2-amino-4-(3-nitrophenyl)-6-(phenylthio)pyridine-3,5-dicarbonitrile | 1019060-90-2

• 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-(3-nitrophenyl)-6-(phenylthio)pyridine-3,5-dicarbonitrile
• 英文别名: 2-Amino-4-(3-nitrophenyl)-6-phenylsulfanylpyridine-3,5-dicarbonitrile
• CAS: 1019060-90-2
• 化学式: C₁₉H₁₁N₅O₂S
• 分子量: 373.395
• InChiKey: LOPQVWYVGODWGL-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：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 potassium permanganate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.42h， 生成 2-amino-4-(3-nitrophenyl)-6-(phenylthio)pyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  K₂CO₃-Mediated, One-Pot, Multicomponent Synthesis of Medicinally Potent Pyridine and Chromeno[2,3-b]pyridine Scaffolds

  摘要：

  An efficient one-pot, multicomponent synthesis of 3,5-dicyanopyridines has been developed from the reaction of malononitrile and different thiophenol or thiols with a variety of aldehydes (aromatic including hindered ones, heteroaromatic, and aliphatic) in the presence of 20 mol% of K2CO3 in refluxing 50% aqeuous ethanol. KMnO4 has been utilized as a readily available, inexpensive oxidant for the in situ transformation of the initially formed dihydropyridine intermediate. K2CO3 also mediates the one-pot formation of chromeno[2,3-b]pyridines from reaction of salicylaldehyde or its analogs with malononitrile and thiol or thiophenols. Both of these conditions also work equally well under 50-fold scale-up conditions.Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.555284

文献信息

• 室温合成多取代吡啶类化合物的方法
  申请人：盐城师范学院

  公开号：CN107628992A

  公开（公告）日：2018-01-26

  本发明公开了室温合成多取代吡啶类化合物的方法。其技术关键是采用乙二胺/三硝基甲烷低共熔体为催化剂，乙醇水溶液为反应介质，以芳香醛、丙二氰、苯硫酚为原料，在常温、常压下合成该目标化合物。优点为：(1)原料来源广泛，制备方便；(2)催化剂催化效果好，分离简单，可循环使用、节能减排的效果明显；(3)反应在常温常压下进行，安全平稳，容易工业放大，是环境友好的化工过程。
• SnO nanoparticles as an efficient catalyst for the one-pot synthesis of chromeno[2,3-b]pyridines and 2-amino-3,5-dicyano-6-sulfanyl pyridines
  作者：Javad Safaei-Ghomi、Hossein Shahbazi-Alavi、Elham Heidari-Baghbahadorani

  DOI：10.1039/c4ra04769a

  日期：——

  SnO nanoparticles have been used as an efficient catalyst for the preparation of chromeno[2,3-b]pyridines and 2-amino-3,5-dicyano-6-sulfanyl pyridines under reflux conditions in ethanol in good to excellent yields. This flexible and nano-catalytic procedure showed good recyclability and provides a clean condensation reaction in a short reaction time.

  SnO纳米颗粒已被用作高效的催化剂，用于在乙醇中回流条件下以良好至极好的收率制备苯并[2,3- b ]吡啶和2-氨基-3,5-二氰基-6-硫烷基吡啶。这种灵活的纳米催化程序显示出良好的可回收性，并在较短的反应时间内提供了干净的缩合反应。
• Borax catalyzed domino reactions: synthesis of highly functionalised pyridines, dienes, anilines and dihydropyrano[3,2-c]chromenes
  作者：Aniruddha Molla、Sahid Hussain

  DOI：10.1039/c4ra03627a

  日期：——

  Borax, an innocuous, inexpensive, and a naturally occurring material, very efficiently catalyzes the Knoevenagel condensation and Michael addition in domino fashion for the construction of highly functionalised pyridines, dienes, anilines and dihydropyrano[3,2-c]chromenes. The present protocol offers advantages in terms of higher yields, wide scope of substrates, operational simplicity, short reaction time, no requirement of workup or column chromatography, and easy access to a wide range of structurally diverse functionalized molecules of biological importance. Recycling of the catalyst and scaling up of the reactions are important attributes of this catalytic process.

  硼砂是一种无害、廉价且自然存在的物质，它以串联方式高效催化Knoevenagel缩合反应和Michael加成反应，用于构建高度功能化的吡啶、二烯、苯胺和二氢吡喃[3,2-c]色烯结构。目前的协议在产量、底物范围广度、操作简便性、反应时间短、无需后处理或柱层析以及易于获得结构多样且具有生物学意义的官能化分子等方面具有优势。催化剂的回收和反应的规模放大是该催化过程的重要特点。
• 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）。
• Application of novel and reusable Fe₃O₄@Co^II(macrocyclic Schiff base ligand) for multicomponent reactions of highly substituted thiopyridine and 4<i>H</i>‐chromene derivatives
  作者：Hakimeh Ebrahimiasl、Davood Azarifar、Jamshid Rakhtshah、Hassan Keypour、Masoumeh Mahmoudabadi

  DOI：10.1002/aoc.5769

  日期：2020.9

  elemental analysis (CHNS). Then, the catalytic performance was successfully investigated in the multicomponent synthesis of 2‐amino‐4‐aryl‐6‐(phenylsulfanyl)pyridine‐3,5‐dicarbonitrile and 2‐amino‐5,10‐dioxo‐4‐aryl‐5,10‐dihydro‐4H‐benzo[g]chromene‐3‐carbonitrile derivatives. Furthermore, the catalyst was isolated using a simple filtration, and recovery of the nanocatalyst was demonstrated five times without

  在本研究中，我们设计并合成了固定在Fe 3 O 4上的Co II（含有1,4-二氮杂pan的大环席夫碱配体）纳米颗粒作为新型，可回收和非均相的催化剂。使用傅立叶变换红外光谱，扫描电子显微镜，透射电子显微镜，X射线衍射，能量色散X射线光谱，热重分析，振动样品磁力分析，差分反射光谱，Brunauere-Emmette等多种技术对纳米材料进行了全面表征–Teller方法，电感耦合等离子体和元素分析（CHNS）。然后，在2-氨基-4-芳基-6（苯硫基）吡啶-3,5-二腈和2-氨基-5,10-二氧代-4-芳基-5的多组分合成中成功地研究了催化性能。 10-二氢-4 H-苯并[ g] chromene-3-腈衍生物。此外，使用简单的过滤分离了催化剂，并且证实了纳米催化剂的回收五次而没有任何活性损失。