5-bromo-2-(4-methoxyphenyl)-4H-pyrido[4,3-e][1,3]oxazin-4-one | 1446357-47-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-bromo-2-(4-methoxyphenyl)-4H-pyrido[4,3-e][1,3]oxazin-4-one
• 英文别名: 5-Bromo-2-(4-methoxyphenyl)pyrido[4,3-e][1,3]oxazin-4-one；5-bromo-2-(4-methoxyphenyl)pyrido[4,3-e][1,3]oxazin-4-one
• CAS: 1446357-47-6
• 化学式: C₁₄H₉BrN₂O₃
• 分子量: 333.141
• InChiKey: RFRQAZQDIAHHMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 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：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(4-methoxyphenyl)-4H-pyrido[4,3-e][1,3]oxazin-4-one 、 苯甲脒 以 乙醇 为溶剂， 反应 0.17h， 以81%的产率得到5-bromo-4-(4-(4-methoxyphenyl)-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：

  3,5-二溴-4-氰吡啶 在 sodium hydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二甲基亚砜 、 mineral oil 、 叔丁醇 为溶剂， 反应 3.83h， 生成 5-bromo-2-(4-methoxyphenyl)-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

• 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
• Preparation of Halogen-Containing 4<i>H</i>-Pyrido[<i>e</i>][1,3]oxazin-4-ones and Their Transformation into 2-Hydroxypyridinyl-Substituted 1,2,4-Oxadiazoles and 1,2,4-Triazoles
  作者：Laetitia Le Falher、Omar Ben Ayad、Ozge Ziyaret、Candice Botuha、Serge Thorimbert、Franck Slowinski

  DOI：10.1002/ejoc.201500277

  日期：2015.6

  functionalisation. We also present the discovery of a new, rapid, and complementary access to 2-substituted 4H-benzo[e][1,3]oxazinones. Finally, the one-step transformation of some of these pyrido-oxazinones into the corresponding hydroxypyridyl-substituted 1,2,4-oxadiazoles and 1,2,4-triazoles was explored, and the regioselectivity of the reaction was proved by X-ray crystallography.

  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。
• 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.
• Expeditive Access to 2-Substituted 4<i>H</i>-Pyrido[1,3]oxazin-4-ones <i>via</i> an Intramolecular O-Arylation
  作者：Franck Slowinski、Omar Ben Ayad、Ozge Ziyaret、Candice Botuha、Laetitia Le Falher、Kamel Aouane、Serge Thorimbert

  DOI：10.1021/ol401516e

  日期：2013.7.19

  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.