5,6-diamino-8-diethylamino-2-phenyl-1,2-dihydrofuro[2,3-c]-2,7-naphthyridine-9-carbonitrile | 757221-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5,6-diamino-8-diethylamino-2-phenyl-1,2-dihydrofuro[2,3-c]-2,7-naphthyridine-9-carbonitrile
• 英文别名: 5,6-Diamino-8-(diethylamino)-2-phenyl-1,2-dihydrofuro[2,3-c][2,7]naphthyridine-9-carbonitrile
• CAS: 757221-25-3
• 化学式: C₂₁H₂₂N₆O
• 分子量: 374.445
• InChiKey: LRRHINCDBOIOHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5,6-diamino-8-diethylamino-2-phenyl-1,2-dihydrofuro[2,3-c]-2,7-naphthyridine-9-carbonitrile 、 环己酮 反应 2.0h， 以87%的产率得到2-diethylamino-9-phenyl-5,6,9,10-tetrahydro-4H-spiro{furo[2,3-c]pyrimido[4,5,6-ij]-2,7-naphthyridine-5,1'-cyclohexane}-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：

  氧化苯乙烯 、 2-amino-4-(cyanomethyl)-6-(diethylamino)-3,5-pyridinedicarbonitrile 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以79%的产率得到5,6-diamino-8-diethylamino-2-phenyl-1,2-dihydrofuro[2,3-c]-2,7-naphthyridine-9-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

文献信息

• 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.