3-(pyridin-2-yl)-[1,2,4]triazolo[4,3-a]pyridine | 5006-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(pyridin-2-yl)-[1,2,4]triazolo[4,3-a]pyridine
• 英文别名: 3-(2-pyridyl)[1,2,4]triazolo[4,3-a]pyridine；3-(Pyrid-2-yl)-s-triazolo<4,3-a>pyridin；3-Pyridin-2-yl-[1,2,4]triazolo[4,3-a]pyridine
• CAS: 5006-54-2
• 化学式: C₁₁H₈N₄
• 分子量: 196.211
• InChiKey: XDDFMBJBQGJWBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 3-(pyridin-2-yl)-[1,2,4]triazolo[4,3-a]pyridine 以 乙腈 、 苯 为溶剂， 以81%的产率得到fac-[Re(I) (CO)3 (triazolopyridine) (chloride)]
  参考文献：
  名称：

  Synthesis and structure of luminescent ReI(CO)3Cl complexes incorporating pyridyltriazine, pyrazinyltriazine and triazolopyridine chelation

  摘要：

  The triazine and triazolo ligands (general abbreviations, L) used in the present work are pyridyltriazine (L-1), pyrazinyltriazine (L-2) and triazolopyridine (L-3), respectively. The reaction of Re(CO)(5)Cl with a slight excess of L in boiling benzene has furnished complexes of the type Re(CO)(3)Cl(L). In dichloromethane solution the complexes display a band of moderate intensity in the visible region: Re-I (CO)(3)Cl(L-1), 433 nm; Re-I(CO)(3)Cl(L-2) 451 nm and Re-I(CO)(3)(L-3) 440 nm. This band is tentatively assigned to a pi(Re) --> pi*(L) MLCT excitation. The solutions are also fluorescent, the emission peaks lying at 679, 671 and 592 nm, respectively. The fluorescence is believed to originate from the (MLCT)-M-3 state. The quantum yield in the three cases are 5.6 x 10(-4), 5.5 x 10(-4) and 0.036, respectively. Interestingly the L 3 complex is comparable with Ru(bpy)(3)(2+) with regard to quantum yield. The IR and H-1 NMR spectra of the chelates are reported. The complexes are electroactive in acetonitrile solution wherein an irreversible one-electron anodic oxidation (1.30-1.50 V) is observed cyclic voltammetrically. The X-ray structures of the L-1 and L-3 complexes have been determined revealing distorted octahedral ReC3N2Cl coordination spheres. The carbon monoxide ligands are facially disposed. In both complexes the chelate rings make a satisfactory plane (mean deviation 0.03 angstrom). The average Re-N, Re-C and Re-Cl lengths are unexceptional. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2006.01.028
• 作为产物：
  描述：

  Z-pyridine-2-carbaldehyde 2'-pyridylhydrazone 在 mercury(II) diacetate 作用下， 以 氘代二甲亚砜 为溶剂， 反应 504.0h， 生成 3-(pyridin-2-yl)-[1,2,4]triazolo[4,3-a]pyridine
  参考文献：
  名称：

  Butler, Richard N.; Johnston, Sean M., Journal of the Chemical Society. Perkin transactions I, 1984, p. 2109 - 2116

  摘要：

  DOI：

文献信息

• Electrochemical synthesis of 1,2,4-triazole-fused heterocycles
  作者：Zenghui Ye、Mingruo Ding、Yanqi Wu、Yong Li、Wenkai Hua、Fengzhi Zhang

  DOI：10.1039/c7gc03739b

  日期：——

  cross-coupling reaction has been developed under mild electrolytic conditions. In this atom- and step-economical one-pot process, valuable 1,2,4-triazolo[4,3-a]pyridines and related heterocyclic compounds could be synthesized efficiently from commercially available aliphatic or (hetero)aromatic aldehydes and 2-hydrazinopyridines. Various functional groups are compatible with this metal- and oxidant-free

  在温和的电解条件下已开发出无试剂的分子内脱氢C–N交叉偶联反应。在这种原子经济和一步经济的一锅法中，有价值的1,2,4-三唑并[4,3- a ]吡啶和相关的杂环化合物可以从可商购的脂族或（杂）芳族醛和2-肼基吡啶。各种官能团都与这种无金属和无氧化剂的方案兼容，可以轻松地以克为单位进行操作。这种新方法被应用于最畅销药物Xanax的合成和后期功能化，以在生物学相关的先导分子中产生化学多样性。
• A mild synthesis of [1,2,4]triazolo[4,3-a]pyridines
  作者：Michael A. Schmidt、Xinhua Qian

