2-(2H-indazol-2-yl)benzonitrile | 81265-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2H-indazol-2-yl)benzonitrile
• 英文别名: BENZONITRILE, o-(2H-INDAZOL-2-YL)-；2-indazol-2-ylbenzonitrile
• CAS: 81265-86-3
• 化学式: C₁₄H₉N₃
• 分子量: 219.246
• InChiKey: MKHLUYSLGRTLRE-UHFFFAOYSA-N

物化性质

• 沸点：
  312.6±34.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 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：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2H-indazol-2-yl)benzonitrile 在 potassium hydroxide 作用下， 以 叔丁醇 为溶剂， 反应 4.0h， 以67%的产率得到2-(2H-indazol-2-yl)benzamide
  参考文献：
  名称：

  Rh(III)-Catalyzed C–H Cyanation of 2H-Indazole with N-Cyano-N-phenyl-p-toluenesulfonamide

  摘要：

  A Rh(III)-catalyzed direct cyanation of 2H-indazoles with N-cyano-N-phenyl-p-toluenesulfonamide has been realized via a chelation-assisted strategy. The methodology enables regioselective access to various ortho-cyanated phenylindazoles in good yields with a broad substrate scope and good functional group compatibility. The obtained cyanated indazoles could further be converted into other value-added chemicals. Importantly, the current protocol is featured with several characteristics, including a novel cyanating agent, good regioselectivity, and operational convenience.

  DOI：

  10.1021/acs.joc.0c01386
• 作为产物：
  描述：

  2-(2-nitrobenzylamino)benzonitrile 以 甲醇 、 二氯甲烷 、 水 为溶剂， 以85%的产率得到2-(2H-indazol-2-yl)benzonitrile
  参考文献：
  名称：

  Synthesis and Electrochemical Behaviour of 2-N-Substituted Indazoles.

  摘要：

  A new 2-N-aryl-3-methoxycarbonylindazole synthesis from the 6 F mol(-1) reduction of appropriately substituted aryl-nitrones has been developed. The indazoles bearing an electron withdrawing group in the 2-position are electroreducible compounds at high negative potentials producing selectively the corresponding 2-N-substituted indazolines in aqueous alcoholic medium. The nitrile and ester groups are not reduced under the reaction conditions. Three new 2-N-aryl-indazolines were synthesized and characterized. A second electron withdrawing group attached at the 3-position leads to a less cathodic reduction of the 2-N-aryl-3-methoxycarbonylindazole. An appropriately substituted indazoline was used to generate ill situ a new tetracyclic heterocycle.

  DOI：

  10.3891/acta.chem.scand.53-0814

文献信息

• Synthesis, Antiprotozoal Activity, and Cheminformatic Analysis of 2-Phenyl-2H-Indazole Derivatives
  作者：Karen Rodríguez-Villar、Lilián Yépez-Mulia、Miguel Cortés-Gines、Jacobo David Aguilera-Perdomo、Edgar A. Quintana-Salazar、Kevin Samael Olascoaga Del Angel、Francisco Cortés-Benítez、Juan Francisco Palacios-Espinosa、Olivia Soria-Arteche、Jaime Pérez-Villanueva

  DOI：10.3390/molecules26082145

  日期：——

  antiprotozoals. The 2-phenyl-2H-indazole scaffold was accessed by a one-pot procedure, which includes a combination of ultrasound synthesis under neat conditions as well as Cadogan’s cyclization. Moreover, some compounds were derivatized to have an appropriate set to provide structure-activity relationships (SAR) information. Whereas the antiprotozoal activity of six of these compounds against E. histolytica,

  吲唑是药物化学中的重要支架。目前，合成方法学的进展已允许制备几种具有令人感兴趣的药理特性的新型吲唑衍生物。特别地，最近已经报道了吲唑衍生物的抗原生动物活性。在此，合成并研究了一系列22种吲唑衍生物作为抗原生动物。通过一锅法获得2-苯基-2 H-吲唑支架，该方法包括在纯净条件下超声合成以及Cadogan环化的组合。此外，某些化合物已衍生化为具有适当的一组化合物，以提供结构-活性关系（SAR）信息。而这些化合物中的六种对溶组织性大肠杆菌的抗原生动物活性，G。intestinalis和T.vaginalis先前已有报道，另外16种化合物的活性针对这些相同的原生动物进行了评估。生物学测定揭示了有利于对所测试的三种原生动物的抗原生动物活性的结构特征，例如2-苯基环上的吸电子基团。值得一提的是，吲唑衍生物具有很强的抗原生动物活性，并且具有连续SAR的特征。
• A General One-Pot Synthesis of 2<i>H</i> -Indazoles Using an Organophosphorus-Silane System
  作者：Jens Schoene、Hassen Bel Abed、Peter Schmieder、Mathias Christmann、Marc Nazaré

  DOI：10.1002/chem.201800763

  日期：2018.6.26

  A simple and direct approach for the regioselective construction of the privileged 2H‐indazole scaffold is described. The developed one‐pot strategy involves phospholene‐mediated N−N bond formation to access 2H‐indazoles. The amount of organophosphorus reagent was minimized by recycling the phospholene oxide with organosilane reductants. Starting from functionalized 2‐nitrobenzaldehydes and primary

