3-(2-thiophenyl)pyrido[2,3-b]pyrazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶吡嗪类
• 英文名称: 3-(2-thiophenyl)pyrido[2,3-b]pyrazine
• 英文别名: 3-(2-thienyl)pyrido[2,3-b]pyrazine；3-Thiophen-2-ylpyrido[2,3-b]pyrazine
• 化学式: C₁₁H₇N₃S
• 分子量: 213.263
• InChiKey: RGDBKTWMWPOLDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.67
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-噻吩基乙二醛 、 2,3-二氨基吡啶 在 氟化铵 作用下， 以 甲醇 、 水 为溶剂， 反应 0.25h， 以95%的产率得到3-(2-thiophenyl)pyrido[2,3-b]pyrazine
  参考文献：
  名称：

  A Combined Experimental and Theoretical Study of the Ammonium Bifluoride Catalyzed Regioselective Synthesis of Quinoxalines and Pyrido[2,3-b]pyrazines

  摘要：

  Ammonium bifluoride was efficiently used at a 0.5 mol% loading to catalyze the cyclocondensation of 1,2-arylenediamines with 1,2-dicarbonyl compounds at room temperature in methanol-water to give quinoxalines or pyrido[2,3-b]pyrazines in excellent yields. Importantly, 2,8-disubstituted quinoxalines and 3-substituted pyrido[2,3-b]pyrazines were regioselectively formed by the reaction of arylglyoxals with 3-methylbenzene-1,2-diamine or pyridine-2,3-diamine, respectively. An analysis of the density functional theory reactivity indices explained the catalytic role of ammonium bifluoride.

  DOI：

  10.1055/s-0034-1380678

文献信息

• Saccharin as an Organocatalyst for Quinoxalines and Pyrido[2,3-<i>b</i>]pyrazines Syntheses
  作者：Frédéric Lassagne、Floris Chevallier、Florence Mongin

  DOI：10.1080/00397911.2013.795596

  日期：2014.1.2

  A room-temperature procedure using saccharin as catalyst has been described for the cyclocondensation of different 1,2-arylenediamines with various 1,2-dicarbonyl compounds, yielding either quinoxalines or pyrido[2,3-b]pyrazines. The reactions proceed in very short reaction times in methanol, and the target heterocycles are isolated in quantitative yields after addition of water, filtration, and drying. Substituted pyrido[2,3-b]pyrazines can also be reached regioselectively by reacting -ketoaldehydes with 2,3-diaminopyridine. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
• A Combined Experimental and Theoretical Study of the Ammonium Bifluoride Catalyzed Regioselective Synthesis of Quinoxalines and Pyrido[2,3-b]pyrazines
  作者：Frédéric Lassagne、Florence Mongin、Luis Domingo、Floris Chevallier、Thierry Roisnel、Vincent Dorcet

  DOI：10.1055/s-0034-1380678

  日期：——

  Ammonium bifluoride was efficiently used at a 0.5 mol% loading to catalyze the cyclocondensation of 1,2-arylenediamines with 1,2-dicarbonyl compounds at room temperature in methanol-water to give quinoxalines or pyrido[2,3-b]pyrazines in excellent yields. Importantly, 2,8-disubstituted quinoxalines and 3-substituted pyrido[2,3-b]pyrazines were regioselectively formed by the reaction of arylglyoxals with 3-methylbenzene-1,2-diamine or pyridine-2,3-diamine, respectively. An analysis of the density functional theory reactivity indices explained the catalytic role of ammonium bifluoride.