2,4-diamino-5-(4-chlorophenylsulfanyl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile | 1373941-19-5

• 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-chlorophenylsulfanyl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile
• 英文别名: 2,4-diamino-5-(4-chlorophenylthio)-5H-chromeno[2,3-b]pyridine-3-carbonitrile；2,4-diamino-5-(4-chlorophenyl)sulfanyl-5H-chromeno[2,3-b]pyridine-3-carbonitrile
• CAS: 1373941-19-5
• 化学式: C₁₉H₁₃ClN₄OS
• 分子量: 380.857
• InChiKey: OAFQPSQEOAQHMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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-氯苯硫酚 、 丙二腈 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 3.5h， 以67%的产率得到2,4-diamino-5-(4-chlorophenylsulfanyl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile
  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

• 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.
• 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.