3-benzyl-2-(pyridin-3-yl)quinazolin-4(3H)-one | 450378-15-1

• 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: 3-benzyl-2-(pyridin-3-yl)quinazolin-4(3H)-one
• 英文别名: 3-Benzyl-2-pyridin-3-ylquinazolin-4-one
• CAS: 450378-15-1
• 化学式: C₂₀H₁₅N₃O
• 分子量: 313.359
• InChiKey: WKNIUPJAWCBAIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苄胺 在 copper(l) iodide 、 lithium tert-butoxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 3-benzyl-2-(pyridin-3-yl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Ligand-Free Pd-Catalyzed and Copper-Assisted C–H Arylation of Quinazolin-4-ones with Aryl Iodides under Microwave Heating

  摘要：

  A microwave-assisted method for the palladium-catalyzed direct arylation of quinazolin-4-one has been developed under copper-assistance. This method is applicable to a wide range of aryl iodides and substituted (2H)-quinazolin-4-ones. This protocol provides a simple and efficient way to synthesize biologically relevant 2-arylquinazolin-4-one backbones.

  DOI：

  10.1021/acs.orglett.5b00467

文献信息

• Cu/Pd-Catalyzed C-2-H Arylation of ­Quinazolin-4(3<i>H</i>)-ones with (Hetero)aryl Halides
  作者：Julien Godeau、Marine Harari、Sylvain Laclef、Emmanuel Deau、Corinne Fruit、Thierry Besson

  DOI：10.1002/ejoc.201501129

  日期：2015.12

  The regiospecific C-2–H arylation of N-3-substituted quinazolin-4(3H)-ones with a wide range of aryl or (hetero)aryl halides under microwave irradiation was studied. A ligand-dependent palladium/copper bicatalytic system was developed and allowed direct cross-coupling with a variety of (hetero)aryl halides. This useful and scalable procedure promotes the construction of C(sp2)–C(sp2) bonds from arenes

  研究了在微波辐射下，N-3-取代的喹唑啉-4（3H）-酮与多种芳基或（杂）芳基卤化物的区域特异性C-2-H芳基化。开发了一种依赖于配体的钯/铜双催化系统，并允许与各种（杂）芳基卤化物直接交叉偶联。这种有用且可扩展的过程促进了从芳烃或（杂）芳烃和芳基或（杂）芳基溴化物和氯化物以一种省时的策略构建 C(sp2)–C(sp2) 键。还研究了使用碘苯将反应扩展到各种 N-3-取代的喹唑啉-4(3H)-酮以及该方法的范围和局限性。
• An efficient synthesis of 2,3-diaryl (3H)-quinazolin-4-ones via imidoyl chlorides
  作者：Andrew Kalusa、Nicola Chessum、Keith Jones

  DOI：10.1016/j.tetlet.2008.07.091

  日期：2008.10

  A practical and efficient three step synthetic route to 2,3-diaryl (3H)-quinazolin-4-ones has been developed. The key step involves microwave-assisted condensation of an imidoyl chloride with an aryl amine. This methodology affords the products cleanly and in high yields.

  已开发出实用且有效的三步合成路线，以合成2,3-二芳基（3 H）-喹唑啉-4-酮。关键步骤涉及亚氨酰氯与芳基胺的微波辅助缩合。这种方法可以清洁，高产地提供产品。
• Ligand-Free Pd-Catalyzed and Copper-Assisted C–H Arylation of Quinazolin-4-ones with Aryl Iodides under Microwave Heating
  作者：Sylvain Laclef、Marine Harari、Julien Godeau、Isabelle Schmitz-Afonso、Laurent Bischoff、Christophe Hoarau、Vincent Levacher、Corinne Fruit、Thierry Besson

  DOI：10.1021/acs.orglett.5b00467

  日期：2015.4.3

  A microwave-assisted method for the palladium-catalyzed direct arylation of quinazolin-4-one has been developed under copper-assistance. This method is applicable to a wide range of aryl iodides and substituted (2H)-quinazolin-4-ones. This protocol provides a simple and efficient way to synthesize biologically relevant 2-arylquinazolin-4-one backbones.