2-(p-tolylamino)quinazolin-4(3H)-one | 1791-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(p-tolylamino)quinazolin-4(3H)-one
• 英文别名: 4(1h)-Quinazolinone,2-[(4-methylphenyl)amino]-；2-(4-methylanilino)-3H-quinazolin-4-one
• CAS: 1791-51-1
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: MFFLANMMDQEHDT-UHFFFAOYSA-N

物化性质

• 熔点：
  268-270 °C
• 沸点：
  425.3±38.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  53.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(p-tolylamino)quinazolin-4(3H)-one 、 溴乙酸 以88%的产率得到
  参考文献：
  名称：

  VLAZENKO A. F.; MAZUR I. A.; KOCHERGIN P. M., FARMATSEVTICHNIJ ZH., 1977, HO 1, 88-90

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲苯异氰酸酯 在 palladium diacetate 、 caesium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(p-tolylamino)quinazolin-4(3H)-one
  参考文献：
  名称：

  Ligand-free palladium assisted insertion of isocyanides to urea derivatives for cascade synthesis of phenylamino-substituted quinazolinones

  摘要：

  Palladium catalyzed cascade coupling of substituted urea derivatives and tert-butyl isocyanide for the efficient synthesis of phenylamino-substituted quinazolinones has been developed in moderate to good yields. This method provides a short and alternative approach for the synthesis of quinazolinones derivatives which are valuable compounds with biological and pharmacological potentials. A plausible mechanistic scheme is proposed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.027

文献信息

• Synthesis of Aroylguanidines by an Unexpected Demethylation-Addition Cascade
  作者：Zhen Guo、Qing Qi、Ling Gu、Ling He

  DOI：10.1055/s-0033-1338511

  日期：——

  2-aminoquinazolinones derivatives from inexpensive reactants. A simple and efficient method was developed for the synthesis of N-aroyl-N′-arylguanidines under mild conditions by an unexpected demethylation–addition cascade reaction of readily available N-cyanoimidates with aryl amines. Moreover, 1-aryl-2-aminoquinazolin-4(1H)-ones and 2-(arylamino)quinazolin-4(3H)-ones can also be prepared by selective cyclization

  摘要 一种简单且有效的方法是用于合成的开发Ñ -aroyl- Ñ由容易获得的意想不到的去甲基化加成级联反应“温和的条件下-arylguanidines Ñ与芳基胺-cyanoimidates。此外，还可以通过（2-氟苯甲酰基）-或（2的选择性环化反应来制备1-芳基-2-氨基喹唑啉-4（1 H）-one和2-（芳基氨基）喹唑啉-4（3 H）-one。 -硝基苯甲酰基）胍。该方法为从廉价的反应物制备2-氨基喹唑啉酮衍生物提供了两种有吸引力的策略。 一种简单且有效的方法是用于合成的开发Ñ -aroyl- Ñ由容易获得的意想不到的去甲基化加成级联反应“温和的条件下-arylguanidines Ñ与芳基胺-cyanoimidates。此外，还可以通过（2-氟苯甲酰基）-或（2的选择性环化反应来制备1-芳基-2-氨基喹唑啉-4（1 H）-one和2-（芳基氨基）喹唑啉-4（3 H）-one。 -硝基
• Regioselective synthesis and biological evaluation of<i>N</i>-substituted 2-aminoquinazolin-4-ones
  作者：Zhen-Yuan Liao、Wen-Hsiung Yeh、Pen-Yuan Liao、Yu-Ting Liu、Ying-Cheng Chen、Yi-Hung Chen、Tsung-Han Hsieh、Chia-Chi Lin、Ming-Hsuan Lu、Yi-Song Chen、Ming-Chih Hsu、Tsai-Kun Li、Tun-Cheng Chien

  DOI：10.1039/c8ob00624e

  日期：——

  the Dimroth rearrangement in aqueous ethanolic sodium hydroxide gave exclusively the regioisomers, 2-(N-arylamino)quinazolin-4-ones. The regioselective synthesis of N-aryl-substituted 2-aminoquinazolin-4-ones can be further applied to the synthesis of benzimidazo[2,1-b]quinazolin-12-ones.

  在对-TsOH存在下，在t- BuOH中，在回流下，邻氨基苯甲酸甲酯与N-芳基氰酰胺的反应主要得到3-芳基喹唑啉-4-酮。相比之下，相同的反应物与TMSCl在60°C的t- BuOH中反应，然后在乙醇氢氧化钠水溶液中进行Dimroth重排，仅得到区域异构体2-（N-芳基氨基）喹唑啉-4-酮。N-芳基取代的2-氨基喹唑啉-4-酮的区域选择性合成可以进一步应用于苯并咪唑并[2，1- b ]喹唑啉-12-酮的合成。
• Continuous Recycling of Homogeneous Pd/Cu Catalysts for Cross-Coupling Reactions
  作者：Siddharth Sharma、K. C. Basavaraju、Ajay K. Singh、Dong-Pyo Kim

  DOI：10.1021/ol501802w

  日期：2014.8.1

  Given the importance of homogeneous catalysts recycling in organic chemistry, we have developed a unique microfluidic loop system for automated continuous recirculation of a soluble polymer supported metal catalyst for novel isocyanide cross-coupling reactions under thermomorphic multicomponent solvent (TMS) conditions. Our system provides an innovative approach for the chemical library synthesis of quinazolinone derivatives as well as an important intermediate of Merck's LTD4 antagonist "Singulair" with efficient continuous homogeneous catalyst recycling.
• VLASENKO A. F.; MANDRICHENKO B. E.; ROGULCHENKO G. K.; SINYAK R. S.; MAZU+, XIMIYA GETEROTSIKL. SOEDIN. <KGSS-AQ>, 1976, HO 6, 834-836
  作者：VLASENKO A. F.、 MANDRICHENKO B. E.、 ROGULCHENKO G. K.、 SINYAK R. S.、 MAZU+

  DOI：——

  日期：——
• Ligand-free palladium assisted insertion of isocyanides to urea derivatives for cascade synthesis of phenylamino-substituted quinazolinones
  作者：Siddharth Sharma、Abhilasha Jain

  DOI：10.1016/j.tetlet.2014.09.027

  日期：2014.10

  Palladium catalyzed cascade coupling of substituted urea derivatives and tert-butyl isocyanide for the efficient synthesis of phenylamino-substituted quinazolinones has been developed in moderate to good yields. This method provides a short and alternative approach for the synthesis of quinazolinones derivatives which are valuable compounds with biological and pharmacological potentials. A plausible mechanistic scheme is proposed. (C) 2014 Elsevier Ltd. All rights reserved.