5-((furan-2-yl) methylthio)-2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-((furan-2-yl) methylthio)-2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitrile
• 英文别名: 2,4-diamino-5-(furan-2-ylmethylsulfanyl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile
• 化学式: C₁₈H₁₄N₄O₂S
• 分子量: 350.401
• InChiKey: GXVCQBUXGNLHEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  糠基硫醇 、 水杨醛 、 丙二腈 在 chitosan functionalized by citric acid CS(at)CA 作用下， 以 乙醇 为溶剂， 反应 0.67h， 以85%的产率得到5-((furan-2-yl) methylthio)-2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitrile
  参考文献：
  名称：

  柠檬酸功能化壳聚糖：一锅合成 2,4-diamino-5H-[1]benzopyrano[2,3-b]pyridine-3-carbonitriles 5-(arylthio) or 5-[(arylmethyl) 的有效催化剂)硫代]取代

  摘要：

  摘要 柠檬酸官能化壳聚糖 (CS) 已用作制备 2,4-二氨基-5H-[1] 苯并吡喃并 [2,3-b] 吡啶-3-甲腈 5-(芳硫基) 或5-[(芳甲基)硫代]被水杨醛、硫醇和2当量的多组分反应取代。在乙醇中回流条件下的丙二腈。使用简单易得的起始材料、短时间内高产率、催化剂的可重复使用性和很少的催化剂负载是该协议的一些重要特征。通过红外光谱 (FT-IR)、X 射线衍射、热重分析和差示扫描量热法证实了柠檬酸官能化的 CS 的结构。图形概要

  DOI：

  10.1080/17415993.2016.1275633

文献信息

• 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。
• Convenient one-step synthesis of a medicinally relevant benzopyranopyridine system
  作者：Nikolai M. Evdokimov、Artem S. Kireev、Andrey A. Yakovenko、Mikhail Yu. Antipin、Igor V. Magedov、Alexander Kornienko

  DOI：10.1016/j.tetlet.2006.10.110

  日期：2006.12

  Benzopyrano[2,3-b]pyridine is an important privileged medicinal scaffold. A three-component reaction of salicylaldehydes, thiols and 2 equiv of malononitrile that leads to the formation of a series of compounds incorporating 2,4-diamino-3-cyano-5-sulfanylbenzopyrano[2,3-b]pyridine framework is described. A proposed mechanism with the supporting experimental data is presented.

  苯并吡喃[2,3-b]吡啶是一种重要的特权药用支架。描述了水杨醛、硫醇和 2 当量丙二腈的三组分反应，导致形成一系列包含 2,4-二氨基-3-氰基-5-硫烷基苯并吡喃 [2,3-b] 吡啶骨架的化合物。提出了一种具有支持实验数据的机制。
• Highly efficient synthesis of benzopyranopyridines via ZrP₂O₇nanoparticles catalyzed multicomponent reactions of salicylaldehydes with malononitrile and thiols
  作者：Javad Safaei-Ghomi、Marzieh Kiani、Abolfazl Ziarati、Hossein Shahbazi-Alavi

  DOI：10.1080/17415993.2014.913291

  日期：2014.7.4

  ZrP2O7 nanoparticles as an efficient catalyst have been used for the preparation of benzopyrano[2,3-b]pyridines from the four-component condensation reaction of salicylalde-hydes, thiols, and 2 equiv. of malononitrile under reflux conditions in ethanol in excellent yields and short reaction times.[GRAPHICS].
• One-Step Synthesis of Heterocyclic Privileged Medicinal Scaffolds by a Multicomponent Reaction of Malononitrile with Aldehydes and Thiols
  作者：Nikolai M. Evdokimov、Artem S. Kireev、Andrey A. Yakovenko、Mikhail Yu. Antipin、Igor V. Magedov、Alexander Kornienko

  DOI：10.1021/jo070114u

  日期：2007.4.1

  Heterocyclic privileged medicinal scaffolds involving pyridine, 1,4-dihydropyridine, chromeno[2,3-b]pyridine, and dihydro-1,4-dithiepine frameworks are prepared via a single-step multicomponent reaction of structurally diverse aldehydes with various thiols and malononitrile. Mechanistic studies of the synthetic pathway leading to pyridines reveal that 1,4-dihydropyridines undergo oxidation by the intermediate Knoevenagel adducts rather than by air oxygen. The use of o,o'-disubstituted aromatic aldehydes leads to the corresponding 1,4-dihydropyridines, whereas salicylic aldehydes result in chromeno[2,3-b]pyridines. Reactions of ethanedithiol as a thiol component produce dimeric pyridines with sterically unencumbered aldehydes, while o,o'-disubstituted aromatic aldehydes give dihydro-1,4-dithiepines. Thus, depending on the aldehyde and thiol types, diverse libraries of medicinally relevant compounds can be prepared by a simple one-step process involving no chromatography.
• Chitosan functionalized by citric acid: an efficient catalyst for one-pot synthesis of 2,4-diamino-5<i>H</i>-[1]benzopyrano[2,3-<i>b</i>]pyridine-3-carbonitriles 5-(arylthio) or 5-[(arylmethyl)thio] substituted
  作者：Javad Safaei-Ghomi、Maryam Tavazo、Mohammad Reza Vakili、Hossein Shahbazi-Alavi

  DOI：10.1080/17415993.2016.1275633

  日期：2017.5.4

  ABSTRACT Chitosan (CS) functionalized by citric acid has been used as an efficient catalyst for the preparation of 2,4-diamino-5H-[1]benzopyrano[2,3-b]pyridine-3-carbonitriles 5-(arylthio) or 5-[(arylmethyl)thio] substituted by a multicomponent reaction of salicylaldehydes, thiols and 2 equiv. of malononitrile under reflux condition in ethanol. Use of simple and readily available starting materials

  摘要 柠檬酸官能化壳聚糖 (CS) 已用作制备 2,4-二氨基-5H-[1] 苯并吡喃并 [2,3-b] 吡啶-3-甲腈 5-(芳硫基) 或5-[(芳甲基)硫代]被水杨醛、硫醇和2当量的多组分反应取代。在乙醇中回流条件下的丙二腈。使用简单易得的起始材料、短时间内高产率、催化剂的可重复使用性和很少的催化剂负载是该协议的一些重要特征。通过红外光谱 (FT-IR)、X 射线衍射、热重分析和差示扫描量热法证实了柠檬酸官能化的 CS 的结构。图形概要