sodium (3,5-dibromoisonicotinoyl)(4-methoxybenzoyl)amide | 1446393-82-3

• 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: sodium (3,5-dibromoisonicotinoyl)(4-methoxybenzoyl)amide
• 英文别名: sodium (3,5-dibromoisonicotinoyl)(4-methoxybenzoy)amide；sodium;N-(3,5-dibromopyridine-4-carbonyl)-4-methoxybenzenecarboximidate
• CAS: 1446393-82-3
• 化学式: C₁₄H₉Br₂N₂O₃*Na
• 分子量: 436.035
• InChiKey: AEDUQOYDJRYSLM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.43
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sodium (3,5-dibromoisonicotinoyl)(4-methoxybenzoyl)amide 以 二甲基亚砜 为溶剂， 反应 0.33h， 以94%的产率得到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
• 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 、 mineral oil 、 叔丁醇 为溶剂， 反应 3.5h， 生成 sodium (3,5-dibromoisonicotinoyl)(4-methoxybenzoyl)amide
  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.
• 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.