  描述了一种简单而直接的方法来进行特权2 H-吲唑支架的区域选择性构建。发达的一锅策略涉及通过磷烯介导的N-N键的形成来获得2 H-吲唑。通过使磷烯氧化物与有机硅烷还原剂一起循环使用，可最大程度地减少有机磷试剂的用量。从官能化的2-硝基苯甲醛和伯胺开始，温和的还原环化（包括使用市售的磷烯氧化物和硅烷）可提供各种取代的2 H-吲唑，收率良好至优异。
• Gold Modified Zeolite: An Efficient Heterogeneous Catalyst for &lt;I&gt;N&lt;/I&gt;-Arylation of Indazole
  作者：P Emayavaramban、K Kadirvelu、N Dharmaraj

  DOI：10.1166/jnn.2016.12905

  日期：2016.9.1

  We herein report N-arylation of indazole with aryl halides using gold modified zeolites (Au-zeolites) as an efficient catalytic system. Au-zeolites with three different gold loading were prepared by ion-exchange method and characterized by UV-visible diffuse reflectance spectroscopy (UV-DRS), transmission electron microscopy and energy-dispersive X-ray spectroscopy (TEM-EDX) and X-ray photoelectron spectroscopy (XPS). The Brunauer-Emmett-Teller (BET) and Langmuir surface areas of the prepared Au(5)-zeolite catalyst were found to be 644 and 929 m2g−1 respectively. Goldmodified zeolites performed as an efficient catalytic system for N-arylation of indazole using diverse aryl halides afforded N1 arylated products in appreciable yield under mild reaction conditions. The catalyst was reusable for at least five times with only a marginal loss of activity. This simple, effective and environmentally benign heterogeneous protocol provides a safer alternative to hazardous, corrosive and more polluting conventional catalysts.

  我们在此报告使用金修饰沸石（Au-zeolites）作为高效催化体系，对吲唑与芳基卤化物进行 N-芳基化反应。我们采用离子交换法制备了三种不同金负载的金沸石，并通过紫外可见漫反射光谱（UV-DRS）、透射电子显微镜和能量色散 X 射线光谱（TEM-EDX）以及 X 射线光电子能谱（XPS）对其进行了表征。制备的金（5）沸石催化剂的布鲁纳-艾美特-泰勒（BET）和朗缪尔表面积分别为 644 和 929 m2g-1。金改性沸石是一种高效的催化体系，可在温和的反应条件下，利用各种芳基卤化物对吲唑进行 N-芳基化反应，并以可观的产率获得 N1 芳基化产物。该催化剂可重复使用至少五次，活性仅略有下降。这种简单、有效和对环境无害的异构方案为危险、腐蚀性和污染性更强的传统催化剂提供了更安全的替代品。
• Regiodivergent Cu-Promoted, AcOH-Switchable Distal Versus Proximal Direct Cyanation of 1-Aryl-1<i>H</i>-indazoles and 2-Aryl-2<i>H</i>-indazoles via Aerobic Oxidative C–H Bond Activation
  作者：Richa Sharma、Sandeep Chaudhary

  DOI：10.1021/acs.joc.2c01603

  日期：2022.12.16

  A copper-promoted regiodivergent, AcOH-switchable, distal and proximal direct cyanation of N-aryl-(1H/2H)-indazoles via aerobic oxidative C(sp2)–H bond activation has been developed. The inclusion or exclusion of AcOH as an additive is the foremost cause for the positional switch in the C–CN bond formation method that results in (C-2′)-cyanated 2-aryl-2H-indazoles 3a–j, (C-2′)-cyanated 1-aryl-1H-indazoles

  开发了一种通过有氧氧化 C(sp 2 )–H 键激活对N -芳基-(1 H /2 H )-吲唑进行铜促进区域发散、AcOH 可切换、远端和近端直接氰化反应。添加或排除 AcOH 作为添加剂是导致 (C-2')-氰化 2-芳基-2 H-吲唑3a-j的 C-CN 键形成方法中位置转换的主要原因，(C -2')-cyanated 1-aryl-1 H -indazoles 4a–j [distal], 或 C-3 cyanated 2-aryl-2 H -indazoles 5a–i [proximal] 产品具有良好至优异的产率并显示出各种功能群体耐受性。氰化物（CN– ) 离子替代物是通过二甲基甲酰胺和碘化铵 (NH 4 I) 的统一生成的。使用分子氧（有氧氧化策略）作为一种清洁安全的氧化剂可以带来大量的附加值。通过将合成的氰化产物转化为许多其他官能团，证明了所开发协议的进一步针对性，这无疑
• Picciola; Ravenna; Carenini, Farmaco, Edizione Scientifica, 1981, vol. 36, # 12, p. 1037 - 1056
  作者：Picciola、Ravenna、Carenini、Gentili、Riva

  DOI：——

  日期：——