sodium (3-bromoisonicotinoyl)(3-methylbenzoyl)amide | 1446393-76-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: sodium (3-bromoisonicotinoyl)(3-methylbenzoyl)amide
• CAS: 1446393-76-5
• 化学式: C₁₄H₁₀BrN₂O₂*Na
• 分子量: 341.139
• InChiKey: ZILQASFBDDDGKJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  65.38
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  sodium (3-bromoisonicotinoyl)(3-methylbenzoyl)amide 以 二甲基亚砜 为溶剂， 反应 0.5h， 以72%的产率得到2-(m-tolyl)-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-溴吡啶-4-酰胺 、 间甲基苯甲酰氯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.0h， 以98%的产率得到sodium (3-bromoisonicotinoyl)(3-methylbenzoyl)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