5-bromo-2-(1-methyl-1H-pyrrol-2-yl)-4H-pyrido[4,3-e][1,3]oxazin-4-one | 1446357-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡啶类
• 英文名称: 5-bromo-2-(1-methyl-1H-pyrrol-2-yl)-4H-pyrido[4,3-e][1,3]oxazin-4-one
• CAS: 1446357-48-7
• 化学式: C₁₂H₈BrN₃O₂
• 分子量: 306.118
• InChiKey: NYLICITUFOBDOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  60.92
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(1-methyl-1H-pyrrol-2-yl)-4H-pyrido[4,3-e][1,3]oxazin-4-one 、 苯甲脒 以 乙醇 为溶剂， 反应 0.17h， 以67%的产率得到5-bromo-4-(4-(1-methyl-1H-pyrrol-2-yl)-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：

  sodium (3,5-dibromoisonicotinoyl)(1-methyl-1H-pyrrole-2-carbonyl)amide 以 二甲基亚砜 为溶剂， 反应 0.33h， 以80%的产率得到5-bromo-2-(1-methyl-1H-pyrrol-2-yl)-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