2-amino-4-(cyanomethyl)-6-(diethylamino)-3,5-pyridinedicarbonitrile | 380638-39-1

• 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-(cyanomethyl)-6-(diethylamino)-3,5-pyridinedicarbonitrile
• 英文别名: 3,5-Pyridinedicarbonitrile, 2-amino-4-(cyanomethyl)-6-(diethylamino)-；2-amino-4-(cyanomethyl)-6-(diethylamino)pyridine-3,5-dicarbonitrile
• CAS: 380638-39-1
• 化学式: C₁₃H₁₄N₆
• 分子量: 254.294
• InChiKey: XRZHRSJWIHMKKY-UHFFFAOYSA-N

物化性质

• 沸点：
  531.9±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-4-(cyanomethyl)-6-(diethylamino)-3,5-pyridinedicarbonitrile 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-diethylamino-5-methyl-9-phenyl-9,10-dihydro-4H-furo[2,3-c]pyrimido[4,5,6-ij]-2,7-naphthyridine-1-carbonitrile
  参考文献：
  名称：

  Synthesis of furo[2,3-c]-2,7-naphthyridine derivatives via domino heterocyclization reaction

  摘要：

  2-Amino-4-cyanomethyl-6-dialkylamino-3,5-pyridinedicarbonitriles were found to react with substituted oxiranes yielding 5,6-diamino-8-dialkylamino-1,2-dihydrofuro [2,3-c]-2,7-naphthyridine-9-carbonitriles. The oxirane ring was shown to be opened selectively from the unsubstituted side and further cyclization occurred with participation of 3-CN, but not 5-CN of the starting pyridines. The furonaphthyridines obtained were converted into 2-dialkylamino-5-methyl-9,10-dihydro-4H-furo[2,3-c]pyrimido[4,5,6-ij]-2,7-naphthyridine-l-carbonitriles and 2-dialkylamino-5,6,9,10-tetrahydro-4H-spiroffuro[2,3-c]pyrimido[4,5,6-ij]-2,7-naphthyridine-5,1'-cyclohexane}1-carbonitriles by treatment with acetic anhydride and cyclohexanone, respectively. The structure of prepared compounds was confirmed unambiguously by X-ray crystallographic study. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.074
• 作为产物：
  描述：

  2-氨基-6-氯-4-(氰基甲基)吡啶-3,5-二甲腈 、 二乙胺 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以97%的产率得到2-amino-4-(cyanomethyl)-6-(diethylamino)-3,5-pyridinedicarbonitrile
  参考文献：
  名称：

  Regioselective Heteroannelation in 4-Cyanomethyl-3,5-pyridinedicarbonitriles. Synthesis of 6-Alkoxy-3-dialkylamino-1,8-diamino-2,7-naphthyridine-4-carbonitriles

  摘要：

  The title naphthyridines were found to be the sole products obtained after treatment of 2-amino-4-cyanomethyl-6-dialkylamino-3,5-pyridinedicarbonitriles with alkoxides. The starting pyridine derivatives were prepared by amination of the readily available 2-amino-6-chloro-4-cyanomethyl-3,5-pyridinedicarbonitrile in quantitative yields.

  DOI：

  10.1007/s00706-003-0006-4

文献信息

• Synthesis of pyrrolo[2,3-c]2,7-naphthyridine derivatives by cascade heterocyclization reaction of 2-amino-4-cyanomethyl-6-dialkylamino-3,5-pyridinedicarbonitriles
  作者：Anton V Tverdokhlebov、Elizaveta V Resnyanska、Alexander V Zavada、Andrey A Tolmachev、Alexander N Kostyuk、Alexander N Chernega

  DOI：10.1016/j.tet.2004.05.007

  日期：2004.6

  naphthyridine derivatives with acetic acid anhydride and cyclohexanone yielded 2-dialkylamino-6,8,9,10-tetrahydro-5-methyl-9-oxopyrimido[4,5,6-ij]pyrrolo[2,3-c]2,7-naphthyridine-1-carbonitriles and 2-dialkylamino-4,5,6,8,9,10-hexahydro-9-oxospiropyrimido[4,5,6-ij]pyrrolo[2,3-c]2,7-naphthyridine-5,1′-cyclohexane}-1-carbonitriles, respectively. All fused 2,7-naphthyridines obtained were derivatives of novel

  发现标题吡啶二腈与N-取代的氯乙酰胺烷基化，得到5,6-二氨基-8-二烷基氨基-2,3-二氢-2-氧代-1 H-吡咯并[2,3 - c ] 2,7-萘啶-9-腈。通过X射线晶体学研究清楚地证实了所获得的化合物的结构。杂环反应进行区域选择性地涉及起始吡啶的3-CN基团，而没有5-CN参与。讨论了选择性的原因。制备的萘啶衍生物与乙酸酐和环己酮的相互作用产生2-二烷基氨基-6,8,9,10-四氢-5-甲基-9-氧嘧啶基[4,5,6- ij ]吡咯并[2,3- c] 2,7-萘啶-1-腈和2-二烷基氨基-4,5,6,8,9,10-六氢-9-氧杂螺pyrimido [4,5,6- ij ] pyrrolo [2,3- c分别为] 2,7-萘啶-5,1'-环己烷} -1-腈。获得的所有稠合的2,7-萘啶均为新型杂环系统的衍生物。
• Regioselective Heteroannelation in 4-Cyanomethyl-3,5-pyridinedicarbonitriles. Synthesis of 6-Alkoxy-3-dialkylamino-1,8-diamino-2,7-naphthyridine-4-carbonitriles
  作者：Anton V. Tverdokhlebov、Elizaveta V. Resnyanska、Andrey A. Tolmachev、Alexander V. Zavada

  DOI：10.1007/s00706-003-0006-4

  日期：2003.6

  The title naphthyridines were found to be the sole products obtained after treatment of 2-amino-4-cyanomethyl-6-dialkylamino-3,5-pyridinedicarbonitriles with alkoxides. The starting pyridine derivatives were prepared by amination of the readily available 2-amino-6-chloro-4-cyanomethyl-3,5-pyridinedicarbonitrile in quantitative yields.
• Synthesis of furo[2,3-c]-2,7-naphthyridine derivatives via domino heterocyclization reaction
  作者：Anton V. Tverdokhlebov、Alexander V. Zavada、Andrey A. Tolmachev、Alexander N. Kostyuk、Alexander N. Chernega、Eduard B. Rusanov

  DOI：10.1016/j.tet.2005.07.074

  日期：2005.10

  2-Amino-4-cyanomethyl-6-dialkylamino-3,5-pyridinedicarbonitriles were found to react with substituted oxiranes yielding 5,6-diamino-8-dialkylamino-1,2-dihydrofuro [2,3-c]-2,7-naphthyridine-9-carbonitriles. The oxirane ring was shown to be opened selectively from the unsubstituted side and further cyclization occurred with participation of 3-CN, but not 5-CN of the starting pyridines. The furonaphthyridines obtained were converted into 2-dialkylamino-5-methyl-9,10-dihydro-4H-furo[2,3-c]pyrimido[4,5,6-ij]-2,7-naphthyridine-l-carbonitriles and 2-dialkylamino-5,6,9,10-tetrahydro-4H-spiroffuro[2,3-c]pyrimido[4,5,6-ij]-2,7-naphthyridine-5,1'-cyclohexane}1-carbonitriles by treatment with acetic anhydride and cyclohexanone, respectively. The structure of prepared compounds was confirmed unambiguously by X-ray crystallographic study. (c) 2005 Elsevier Ltd. All rights reserved.