2-amino-4-(4-methylphenyl)-6-(2-aminophenylsulfanyl)pyridine-3,5-dicarbonitrile | 79359-37-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-4-(4-methylphenyl)-6-(2-aminophenylsulfanyl)pyridine-3,5-dicarbonitrile
• 英文别名: 2-Amino-6-(2-aminophenyl)sulfanyl-4-(4-methylphenyl)pyridine-3,5-dicarbonitrile
• CAS: 79359-37-8
• 化学式: C₂₀H₁₅N₅S
• 分子量: 357.439
• InChiKey: WKNGKISTSCJIGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(4-甲基亚苄基)-丙二腈 、 2-氨基苯硫醇 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以18%的产率得到2-amino-4-(4-methylphenyl)-6-(2-aminophenylsulfanyl)pyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  Synthetic Studies Using α,β-Unsaturated Nitriles: Facile Synthesis of Pyridine Derivatives

  摘要：

  DOI：

  10.1055/s-1981-29513

文献信息

• DBU-catalyzed three-component one-pot synthesis of highly functionalized pyridines in aqueous ethanol
  作者：Ritu Mamgain、Ram Singh、Diwan S. Rawat

  DOI：10.1002/jhet.32

  日期：2009.1

  1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) efficiently catalyzes three-component one-pot condensations of aldehyde, malononitrile, and thiophenol to produce highly functionalized pyridines in excellent yield in aqueous ethanol. J. Heterocyclic Chem., 46, 69 (2009).

  1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）有效催化醛的三组分一锅缩合，丙二腈和苯硫酚在乙醇水溶液中以优异的收率生产高度官能化的吡啶。杂环化学杂志，46，69（2009）。
• Synthesis of 2-amino-4-phenyl-6-(phenylsulfanyl)-3,5-dicyanopyridines by tandem reaction
  作者：Dong Hao、Zhong Yun-lei、Shen Xiao-peng、Yang Jin-ming、Fang Dong

  DOI：10.1007/s11164-012-0984-0

  日期：2014.2

  A novel basic ionic liquid, 1-(2-aminoethyl)pyridinium hydroxide, containing both Brønsted base and Lewis base sites has been used as an efficient catalyst for the synthesis of 2-amino-4-phenyl-6-(phenylsulfanyl)-3,5-dicyanopyridines. The condensation and oxidation tandem reaction of aldehydes, malononitrile, and thiols, performed in aqueous ethanol, afforded reasonable to good yields within 30–60 min. After the reaction, the catalyst could be recycled and reused. A possible mechanism to account for the tandem reaction is proposed. .

  一种新型的基本离子液体，即含有Brønsted碱和Lewis碱位点的1-(2-氨基乙基)吡啶鎓氢氧化物，已被用作合成2-氨基-4-苯基-6-(苯硫基)-3,5-二氰基吡啶的高效催化剂。在水-乙醇体系中进行的醛、丙二腈和硫醇的缩合与氧化串联反应，在30-60分钟内获得了合理至良好的产率。反应结束后，催化剂可以回收并重复使用。提出了一个可能的机制来解释串联反应。
• Facile and Rapid Access to Poly Functionalized Pyridine Derivatives
  作者：Pravin V. Shinde、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.1002/cjoc.201190178

  日期：2011.5

  An efficient and greener protocol for the synthesis of poly functionalized pyridines using tetra‐n‐butyl ammonium fluoride (TBAF) in water is established. Remarkable advantages of the present synthetic strategy over the others are shorter reaction times, higher isolated yields, reuse of catalytic system, simple work‐up procedure and more especially its applicability to heteryl and aliphatic aldehydes

  建立了在水中使用四正丁基氟化铵（TBAF）合成多官能吡啶的高效，绿色方案。与其他方法相比，本合成策略的显着优势是反应时间更短，分离产率更高，催化体系可重复使用，后处理步骤简单，尤其是适用于杂醛和脂族醛。
• Boric acid catalyzed convenient synthesis of 2-amino-3,5-dicarbonitrile-6-thio-pyridines in aqueous media
  作者：Pravin V. Shinde、Swapnil S. Sonar、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.1016/j.tetlet.2009.12.146

  日期：2010.3

  A one-pot three-component condensation of an aldehyde, malononitrile, and thiophenol has been achieved by conventional and ultrasound method. The reaction has been catalyzed by boric acid in aqueous medium. This protocol afforded corresponding 2-amino-3,5-dicarbonitrile-6-thio-pyridines in shorter reaction times and high yields with the green aspects by avoiding toxic catalysts and solvents.

  醛，丙二腈和苯硫酚的一锅三组分缩合已通过常规和超声方法实现。该反应已在含水介质中被硼酸催化。通过避免有毒的催化剂和溶剂，该方案以较短的反应时间和高收率在绿色方面提供了相应的2-氨基-3,5-二碳腈-6-硫代吡啶。
• K2CO3 catalyzed green and rapid access to 2-amino-3,5-dicarbonitrile-6-thio-pyridines
  作者：Mazaahir Kidwai、Ritika Chauhan

  DOI：10.1007/s13738-013-0368-4

  日期：2014.8

  A series of 2-amino-3,5-dicarbonitrile-6-thio-pyridine derivatives have been synthesized by a simple method via a one-pot, three-component condensation reaction of aromatic aldehydes and malononitrile with substituted thiophenols using potassium carbonate as a green base in polyethylene glycol (PEG-400) as a reusable solvent. This protocol proved to be efficient and environmentally benign in terms of high yields, short reaction times, mild conditions, and reusability of the reaction medium. .

  以碳酸钾为原料，通过芳香醛、丙二腈与取代苯硫酚的一锅三组分缩合反应，简单合成了一系列2-氨基-3,5-二甲腈-6-硫代吡啶衍生物。聚乙二醇 (PEG-400) 中的绿色碱作为可重复使用的溶剂。该方案在产率高、反应时间短、条件温和以及反应介质的可重​​复使用性方面被证明是高效且环境友好的。 。