6-(4-methylphenyl)-3-(2-pyridyl)-1,2,4-triazine 4-oxide | 517876-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(4-methylphenyl)-3-(2-pyridyl)-1,2,4-triazine 4-oxide
• 英文别名: 6-(4-Methylphenyl)-4-oxido-3-pyridin-2-yl-1,2,4-triazin-4-ium
• CAS: 517876-16-3
• 化学式: C₁₅H₁₂N₄O
• 分子量: 264.286
• InChiKey: RNCUKCQWCKXVNE-UHFFFAOYSA-N

物化性质

• 沸点：
  526.6±42.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(4-methylphenyl)-3-(2-pyridyl)-1,2,4-triazine 4-oxide 以 二氯甲烷 、 甲苯 为溶剂， 反应 7.5h， 生成 6-cyano-5-(4-methylphenyl)-2,2'-bipyridine
  参考文献：
  名称：

  Luminescent neutral lanthanide complexes of 5-aryl-2,2′-bipyridine-6-carboxylic acids, synthesis and properties

  摘要：

  Luminescent lanthanide complexes of 4-aryl-1-(2-pyridyl)-6,7-dihydro-5H-cyclopenta[c]pyridine-3-carboxylic acids and 5-toly1-2,2'-bipyridine-6-carboxylic acid were prepared. The ligands were synthesized using the "1,2,4-triazine" methodology. In one case, the opportunity of copper complex preparation, followed by exchange of the metal cation from copper to europium to overcome synthetic difficulties, was demonstrated. The ability of tuning the properties of the complexes by means of varying the structure of the ligands was demonstrated. In particular, the introduction of the cyclopentene moiety allowed the preparation of highly soluble complexes in non-polar organic solvents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.09.055
• 作为产物：
  描述：

  4-methyl-α-oximinoacetophenone hydrazone 在 lead(II,IV) oxide 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 6-(4-methylphenyl)-3-(2-pyridyl)-1,2,4-triazine 4-oxide
  参考文献：
  名称：

  A Versatile Strategy for the Synthesis of Functionalized 2,2‘-Bi- and 2,2‘:6‘,2‘ ‘-Terpyridines via Their 1,2,4-Triazine Analogues

  摘要：

  A general synthetic route for the synthesis of functionalized bi- and terpyridines is reported. Functionalized 1,2,4-triazene 4-oxides 7 and 8-obtained from the reaction of hydrazones 1 with pyridine aldehydes and followed by oxidation-are functionalized by introduction of a cyano group via nucleophilic aromatic substitution. The thus-obtained 5-cyano-1,2,4-triazines 9 and 10 undergo facile inverse-electron-demand Diels-Alder reactions with enamines and alkenes to yield functionalized bi- and terpyridines, respectively. The substituent at position 6 of the 1,2,4-triazene 4-oxides must be aromatic or heteroaromatic in order to allow their facile synthesis, but other substituents and reagents may vary. Each step of the synthetic route allows diversification, which makes the approach particularly useful for the facile synthesis of a large variety of functionalized bi- and terpyridines.

  DOI：

  10.1021/jo0267955

文献信息

• Studies on the interactions of 5-<i>R</i>-3-(2-pyridyl)-1,2,4-triazines with arynes: inverse demand aza-Diels–Alder reaction <i>versus</i> aryne-mediated domino process
  作者：Dmitry S. Kopchuk、Igor L. Nikonov、Albert F. Khasanov、Kousik Giri、Sougata Santra、Igor S. Kovalev、Emiliya V. Nosova、Sravya Gundala、Padmavathi Venkatapuram、Grigory V. Zyryanov、Adinath Majee、Oleg N. Chupakhin

  DOI：10.1039/c8ob00847g

  日期：——

  aza-Diels–Alder products or 1,2,4-triazine ring rearrangement (domino) products as major ones depending on the nature of both the substituents at the C5 position of the 1,2,4-triazine core or in the aryne moiety. The structures of the key products were confirmed based on X-ray data. Based on the density functional theoretical (DFT) studies of the Diels–Alder transition state geometries, the influence of the nature

