N-[4-Bromo-2-(3-oxo-3,4,5,6-tetrahydro-pyrazin-2-yl)-phenyl]-acetamide | 193959-49-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[4-Bromo-2-(3-oxo-3,4,5,6-tetrahydro-pyrazin-2-yl)-phenyl]-acetamide
• 英文别名: N-[4-bromo-2-(6-oxo-2,3-dihydro-1H-pyrazin-5-yl)phenyl]acetamide
• CAS: 193959-49-8
• 化学式: C₁₂H₁₂BrN₃O₂
• 分子量: 310.15
• InChiKey: PRDIAQQMYSJUGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-[4-Bromo-2-(3-oxo-3,4,5,6-tetrahydro-pyrazin-2-yl)-phenyl]-acetamide 在 氢氧化钾 、 水 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二苯醚 、 乙醇 、 二甲基亚砜 为溶剂， 反应 36.0h， 生成 2-(8-bromopyrazino[2,3-b]indol-5-yl)-N,N-dimethylethanamine
  参考文献：
  名称：

  Synthesis of 5H-Pyrazino[2,3-b]indoles from Indole-2,3-dione Derivatives.

  摘要：

  Reaction of N-acetylindol-2,3-diones with ethylenediamines gave the dihydro-pyrazinones 11, which could, after dehydrogenation and deacetylation be transformed to the corresponding 5H-pyrazino[2,3-b]indoles 5. N,N-Dimethylaminoethylation of the anion of 5 occurred selectively in the 5-position. Thermolysis of 1-pyrazinylbenzotriazole gave pyrazino[1,2-a]-benzimidazole 33 and no 5H-pyrazino[2,3-b] indole.

  DOI：

  10.3891/acta.chem.scand.51-0742
• 作为产物：
  描述：

  1-acetyl-5-bromoindoline-2,3-dione 以 乙醇 为溶剂， 反应 3.0h， 生成 N-[4-Bromo-2-(3-oxo-3,4,5,6-tetrahydro-pyrazin-2-yl)-phenyl]-acetamide
  参考文献：
  名称：

  Synthesis of 5H-Pyrazino[2,3-b]indoles from Indole-2,3-dione Derivatives.

  摘要：

  Reaction of N-acetylindol-2,3-diones with ethylenediamines gave the dihydro-pyrazinones 11, which could, after dehydrogenation and deacetylation be transformed to the corresponding 5H-pyrazino[2,3-b]indoles 5. N,N-Dimethylaminoethylation of the anion of 5 occurred selectively in the 5-position. Thermolysis of 1-pyrazinylbenzotriazole gave pyrazino[1,2-a]-benzimidazole 33 and no 5H-pyrazino[2,3-b] indole.

  DOI：

  10.3891/acta.chem.scand.51-0742

文献信息

• An efficient microwave-assisted synthesis of dihydropyrazinones and bis-benzoylketones
  作者：Mamun M. Hossain、Rabiul M. Islam、Sukanta K. Saha、Mohammad K. Islam

  DOI：10.1016/j.tetlet.2009.12.057

  日期：2010.2

  Microwave-assisted modified Sandmeyer reactions of oximinoacetanilides, themselves obtained from substituted primary aromatic amines, in concentrated H2SO4 give isatins. N-Acetylisatins undergo ring cleavage and subsequent ring closing with alkanediamines in the presence of ethanol under MW irradiation to give the corresponding dihydropyrazinones in excellent yields. Modification of the reaction conditions affords bis-benzoyl ketones under MW irradiation. (C) 2009 Elsevier Ltd. All rights reserved.