2,4-diamino-5-(4-methylphenylsulfanyl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile | 1373941-20-8

• 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: 2,4-diamino-5-(4-methylphenylsulfanyl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile
• 英文别名: 2,4-diamino-5-(4-methylphenyl)sulfanyl-5H-chromeno[2,3-b]pyridine-3-carbonitrile
• CAS: 1373941-20-8
• 化学式: C₂₀H₁₆N₄OS
• 分子量: 360.439
• InChiKey: YHASZHKDZARYOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  水杨醛 、 4-甲苯硫酚 、 丙二腈 在 tin(II) oxide 作用下， 以 乙醇 为溶剂， 反应 0.95h， 以85%的产率得到2,4-diamino-5-(4-methylphenylsulfanyl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile
  参考文献：
  名称：

  SnO纳米颗粒可作为一锅合成chromeno [2,3- b ]吡啶和2-氨基-3,5-二氰基-6-硫烷基吡啶的有效催化剂†

  摘要：

  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。

  DOI：

  10.1039/c4ra04769a

文献信息

• 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
• Efficient synthesis of chromenopyridine and chromene via MCRs
  作者：Hai-Feng Gan、Wei-Wei Cao、Zheng Fang、Xin Li、Shi-Gui Tang、Kai Guo

  DOI：10.1016/j.cclet.2014.05.008

  日期：2014.10

  MCRs for preparation of chromenopyridines under reflux conditions and chromenes at room temperature conditions from different salicylaldehydes, malononitrile and different thiols (mol ratio = 1:2:1) were established. Mechanistic investigation suggests that the MCRs undergo different pathways at different temperatures and catalyzed by different organic bases. The structure of chromenopyridine and chromene are confirmed by crystal X-ray crystallography. (C) 2014 Kai Guo. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• K₂CO₃-Mediated, One-Pot, Multicomponent Synthesis of Medicinally Potent Pyridine and Chromeno[2,3-b]pyridine Scaffolds
  作者：Sarita Mishra、Rina Ghosh

  DOI：10.1080/00397911.2011.555284

  日期：2012.8.1

  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.
• 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].