3,6-diamino-2-benzoyl-4-(4-methylphenyl)thieno[2,3-b]pyridine-5-carbonitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-diamino-2-benzoyl-4-(4-methylphenyl)thieno[2,3-b]pyridine-5-carbonitrile
• 化学式: C₂₂H₁₆N₄OS
• 分子量: 384.461
• InChiKey: ABTRTOFSGGSAGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-amino-6-phenylsulfanyl-4-p-tolyl-pyridine-3,5-dicarbonitrile 在 sodium sulfide 、 sodium ethanolate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 3,6-diamino-2-benzoyl-4-(4-methylphenyl)thieno[2,3-b]pyridine-5-carbonitrile
  参考文献：
  名称：

  Cascade Synthesis of Thieno[2,3-b]pyridines by Using Intramolecular Cyclization Reactions of 3-Cyano-2-(organylmethylthio)pyridines

  摘要：

  2-Amino-4-aryl-6-mercaptopyridine-3,5-dicarbonitriles as starting materials have been prepared by reducing of 2-amino-4-aryl-6-(phenylthio)pyridine-3,5-dicarbonitrile derivatives which were synthesized on stepwise one-pot three component reaction of malononitrile, aldehydes and thiophenol in the presence of base catalysts such as triethylamine, high surface area (HSA) MgO or nanocrystalline magnesium oxide. Alkylation of 2-amino-4-aryl-6- mercaptopyridine-3,5-dicarbonitriles with alpha-halogen compounds in presence of sodium alkoxide as base catalyst followed with cyclization afforded thethieno[2,3-b]pyridine derivatives in excellent yields and in a short reaction time.

  DOI：

  10.5935/0103-5053.20150309

文献信息

• Cascade Synthesis of Thieno[2,3-<i>b</i>]pyridines by Using Intramolecular Cyclization Reactions of 3-Cyano-2-(organylmethylthio)pyridines
  作者：Fatemeh Alinaghizadeh、Mahboobeh Zahedifar、Mohammad Seifi、Hassan Sheibani

  DOI：10.5935/0103-5053.20150309

  日期：——

  2-Amino-4-aryl-6-mercaptopyridine-3,5-dicarbonitriles as starting materials have been prepared by reducing of 2-amino-4-aryl-6-(phenylthio)pyridine-3,5-dicarbonitrile derivatives which were synthesized on stepwise one-pot three component reaction of malononitrile, aldehydes and thiophenol in the presence of base catalysts such as triethylamine, high surface area (HSA) MgO or nanocrystalline magnesium oxide. Alkylation of 2-amino-4-aryl-6- mercaptopyridine-3,5-dicarbonitriles with alpha-halogen compounds in presence of sodium alkoxide as base catalyst followed with cyclization afforded thethieno[2,3-b]pyridine derivatives in excellent yields and in a short reaction time.