2,4-diphenyl-6-(trifluoromethyl)quinazoline | 1446786-09-9

• 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-diphenyl-6-(trifluoromethyl)quinazoline
• CAS: 1446786-09-9
• 化学式: C₂₁H₁₃F₃N₂
• 分子量: 350.343
• InChiKey: CISONBYLPNJTPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  n-苄基苯甲酰胺 在 氯化亚砜 、 四溴化碳 、 rose bengal 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 12.5h， 生成 2,4-diphenyl-6-(trifluoromethyl)quinazoline
  参考文献：
  名称：

  Transition Metal-Free Visible Light-Driven Photoredox Oxidative Annulation of Arylamidines

  摘要：

  A fast catalytic synthesis of multisubstituted quinazolines from readily available amidines via visible light-mediated oxidative C(sp(3))-C(sp(2)) bond formation has been established. This reaction is a metal-free oxidative coupling catalyzed by a photoredox organocatalyst. The protocol features low catalyst loading (1 mol %).

  DOI：

  10.1021/acs.joc.5b02366

文献信息

• Palladium-Catalyzed Three-Component Tandem Process: One-Pot Assembly of Quinazolines
  作者：Kun Hu、Qianqian Zhen、Julin Gong、Tianxing Cheng、Linjun Qi、Yinlin Shao、Jiuxi Chen

  DOI：10.1021/acs.orglett.8b01070

  日期：2018.5.18

  The first example of the palladium-catalyzed, three-component tandem reaction of 2-aminobenzonitriles, aldehydes, and arylboronic acids has been developed, providing a new approach for one-pot assembly of diverse quinazolines in moderate to good yields. A noteworthy feature of this method is the tolerance of bromo and iodo groups, which affords versatility for further synthetic manipulations. Preliminary

  已经开发出了钯催化的2-氨基苄腈，醛和芳基硼酸的三组分串联反应的第一个例子，这为中度到良好收率的各种喹唑啉的一锅法组装提供了一种新方法。该方法的一个值得注意的特征是对溴和碘基的耐受性，为进一步的合成操作提供了多功能性。初步的机械实验表明，该串联过程涉及通过氰基的催化碳钯反应形成喹唑啉的两种可能的机械途径。
• 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。
• One-pot synthesis of quinazoline derivatives via [2+2+2] cascade annulation of diaryliodonium salts and two nitriles
  作者：Xiang Su、Chao Chen、Yong Wang、Junjie Chen、Zhenbang Lou、Ming Li

  DOI：10.1039/c3cc43216e

  日期：——

  An efficient one-pot approach to multiple substituted quinazolines with diaryliodonium salt 1, and two nitriles 2 has been presented. The reaction enables great flexibility of the substitution patterns on quinazolines and is applicable to two different nitriles to give a regio-selective product.

  本研究提出了一种用二月碘鎓盐 1 和两种腈类化合物 2 一锅制备多种取代喹唑啉的高效方法。该反应使喹唑啉的取代模式具有极大的灵活性，并适用于两种不同的腈，从而得到具有区域选择性的产物。
• Solvent/Oxidant-Switchable Synthesis of Multisubstituted Quinazolines and Benzimidazoles via Metal-Free Selective Oxidative Annulation of Arylamidines
  作者：Jian-Ping Lin、Feng-Hua Zhang、Ya-Qiu Long

  DOI：10.1021/ol500864r

  日期：2014.6.6

  A fast and simple divergent synthesis of multisubstituted quinazolines and benzimidazoles was developed from readily available amidines, via iodine(III)-promoted oxidative C(sp(3))-C(sp(2)) and C(sp(2))-N bond formation in nonpolar and polar solvents, respectively. Further selective synthesis of quinazolines in polar solvent was realized by TEMPO-catalyzed sp(3)C-H/sp(2)C-H direct coupling of the amidine with K2S2O8 as the oxidant. No metal, base, or other additives were needed.