2,4-di-p-tolylquinazoline | 1446786-00-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2,4-di-p-tolylquinazoline
• 英文别名: 2,4-Bis(4-methylphenyl)quinazoline；2,4-bis(4-methylphenyl)quinazoline
• CAS: 1446786-00-0
• 化学式: C₂₂H₁₈N₂
• 分子量: 310.398
• InChiKey: FMSPIJGIJKNGHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-di-p-tolylquinazoline 在 N-碘代丁二酰亚胺 、 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  One-pot regioselective C–H activation iodination–cyanation of 2,4-diarylquinazolines using malononitrile as a cyano source

  摘要：

  已开发出一种使用NIS和马来酸二腈进行2,4-芳基喹唑啉的一锅法腈化反应。

  DOI：

  10.1039/c9ra02979f
• 作为产物：
  描述：

  4(1H)-喹唑啉酮,2-(4-甲基苯基)- 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 2,4-di-p-tolylquinazoline
  参考文献：
  名称：

  Synthesis of 4-Arylquinazolines by Arylation of Quinazolin-4-ones under Mild Conditions

  摘要：

  An efficient route to 4-arylquinazolines via arylation of quinazolin-4-ones under mild condition is described. The reaction is carried out by the palladium-catalyzed coupling of quinazolin-4-ones with arylboronic acids in the presence of TsCl leading to 4-arylquinazolines in good to excellent yields.

  DOI：

  10.1055/s-0033-1339848

文献信息

• Four-component quinazoline synthesis from simple anilines, aromatic aldehydes and ammonium iodide under metal-free conditions
  作者：Jinjin Chen、Dan Chang、Fuhong Xiao、Guo-Jun Deng

  DOI：10.1039/c8gc02654h

  日期：——

  A four-component procedure for the preparation of substituted quinazolines from anilines, aromatic aldehydes and ammonium iodide is described. The C–H bond ortho to the amino group in anilines was directly functionalized under metal-free conditions. Two aldehydes were involved in this reaction and ammonium iodide was used as one of the nitrogen sources. This reaction provides a strategy for the facile

  描述了一种由苯胺，芳族醛和碘化铵制备取代的喹唑啉的四组分方法。的C-H键的邻位中的苯胺的氨基不含金属的条件下直接官能化。该反应涉及两种醛，碘化铵用作氮源之一。该反应提供了从简单的苯胺和其他容易获得的反应物容易地构建取代的喹唑啉的策略。
• Preparation of Quinazolines via a 2+2+2 Annulation from Aryldiazonium Salts and Nitriles
  作者：Mani Ramanathan、Shiuh-Tzung Liu

  DOI：10.1021/acs.joc.7b01325

  日期：2017.8.4

  A (2+2+2) modular synthesis of multisubstituted quinazolines has been realized by the direct reaction of aryldiazonium salts with two equivalent of nitriles. Reaction of aryldiazonium salt with a nitrile provides the initial formation of a reactive nitrilium ion, which is attacked by another molecule of nitrile followed by electrophilic cyclization to deliver the desired product. Notable flexibility

  通过芳基重氮盐与两个当量腈的直接反应，实现了多取代喹唑啉的（2 + 2 + 2）模块化合成。芳基重氮盐与腈的反应提供了反应性腈离子的初始形成，该离子被另一种腈分子攻击，随后进行亲电环化以提供所需的产物。该方法的优点是取代模式具有显着的灵活性，易于获得的底物，反应时间短，无过渡金属和克级合成。
• Ru(II)-Catalyzed C–H Activation and Annulation Reaction via Carbon–Carbon Triple Bond Cleavage
  作者：Rashmi Prakash、Bidisha R. Bora、Romesh C. Boruah、Sanjib Gogoi

  DOI：10.1021/acs.orglett.8b00643

  日期：2018.4.20

  An unprecedented Ru(II)-catalyzed C–H activation and annulation reaction, which proceeds via C–C triple bond cleavage, is reported. This reaction of 2-phenyldihydrophthalazinediones with alkynes, which works most efficiently in the presence of bidented ligand 1,3-bis(diphenylphosphino)propane, affords good yields of substituted quinazolines.

  据报道，空前的Ru（II）催化的CH活化和环化反应是通过CC的三键裂解而进行的。2-苯基二氢酞嗪二酮与炔烃的这种反应在双键配体1,3-双（二苯基膦基）丙烷的存在下最有效地进行，产生了高产率的取代喹唑啉。
• Rh(III)-catalyzed oxidative <i>ortho</i>-C–H alkylation of 2,4-diarylquinazoline with potassium alkyltrifluoroborates
  作者：Wei Gao、Chun Gong、Qin Yang、Jianjun Yuan、Linchu Xu、Yiyuan Peng

  DOI：10.1139/cjc-2017-0258

  日期：2017.10

  Alkyltrifluoroborates were used for Rh(III)-catalyzed ortho-alkylation of 2,4-disubstituted quinazoline via C–H bond activation. The reaction proceeded well with a broad substrate scope, providing a direct way to access high functional quinazoline core structure derivatives in yields up to 95%.

  烷基三氟硼酸盐用于通过 C-H 键活化对 2,4-二取代喹唑啉进行 Rh(III) 催化的邻位烷基化。该反应在广泛的底物范围内进行得很好，提供了一种以高达 95% 的产率获得高功能喹唑啉核心结构衍生物的直接方法。
• Palladium-Catalyzed and Quinazoline-Directed C–H Selective Acetoxylation of 2-Arylquinazolines
  作者：Yiyuan Peng、Song Wei、Banlai Ouyang、Zhihong Deng、Qin Yang

  DOI：10.1055/s-0037-1611908

  日期：2019.10

  successfully synthesized via the Pd-catalyzed and quinazoline-directed C–H activation/acetoxylation of the corresponding 2-arylquinazolines with iodobenzene diacetate in AcOH/Ac2O. A series of acetoxylated 2-arylquinazolines have been successfully synthesized via the Pd-catalyzed and quinazoline-directed C–H activation/acetoxylation of the corresponding 2-arylquinazolines with iodobenzene diacetate in AcOH/Ac2O

  抽象的 通过在相应的2-芳基喹唑啉在AcOH / Ac 2 O中用碘代苯二乙酸酯进行Pd催化和喹唑啉定向的CH活化/乙酰氧基化，已成功合成了一系列乙酰氧基化的2-芳基喹唑啉。 通过在相应的2-芳基喹唑啉在AcOH / Ac 2 O中用碘代苯二乙酸酯进行Pd催化和喹唑啉定向的CH活化/乙酰氧基化，已成功合成了一系列乙酰氧基化的2-芳基喹唑啉。