2-amino-6-(benzylsulfanyl)-4-(2,5-dimethoxyphenyl)-3,5-pyridinedicarbonitrile

• 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-6-(benzylsulfanyl)-4-(2,5-dimethoxyphenyl)-3,5-pyridinedicarbonitrile
• 英文别名: 2-Amino-6-benzylsulfanyl-4-(2,5-dimethoxyphenyl)pyridine-3,5-dicarbonitrile
• 化学式: C₂₂H₁₈N₄O₂S
• 分子量: 402.477
• InChiKey: KVSUYXWEHJCGEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 、 苄硫醇 、 丙二腈 在 1,4-dinitropyrazine-1,4-diium trinitromethanide 作用下， 以 neat (no solvent) 为溶剂， 反应 0.5h， 以89%的产率得到2-amino-6-(benzylsulfanyl)-4-(2,5-dimethoxyphenyl)-3,5-pyridinedicarbonitrile
  参考文献：
  名称：

  新型纳米结构二硝基吡嗪熔盐催化剂在端基氧化法合成磺胺吡啶中的应用

  摘要：

  1,4-二硝基吡嗪-1,4-二硝基三甲基甲烷{[1,4-吡嗪-NO 2 ] [C（NO 2）3 ] 2 }是一种新型的纳米结构熔融盐（NMS），催化2-氨基-的合成在室温下，无溶剂条件下，几种芳族醛，丙二腈和苄基硫醇之间通过一锅式三组分缩合反应生成3,5-二碳腈-6-磺酰胺基吡啶衍生物。FTIR，1 H NMR，13完全表征了合成的NMS催化剂CNMR，质量，热重，X射线衍射图，扫描电子显微镜和透射电子显微镜分析。所描述方法的主要优点是温和，易于分离，收率高和反应时间短。对于2-氨基-3,5-二碳腈-6-磺酰胺基吡啶合成的最后一步，提出了合理的机理。我们认为，拟议的机制有可能在将来纳入研究生教科书中。

  DOI：

  10.1007/s13738-017-1123-z

文献信息

• 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.
• One-Step, Three-Component Synthesis of Pyridines and 1,4-Dihydropyridines with Manifold Medicinal Utility
  作者：Nikolai M. Evdokimov、Igor V. Magedov、Artem S. Kireev、Alexander Kornienko

  DOI：10.1021/ol052994+

  日期：2006.3.2

  Privileged medicinal scaffolds based on the structures of 2-amino-3,5-dicyano-6-sulfanylpyridines and the corresponding 1,4-dihydropyridines have been prepared via a single-step, three-component reaction of structurally diverse aldehydes with various thiols and malononitrile. Mechanistic studies revealed that 1,4-dyhidropyridines undergo oxidation by the intermediate Knoevenagel adducts rather than by air oxygen. Although the latter process undermines the yields of pyridines, it results in the formation of substituted enaminonitriles, promising antiinflammatory agents.
• Application of novel nanostructured dinitropyrazine molten salt catalyst for the synthesis of sulfanylpyridines via anomeric based oxidation
  作者：Mohammad Ali Zolfigol、Maliheh Safaiee、Bahar Ebrahimghasri、Saeed Baghery、Saied Alaie、Mahya Kiafar、Avat Taherpour、Yadollah Bayat、Asiye Asgari

  DOI：10.1007/s13738-017-1123-z

  日期：2017.9

  trinitromethanide [1,4-pyrazine-NO2][C(NO2)3]2} as a novel nanostructured molten salt (NMS) catalyzed the synthesis of 2-amino-3,5-dicarbonitrile-6-sulfanylpyridine derivatives via the one-pot three-component condensation reaction between several aromatic aldehyde, malononitrile and benzyl mercaptan at room temperature under solvent-free conditions. The synthesized NMS catalyst was fully characterized by

  1,4-二硝基吡嗪-1,4-二硝基三甲基甲烷[1,4-吡嗪-NO 2 ] [C（NO 2）3 ] 2 }是一种新型的纳米结构熔融盐（NMS），催化2-氨基-的合成在室温下，无溶剂条件下，几种芳族醛，丙二腈和苄基硫醇之间通过一锅式三组分缩合反应生成3,5-二碳腈-6-磺酰胺基吡啶衍生物。FTIR，1 H NMR，13完全表征了合成的NMS催化剂CNMR，质量，热重，X射线衍射图，扫描电子显微镜和透射电子显微镜分析。所描述方法的主要优点是温和，易于分离，收率高和反应时间短。对于2-氨基-3,5-二碳腈-6-磺酰胺基吡啶合成的最后一步，提出了合理的机理。我们认为，拟议的机制有可能在将来纳入研究生教科书中。