2-(4-nitrophenyl)-4-phenylquinazoline | 84570-81-0

• 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-nitrophenyl)-4-phenylquinazoline
• CAS: 84570-81-0
• 化学式: C₂₀H₁₃N₃O₂
• mdl: MFCD00223773
• 分子量: 327.342
• InChiKey: IUOUNQOIBQSNNB-UHFFFAOYSA-N

物化性质

• 熔点：
  196-199 °C(Solv: ligroine (8032-32-4))
• 沸点：
  439.8±37.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-nitrophenyl)-4-phenylquinazoline 在 镍 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以63%的产率得到2-(4-aminophenyl)-4-phenylquinazoline
  参考文献：
  名称：

  Kofanov; Sosnina; Danilova, Russian Journal of Applied Chemistry, 1999, vol. 72, # 5, p. 850 - 852

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基苯甲酰替苯胺 在 氯化亚砜 、 碘苯二乙酸 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 9.17h， 生成 2-(4-nitrophenyl)-4-phenylquinazoline
  参考文献：
  名称：

  Solvent/Oxidant-Switchable Synthesis of Multisubstituted Quinazolines and Benzimidazoles via Metal-Free Selective Oxidative Annulation of Arylamidines

  摘要：

  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.

  DOI：

  10.1021/ol500864r

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。
• I2-Catalyzed three-component protocol for the synthesis of quinazolines
  作者：Sumit Kumar Panja、Nidhi Dwivedi、Satyen Saha

  DOI：10.1016/j.tetlet.2012.08.016

  日期：2012.11

  moderate temperature (40 °C) without the involvement of any chromatographic purification. Oxidizing and Lewis acidic properties of molecular I2 have been utilized here. Detailed mechanism has been established based on an isolated intermediate and its single crystal X-ray crystallographic structure.

  提出了一种高效的一锅三组分策略，用于合成高度官能化的喹唑啉衍生物。在I 2-催化剂存在下，2-氨基二苯甲酮，芳族醛和乙酸铵的混合物即使在中等温度（40°C）下也能以优异的产率提供所需的产物，而无需进行任何色谱纯化。这里已经利用了分子I 2的氧化和路易斯酸性。基于分离的中间体及其单晶X射线晶体结构，建立了详细的机理。
• Copper-catalyzed aerobic oxidative decarboxylative amination of arylacetic acids: a facile access to 2-arylquinazolines
  作者：Yizhe Yan、Miaomiao Shi、Bin Niu、Xiangping Meng、Changrui Zhu、Gengyao Liu、Ting Chen、Yanqi Liu

  DOI：10.1039/c6ra04195g

  日期：——

  An efficient copper-catalyzed oxidative decarboxylative amination of arylacetic acids with 2-aminobenzoketones and ammonium acetate under oxygen atmosphere was first developed. This reaction represents a novel avenue for 2-arylquinazolines in good...

  首先开发了在氧气气氛下用2-氨基苯甲酮和乙酸铵对芳酸的铜进行催化的高效氧化脱羧胺化反应。该反应代表了2-芳基喹唑啉在良好条件下的新途径。
• Efficient One-Pot Synthesis of Quinazoline and Benzopyrano[2,3-<i>d</i>]pyrimidine Derivatives Catalyzed by<i>N</i>-Bromosulfonamides
  作者：Ramin Ghorbani-Vaghei、Mina Shirzadi-Ahodashti、Fattemeh Eslami、Seyedeh Mina Malaekehpoor、Zahra Salimi、Zahra Toghraei-Semiromi、Samira Noori

  DOI：10.1002/jhet.2570

  日期：2017.1

  N'‐tetrabromobenzene‐1,3‐disulfonamide and poly(N,N’‐dibromo‐N‐ethyl‐benzene‐1,3‐disulfonamide) were used as efficient catalysts for one‐pot synthesis of new quinazoline derivatives from various aldehydes, 2‐amino‐benzophenone, and ammonium acetate in good to excellent yields and new benzopyrano[2,3‐d]pyrimidine derivatives from salicylic aldehydes, various cyclic amines, and malononitrile in good to high yields.

  N，N，N'，N'-四溴苯-1,3-二磺酰胺和聚（N，N'-二溴N-乙基-苯-1,3-二磺酰胺）被用作高效催化剂，用于一锅合成来自各种醛的新喹唑啉衍生物，2-氨基二苯甲酮和乙酸铵，收率高至优异；来自水杨醛，各种环胺和丙二腈的新型苯并吡喃并[2,3- d ]嘧啶衍生物，收率高至高。
• Ecofriendly and Efficient One-Pot Procedure for the Synthesis of Quinazoline Derivatives Catalyzed by an Acidic Ionic Liquid Under Aerobic Oxidation Conditions
  作者：Minoo Dabiri、Peyman Salehi、Mahboobeh Bahramnejad

  DOI：10.1080/00397910903395250

  日期：2010.9.30

  three-component condensation reaction between 2-aminobenzophenone derivatives, formaldehyde or aromatic aldehydes, and ammonium acetate efficiently provides substituted quinazolines in a one-pot reaction in the presence of Brönsted acidic ionic liquid, 1-methylimidazolium triflouroacetate ([Hmim]TFA), in conjunction with aerobic oxidation. The ionic liquid was separated from the reaction mixture by simple

  在 Brönsted 酸性离子液体、1-甲基咪唑鎓三氟乙酸盐 ([Hmim]TFA) 存在下，2-氨基二苯甲酮衍生物、甲醛或芳香醛和乙酸铵之间的三组分缩合反应在一锅反应中有效地提供取代的喹唑啉，与有氧氧化相结合。通过简单的萃取将离子液体从反应混合物中分离出来，并且在活性没有显着损失的情况下再循环3次。