  DOI：10.1016/j.tetlet.2013.08.024

  日期：2013.10

  The reaction between 2-hydrazinopyridines and ethyl imidates was examined as a one-pot method for rapidly preparing [1,2,4]triazolo[4,3-a]pyridines. A diverse set of 2-hydrazinopyridines were cyclized with a variety of alkyl- and aryl-substituted ethyl imidates in good yields. The reaction proceeds optimally under mild conditions (50−70 °C) using 1.5 equiv of acetic acid. The electronic and steric

  作为快速制备[1,2,4]三唑并[4,3- a ]吡啶的一锅法，研究了2-肼基吡啶和酰亚胺乙酯之间的反应。用各种烷基取代基和芳基取代的乙基酰亚胺酯以高收率将各种不同的2-肼基吡啶环化。使用1.5当量的乙酸，在温和的条件下（50-70°C），反应可以最佳地进行。肼和亚氨酸酯的电子和位阻性质强烈影响反应速率。当使用高度缺乏电子的2-肼基吡啶时，产物重排为[1,2,4]三唑并[1,5- a ]吡啶。
• Portrait of a Family of Highly Stabilizing and Selective Guanine Quadruplex Platinum(II)‐Based Binders
  作者：Caitlin E. Miron、Mickey Chen、Jean‐Louis Mergny、Anne Petitjean

  DOI：10.1002/chem.202103839

  日期：2022.2

  The synthesis and biophysical screening of guanine quadruplex stabilization and binding properties of a family of platinum di-imine complexes are described. The second-generation binders display enhanced stabilization and selectivity compared to the parent compound, bearing much promise for the future evolution of this novel platform.

  描述了一系列铂二亚胺配合物的鸟嘌呤四链体稳定性和结合特性的合成和生物物理筛选。与母体化合物相比，第二代粘合剂显示出更高的稳定性和选择性，为这一新型平台的未来发展带来了很大希望。
• Oxidative C(sp³)–H functionalization of methyl-azaheteroarenes: a facile route to 1,2,4-triazolo[4,3-<i>a</i>]pyridines
  作者：Wei-Zhao Weng、Yin-He Gao、Xue Zhang、Yan-Hua Liu、Ying-Jie Shen、Yan-Ping Zhu、Yuan-Yuan Sun、Qing-Guo Meng、An-Xin Wu

  DOI：10.1039/c9ob00033j

  日期：——

  We herein describe an oxidative [4 + 1] annulation used to prepare 1,2,4-triazolo[4,3-a]pyridines in the presence of I2–DMSO. This protocol enables synthesis of triazolo[4,3-a]pyridine–quinoline linked diheterocycles via a direct oxidative functionalization of sp3 C–H bonds of 2-methyl-azaheteroarenes. The reaction shows a wide substrate scope and good functional group tolerance.

  我们在本文中描述了在I 2 -DMSO存在下用于制备1,2,4-三唑并[4,3- a ]吡啶的氧化[4 +1]环。该协议能够通过2-甲基-氮杂杂环芳烃的sp 3 C–H键的直接氧化功能合成三唑并[4，3 - a ]吡啶-喹啉连接的二杂环。该反应显示出较宽的底物范围和良好的官能团耐受性。
• Improved redox couple for electrochemical and optoelectronic devices
  申请人：Ecole Polytechnique Fédérale de Lausanne (EPFL)

  公开号：EP2492277A1

  公开（公告）日：2012-08-29

  The present invention provides an improved redox couple for electrochemical and optoelectronic devices. The redox couple is based on a complex of a first row transition metal, said complex containing at least one mono-, bi-, or tridentate ligand comprising a substituted or unsubstituted ring or ring system comprising a five-membered N-containing heteroring and/or a six-membered ring comprising at least two heteroatoms, at least one of which being a nitrogen atom, said five- or six-membered heteroring, respectively, comprising at least one double bond. The invention also relates to electrolytes and to the devices containing the complex, and to the use of the complex as a redox couple.

  本发明提供了一种改进的氧化还原偶对，用于电化学和光电子器件。该氧化还原偶对基于第一行过渡金属的配合物，所述配合物至少含有一个单、双或三齿配体，包括一个取代或未取代的环或环系统，其中包括一个五元N-含杂环和/或一个至少含有两个杂原子的六元环，其中至少一个是氮原子，所述的五元或六元杂环分别包括至少一个双键。该发明还涉及电解质、含有该配合物的器件，以及将该配合物用作氧化还原偶对的用途。