N-(5'-bromo-3'-phenylpyraz-2'-yl)pyridinium aminide | 910791-84-3

• 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-(5'-bromo-3'-phenylpyraz-2'-yl)pyridinium aminide
• 英文别名: N-(5-bromo-3-phenylpyrazin-2-yl)pyridinium aminide；(5-Bromo-3-phenylpyrazin-2-yl)-pyridin-1-ium-1-ylazanide
• CAS: 910791-84-3
• 化学式: C₁₅H₁₁BrN₄
• 分子量: 327.183
• InChiKey: CHEYIKLNOKLCRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• 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-(5'-bromo-3'-phenylpyraz-2'-yl)pyridinium aminide 、 苯并噻吩-3-硼酸 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89%的产率得到N-[5-(benzo[b]thiophen-3-yl)-3-phenylpyrazin-2-yl]pyridinium aminide
  参考文献：
  名称：

  Suzuki reaction on pyridinium N-haloheteroarylaminides: regioselective synthesis of 3,5-disubstituted 2-aminopyrazines

  摘要：

  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.

  DOI：

  10.1016/j.tet.2007.11.057
• 作为产物：
  描述：

  N-(3',5'-dibromopyrazin-2'-yl)pyridinium aminide 、 苯硼酸 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 3.0h， 以75%的产率得到N-(5'-bromo-3'-phenylpyraz-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

文献信息

• 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.
• 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.