromopyrazin-2'-yl)pyridinium aminide 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 3.0h， 生成 N-[3'-phenyl-5'-(3''-pyridyl)pyraz-2'-yl]pyridinium aminide
  参考文献：
  名称：

  Regioselective Suzuki coupling on pyridinium N-(3,5-dibromoheteroar-2-yl)aminides

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2006.06.097
• 作为产物：
  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

文献信息

• 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。
• 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.
• 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.
• 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.