6-phenyl-3-(2-pyridyl)-1,2,4-triazine-5-carbonitrile | 453556-96-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 6-phenyl-3-(2-pyridyl)-1,2,4-triazine-5-carbonitrile
• 英文别名: 1,2,4-Triazine-5-carbonitrile, 6-phenyl-3-(2-pyridinyl)-；6-phenyl-3-pyridin-2-yl-1,2,4-triazine-5-carbonitrile
• CAS: 453556-96-2
• 化学式: C₁₅H₉N₅
• 分子量: 259.27
• InChiKey: RZWVYELQVXGBLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-phenyl-3-(2-pyridyl)-1,2,4-triazine-5-carbonitrile 在 盐酸 、 sodium tetrahydroborate 、 氯化亚砜 、 硫酸 作用下， 以 乙醇 、 苯 为溶剂， 反应 27.5h， 生成 6-hydroxymethyl-5-phenyl-2-(2'-pyridyl)-3,4-cyclopentenopyridine
  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
• 作为产物：
  描述：

  在 苯甲酸 、 亚硝酸异戊酯 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 1.5h， 以30%的产率得到6-phenyl-3-(2-pyridyl)-1,2,4-triazine-5-carbonitrile
  参考文献：
  名称：

  5-苯酰基-1,2,4-三嗪与1,2-脱氢苯在亚硝酸烷基酯存在下反应制备1-(2-吡啶基)异喹啉-3-腈的高效无氰方法

  摘要：

  开发了一种用于制备 1-(2-pyridyl)isoquinoline-3-carbonitriles (3-cyanoisoquinolines) 的无氰化物方法。5-phenacyl-3-(2-pyridyl)-1,2,4-triazines 与由邻氨基苯甲酸和过量亚硝酸戊酯原位生成的 1,2-脱氢苯相互作用，以良好的产率得到目标化合物。所提出的机制涉及在亚硝酸烷基酯的作用下 5-苯酰基基团原位转化为 5-氰基基团，以及由此形成的 5-氰基-1,2,4- 的逆向需求 aza-Diels-Alder 反应三嗪与 1,2-脱氢苯反应得到目标产物。5-苯甲酰基取代基的存在是反应的关键，如在 5-苯乙烯基-或 5-苯基乙炔基-3-(2-吡啶基)-1,2,4-三嗪的情况下，1,2观察到,4-三嗪环转化产物

  DOI：

  10.1055/s-0036-1590961

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-Acylmethyl-3-(2-pyridyl)-1,2,4-triazines: Synthesis and Complexes with Cu(II)
  作者：A. M. Prokhorov、D. N. Kozhevnikov、V. L. Rusinov、A. I. Matern、M. M. Nikitin、O. N. Chupakhin、I. L. Eremenko、G. G. Aleksandrov

  DOI：10.1007/s11178-006-0022-z

  日期：2005.11

  5-Acylmethyl-3-(2-pyridyl)-1,2,4-triazines are easily prepared from accessible 3-(2-pyridyl)-1,2,4-triazine 4-oxides by reaction of the latter with acetophenone or trifluoroacetone in the presence of NaH. The compounds obtained behaved as efficient ligands in reaction with CuCl2 furnishing dimeric neutral complexes with Cu(II) whose structure was investigated by means of X-ray diffraction analysis.

  5-乙酰甲基-3-(2-吡啶基)-1,2,4-三嗪类化合物通过可获得的3-(2-吡啶基)-1,2,4-三嗪4-氧化物与乙酰苯或三氟乙酰丙酮在NaH存在下的反应轻松制备。所得到的化合物作为高效配体与CuCl2反应，生成具有Cu(II)的二聚中性配合物，其结构通过X射线衍射分析进行了研究。
• Carborane-Functionalized Polyaza Aromatic Ligands:  Synthesis, Crystal Structure, and a Copper(II) Complex
  作者：Anton M. Prokhorov、Dmitry N. Kozhevnikov、Vladimir L. Rusinov、Oleg N. Chupakhin、Ivan V. Glukhov、Mikhail Yu. Antipin、Olga N. Kazheva、Anatolii N. Chekhlov、Oleg A. Dyachenko

  DOI：10.1021/om051058v

  日期：2006.6.1

  A consecutive aromatic nucleophilic substitutions of hydrogen in 1,2,4-triazine 4-oxides and an aza Diels−Alder reaction is a versatile route to carborane-functionalized bi- and terpyridines and their 1,2,4-triazine analogues. The heterocycles facilitate deboronation of the substituted carboranes, and the carborane moiety has a significant influence on the coordination properties of the ligands as

  在1,2,4-三嗪4-氧化物和aza Diels-Alder反应中进行的连续氢亲核取代反应是通向碳硼烷官能化的联吡啶和三联吡啶及其1,2,4-三嗪类似物的通用途径。杂环促进取代的碳硼烷的脱硼，并且碳硼烷部分也对配体的配位性质具有重要影响。
• 2-Aminooxazoles as novel dienophiles in the inverse demand Diels–Alder reaction with 1,2,4-triazines
  作者：Alexey P. Krinochkin、Guda Mallikarjuna Reddy、Dmitry S. Kopchuk、Pavel A. Slepukhin、Yaroslav K. Shtaitz、Igor A. Khalymbadzha、Igor S. Kovalev、Grigory A. Kim、Ilya N. Ganebnykh、Grigory V. Zyryanov、Oleg N. Chupakhin、Valery N. Charushin

  DOI：10.1016/j.mencom.2021.07.035

  日期：2021.7

  of 6-aryl-5-cyano-3-(pyridin-2-yl)-1,2,4-triazines with 2-amino-4-aryloxazoles proceeds as the inverse demand Diels–Alder reaction between the oxazole moiety as dienophile and the 1,2,4-triazine moiety as diene to construct new 4,5-diaryl-6-cyano-3-hydroxypyridin-2-yl fragment. A reaction mechanism is proposed, and the structure of the key-product is proved by the X-ray diffraction analysis.

  6-芳基-5-氰基-3-(吡啶-2-基)-1,2,4-三嗪与2-氨基-4-芳基恶唑的高温偶联随着恶唑部分之间的逆向狄尔斯-阿尔德反应而进行作为亲二烯体和 1,2,4-三嗪部分作为二烯构建新的 4,5-diaryl-6-cyano-3-hydroxypyridin-2-yl 片段。提出了反应机理，并通过X射线衍射分析证明了关键产物的结构。
• A facile synthesis of triazine integrated antipyrine derivatives through ecofriendly approach
  作者：Aluru Rammohan、Guda Mallikarjuna Reddy、Alexey P. Krinochkin、Dmitry S. Kopchuk、Maria I. Savchuk、Yaroslav K. Shtaitz、Grigory V. Zyryanov、Vladimir L. Rusinov、Oleg N. Chupakhin

  DOI：10.1080/00397911.2020.1823993

  日期：2021.1.17

  The present study describes a facile and solvent free synthesis of 1,2,4-triazine antipyrine derivatives (2a–f) in prominent yields (70–85%) over nucleophilic substitution of 5-carbonitrile triazin...

  本研究描述了 1,2,4-三嗪安替比林衍生物 (2a-f) 的简便且无溶剂合成，通过 5-腈三嗪的亲核取代，产率显着（70-85%）。