  已经研究了取代的5 - R -3-（吡啶基-2）-1,2,4-三嗪与原位生成的取代的芳烃中间体之间的相互作用。根据1,2,5碳原子上两个取代基的性质，反应可提供反需求（ID）的aza-Diels-Alder产品或1,2,4-三嗪环重排（domino）产品作为主要产品。 4-三嗪核或在芳烃部分。根据X射线数据确定了关键产品的结构。基于Diels–Alder过渡态几何的密度泛函理论（DFT）研究，提出了芳烃性质对1,2,4-三嗪转化方向的影响。
• 5-Aryl-6-arylthio-2,2′-bipyridine and 6-Arylthio-2,5-diarylpyridine Fluorophores: Pot, Atom, Step Economic (PASE) Synthesis and Photophysical Studies
  作者：Maria I. Savchuk、Dmitry S. Kopchuk、Olga S. Taniya、Igor L. Nikonov、Ilya N. Egorov、Sougata Santra、Grigory V. Zyryanov、Oleg N. Chupakhin、Valery N. Charushin

  DOI：10.1007/s10895-021-02714-3

  日期：2021.7

  for the synthesis of C6-thiophenol-substituted (2,2′-bi)pyridines as it is well known that thio-substituted (bi)pyridines and their aza-analogs are of wide practical interest. The photophysical properties of the obtained compounds are studied and compared with those reported earlier for 6-substituted 2,2′-bipyridines. The influence of the nature of substituents in the 6-arylthio(bi)pyridine core on

  通过S N H在6中报道了一种PASE（锅，步，原子，经济）合成5-芳基-6-芳硫基-2,2'-联吡啶和6-芳硫基-2,5-二芳基吡啶配体/荧光团的方法。 -芳基-5 H -1,2,4-三嗪/氮杂-Diels-Alder反应序列。在本文中，“ 1,2,4-三嗪”方法已成功用于合成C6-硫酚取代的（2,2'-bi）吡啶，因为众所周知，硫取代的（bi）吡啶和他们的氮杂-模拟具有广泛的实际意义。研究了所得化合物的光物理性质，并将其与先前报道的6-取代的2,2'-联吡啶的光物理性质进行了比较。讨论了6-芳硫基（bi）吡啶核中取代基的性质对光物理性质的影响。观察到，新化合物表现出有希望的光物理性质，可以被认为是潜在的推挽式荧光团。此外，与先前描述的6- H相比，它们显示出更大的斯托克斯位移值，与五氟苯基取代的2,2'-联吡啶相比，6-芳基氨基和6-五氟-2,2'-联吡啶和更高的荧光量子产率值。取决于
• Consecutive nucleophilic substitution and aza Diels–Alder reaction—an efficient strategy to functionalized 2,2′-bipyridines
  作者：Dmitry N. Kozhevnikov、Valery N. Kozhevnikov、Anton M. Prokhorov、Maria M. Ustinova、Vladimir L. Rusinov、Oleg N. Chupakhin、Grigory G. Aleksandrov、Burkhard König

  DOI：10.1016/j.tetlet.2005.12.006

  日期：2006.2

  An efficient strategy for the synthesis of functionalized 2,2'-bipyridines is reported. The strategy is based on readily available 3-pyridyl-1,2,4-triazine 4-oxides and uses a reaction sequence of nucleophilic substitution of hydrogen and aza Diels-Alder reaction. (c) 2005 Elsevier Ltd. All rights reserved.
• Direct introduction of acetylene moieties into azines by methodology
  作者：Anton M. Prokhorov、Mieczysław Mąkosza、Oleg N. Chupakhin

  DOI：10.1016/j.tetlet.2009.01.070

  日期：2009.4

  The N-oxides of azines 1a-g react with lithium and/or potassium acetylides to give the corresponding ethynylazines 2a-g. Reaction with lithium acetylide requires subsequent acylation of the intermediate anionic adduct for rearomatization whereas in the case of potassium acetylide, auto-aromatization takes place. (C) 2009 Published by Elsevier Ltd.
• Luminescent neutral lanthanide complexes of 5-aryl-2,2′-bipyridine-6-carboxylic acids, synthesis and properties
  作者：Alexey P. Krinochkin、Dmitry S. Kopchuk、Dmitry N. Kozhevnikov

  DOI：10.1016/j.poly.2015.09.055

  日期：2015.12

  Luminescent lanthanide complexes of 4-aryl-1-(2-pyridyl)-6,7-dihydro-5H-cyclopenta[c]pyridine-3-carboxylic acids and 5-toly1-2,2'-bipyridine-6-carboxylic acid were prepared. The ligands were synthesized using the "1,2,4-triazine" methodology. In one case, the opportunity of copper complex preparation, followed by exchange of the metal cation from copper to europium to overcome synthetic difficulties, was demonstrated. The ability of tuning the properties of the complexes by means of varying the structure of the ligands was demonstrated. In particular, the introduction of the cyclopentene moiety allowed the preparation of highly soluble complexes in non-polar organic solvents. (C) 2015 Elsevier Ltd. All rights reserved.