5-bromo-2-(4-chlorophenyl)-4H-pyrido[4,3-e][1,3]oxazin-4-one | 1616763-11-1

• 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: 5-bromo-2-(4-chlorophenyl)-4H-pyrido[4,3-e][1,3]oxazin-4-one
• CAS: 1616763-11-1
• 化学式: C₁₃H₆BrClN₂O₂
• 分子量: 337.56
• InChiKey: QYTGKELVXBEVGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.99
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(4-chlorophenyl)-4H-pyrido[4,3-e][1,3]oxazin-4-one 、 苯甲脒 以 乙醇 为溶剂， 反应 0.17h， 以69%的产率得到5-bromo-4-(4-(4-chlorophenyl)-6-phenyl-1,3,5-triazin-2-yl)pyridin-3-ol
  参考文献：
  名称：

  Access to Pyridyl-Substituted 1,3,5-Triazines from 4H-Pyrido[1,3]oxazin-4-ones via a Cyclocondensation Process

  摘要：

  Pyridyl-substituted 1,3,5-triazines were synthesized in good to excellent yields via an unprecedented one-step cyclocondensation of 4H-pyrido[1,3]oxazin-4-ones with amidines at room temperature or under microwave irradiations. The broad applicability was demonstrated by 33 examples with a variety of amidines and three different 4H-pyrido[1,3]oxazin-4-one chemical series. In addition, a one-pot process from 4H-pyrido[1,3]oxazin-4-one precursors (imide sodium salts) was developed and led to the desired triazines compounds, thus allowing a one-step economy in their global synthetic preparation. This approach provides rapid access to pyridyl (or pyridone)-substituted 1,3,5-triazines with high potential in various fields of application.

  DOI：

  10.1021/jo5010668
• 作为产物：
  描述：

  3,5-dibromoisonicotinamide 在 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 1.33h， 生成 5-bromo-2-(4-chlorophenyl)-4H-pyrido[4,3-e][1,3]oxazin-4-one
  参考文献：
  名称：

  Access to Pyridyl-Substituted 1,3,5-Triazines from 4H-Pyrido[1,3]oxazin-4-ones via a Cyclocondensation Process

  摘要：

  Pyridyl-substituted 1,3,5-triazines were synthesized in good to excellent yields via an unprecedented one-step cyclocondensation of 4H-pyrido[1,3]oxazin-4-ones with amidines at room temperature or under microwave irradiations. The broad applicability was demonstrated by 33 examples with a variety of amidines and three different 4H-pyrido[1,3]oxazin-4-one chemical series. In addition, a one-pot process from 4H-pyrido[1,3]oxazin-4-one precursors (imide sodium salts) was developed and led to the desired triazines compounds, thus allowing a one-step economy in their global synthetic preparation. This approach provides rapid access to pyridyl (or pyridone)-substituted 1,3,5-triazines with high potential in various fields of application.

  DOI：

  10.1021/jo5010668

文献信息

• Chemoselective Access to π-Conjugated Heterocycles by Stille and Sonogashira Reactions on 2-Substituted 4<i>H</i>-Pyrido[<i>e</i>][1,3]oxazin-4-ones
  作者：Laetitia Le Falher、Amara Mumtaz、Anthony Nina Diogo、Serge Thorimbert、Candice Botuha

  DOI：10.1002/ejoc.201601338

  日期：2017.1.26

  Site-selective PdII-catalyzed cross-coupling reactions of 2-substituted-4H-pyrido[e][1,3]oxazin-4-ones were developed. C4and C5-alkynylated pyridooxazinones were thus obtained through Sonogashira coupling, whereas the efficient incorporation of (hetero)aryl and ethenyl substituents at the C5 position was achieved by Stille coupling. Finally, an example of

  开发了位点选择性 PdII 催化的 2-取代-4H-吡啶并[e][1,3]oxazin-4-ones 的交叉偶联反应。因此，通过 Sonogashira 偶联获得了 C4 和 C5-炔基化的吡啶并恶嗪酮，而通过 Stille 偶联实现了（杂）芳基和乙烯基取代基在 C5 位置的有效结合。最后，举个例子