N-[5-(4-methylphenyl)pyridin-2-yl]pyridin-1-ium-1-aminide | 808750-47-2

• 英文名称: N-[5-(4-methylphenyl)pyridin-2-yl]pyridin-1-ium-1-aminide
• 英文别名: N-[5-(4-methylphenyl)pyridin-2-yl]pyridinium aminide
• CAS: 808750-47-2
• 化学式: C₁₇H₁₅N₃
• 分子量: 261.326
• InChiKey: RREQJTUTEWPMFB-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-[5-(4-methylphenyl)pyridin-2-yl]pyridin-1-ium-1-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89%的产率得到N-[(3'-bromo-5'-(4''-methylphenyl))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-甲苯硼酸 、 pyridinium N-(5'-bromopyridin-2'-yl)aminide 在 四(三苯基膦)钯 caesium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 8.0h， 以88%的产率得到N-[5-(4-methylphenyl)pyridin-2-yl]pyridin-1-ium-1-aminide
  参考文献：
  名称：

  Suzuki reaction on pyridinium N-(5-bromoheteroar-2-yl)aminides

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2004.09.136

文献信息

• 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 facile synthesis of 3,5-halo and aryl 1H-pyridin-2-ones from pyridinium N-(pyridin-2-yl)aminide
  作者：Fabiana Filace、David Sucunza、M. Luisa Izquierdo、Carolina Burgos、Julio Alvarez-Builla

  DOI：10.1016/j.tet.2013.05.065

  日期：2013.7

  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.