5-bromo-2-phenyl-4H-pyrido[4,3-e][1,3]oxazin-4-one | 1446357-45-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-bromo-2-phenyl-4H-pyrido[4,3-e][1,3]oxazin-4-one
• 英文别名: 5-Bromo-2-phenylpyrido[4,3-e][1,3]oxazin-4-one
• CAS: 1446357-45-4
• 化学式: C₁₃H₇BrN₂O₂
• 分子量: 303.115
• InChiKey: KBYFVLIJOPPDLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-2-phenyl-4H-pyrido[4,3-e][1,3]oxazin-4-one 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以87%的产率得到5-bromo-4-(3-phenyl-1,2,4-oxadiazol-5-yl)pyridin-3-ol
  参考文献：
  名称：

  含卤素 4H-Pyrido[e][1,3]oxazin-4-ones 的制备及其转化为 2-Hydroxypyridinyl-Substituted 1,2,4-Oxadiazoles 和 1,2,4-Triazoles

  摘要：

  完整研究了原始含卤素的 4H-吡啶并 [e][1,3]oxazin-4-ones 的制备及其转化为 1,2,4-oxadiazoles 和 1,2,4-triazoles。从吡啶基亚胺钠盐开始，研究了三个系列化合物的分子内 O-芳基化的效率，在 C-2 位置具有不同的氟代、氯代和溴代苯基。最终的卤化化合物作为未来功能化的新合成子是令人感兴趣的。我们还介绍了对 2-取代 4H-苯并[e][1,3] 恶嗪酮的新的、快速的和互补的途径的发现。最后，探索了其中一些吡啶并恶嗪酮一步转化为相应的羟基吡啶基取代的 1,2,4-恶二唑和 1,2,4-三唑，并通过 X 射线证明了反应的区域选择性晶体学。

  DOI：

  10.1002/ejoc.201500277
• 作为产物：
  描述：

  sodium benzoyl(3,5-dibromoisonicotinoyl)amide 以 二甲基亚砜 为溶剂， 反应 0.33h， 以81%的产率得到5-bromo-2-phenyl-4H-pyrido[4,3-e][1,3]oxazin-4-one
  参考文献：
  名称：

  Expeditive Access to 2-Substituted 4H-Pyrido[1,3]oxazin-4-ones via an Intramolecular O-Arylation

  摘要：

  Unreported 2-substituted 4H-pyrido[e][1,3]oxazin-4-ones are synthesized via an unprecedented intramolecular O-arylation of N-aroyl- and N-heteroaroyl-(iso)nicotinamides under microwave irradiations, in good to excellent yields. The broad applicability was demonstrated by 24 examples with a variety of substituents at the 2-position of the final compounds and 3 possible positions for the nitrogen atom of the pyridine ring. In addition, transformation of one of these compounds into 2-hydroxypyridyl-substituted 1,2,4-triazole and 1,2,4-oxazinone was realized. This approach opens a rapid access to a new bicyclic heteroaromatic chemical series with high potential in medicinal chemistry.

  DOI：

  10.1021/ol401516e

文献信息

• Access to Pyridyl-Substituted 1,3,5-Triazines from 4<i>H</i>-Pyrido[1,3]oxazin-4-ones via a Cyclocondensation Process
  作者：Laetitia Le Falher、Omar Ben Ayad、Ozge Ziyaret、Alexander Mamontov、Candice Botuha、Serge Thorimbert、Franck Slowinski

  DOI：10.1021/jo5010668

  日期：2014.7.18

  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.