2-amino-6-(2-oxo-2-phenylethylsulfanyl)-4-phenylpyridine-3,5-dicarbonitrile | 189278-39-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-6-(2-oxo-2-phenylethylsulfanyl)-4-phenylpyridine-3,5-dicarbonitrile
• 英文别名: 2-amino-6-[(2-oxo-2-phenylethyl)thio]-4-phenylpyridine-3,5-dicarbonitrile；2-Amino-6-phenacylsulfanyl-4-phenylpyridine-3,5-dicarbonitrile
• CAS: 189278-39-5
• 化学式: C₂₁H₁₄N₄OS
• 分子量: 370.434
• InChiKey: YWRGUTZMDNPVNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-6-(2-oxo-2-phenylethylsulfanyl)-4-phenylpyridine-3,5-dicarbonitrile 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 3,6-diamino-2-benzoyl-4-phenylthieno[2,3-b]pyridine-5-carbonitrile
  参考文献：
  名称：

  Synthesis of Novel Fused Heterocycles Based on 6-Amino-4-phenyl-2-thioxo-1,2-dihydropyridine-3,5-dicarbonitrile

  摘要：

  Under phase transfer catalysis conditions, 6‐amino‐4‐phenyl‐2‐thioxo‐1,2‐dihydropyridine‐3,5‐dicarbonitrile (1) was allowed to react with halo compounds, acrylonitrile, chloroacetyl chloride, ethyl cyanoacetate, formamide, triethylorthoformate, or formic acid to give new derivatives of fused pyridines 2–22, respectively. Acetylation of compound 1 using acetic anhydride afforded product 23, which in turn underwent intramolecular cyclization in pyridine to give the corresponding pyrido[2,3‐d]pyrimidine 24.

  DOI：

  10.1002/jhet.2522
• 作为产物：
  描述：

  2-amino-4-phenyl-6-phenylsulfanyl-pyridine-3,5-dicarbonitrile 在 sodium sulfide 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 2-amino-6-(2-oxo-2-phenylethylsulfanyl)-4-phenylpyridine-3,5-dicarbonitrile
  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

• US7504421B2
  申请人：——

  公开号：US7504421B2

  公开（公告）日：2009-03-17
• Synthesis of Novel Fused Heterocycles Based on 6-Amino-4-phenyl-2-thioxo-1,2-dihydropyridine-3,5-dicarbonitrile
  作者：H. Abdel-Ghany、A. M. El-Sayed、A. A. Amer、A. M. Ahmed

  DOI：10.1002/jhet.2522

  日期：2016.11

  Under phase transfer catalysis conditions, 6‐amino‐4‐phenyl‐2‐thioxo‐1,2‐dihydropyridine‐3,5‐dicarbonitrile (1) was allowed to react with halo compounds, acrylonitrile, chloroacetyl chloride, ethyl cyanoacetate, formamide, triethylorthoformate, or formic acid to give new derivatives of fused pyridines 2–22, respectively. Acetylation of compound 1 using acetic anhydride afforded product 23, which in turn underwent intramolecular cyclization in pyridine to give the corresponding pyrido[2,3‐d]pyrimidine 24.
• 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.