2,3-dimethoxy-8-oxo-11-phenyl-5,6,8,11-tetrahydropyrazolo[3',4':4,5]pyrido[2,1-a]isoquinoline-12-carbonitrile | 1426390-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,3-dimethoxy-8-oxo-11-phenyl-5,6,8,11-tetrahydropyrazolo[3',4':4,5]pyrido[2,1-a]isoquinoline-12-carbonitrile
• 英文别名: 4,5-Dimethoxy-11-oxo-15-phenyl-10,14,15-triazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(17),2,4,6,12(16),13-hexaene-17-carbonitrile；4,5-dimethoxy-11-oxo-15-phenyl-10,14,15-triazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(17),2,4,6,12(16),13-hexaene-17-carbonitrile
• CAS: 1426390-76-2
• 化学式: C₂₃H₁₈N₄O₃
• 分子量: 398.421
• InChiKey: NFGSMNCVXMHWNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  80.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3,4-dihydro-6,7-dimethoxyisoquinolin-1-yl)acetonitrile 在 吡啶 、 三氯氧磷 作用下， 以 乙醇 、 硝基苯 、 邻二氯苯 为溶剂， 反应 31.0h， 生成 2,3-dimethoxy-8-oxo-11-phenyl-5,6,8,11-tetrahydropyrazolo[3',4':4,5]pyrido[2,1-a]isoquinoline-12-carbonitrile
  参考文献：
  名称：

  Synthesis and Reactivity of 2-Chloro-3-formylpyrido[2,1-a]isoquinoline Derivative. A Novel Routes to Pyrazolo[3',4':4,5]pyrido[2,1-a]isoquinoline and Isoquinolino[2,1-g][1,6]naphthyridines

  摘要：

  Treatment of 2-hydroxy-9,10-dimethoxy-4-oxo-6,7-dihydro-4H-pyrido[2,1-a]isoquinoline-1-carbonitrile 2 with POCl3/DMF gave 2-chloro-3-formylpyrido[2,1-a]isoquinoline derivative 3. Compound 3 reacted with hydrazines 5a-d to give the condensation products 6a-d. Cyclization of 6a gave pyrazolo[3',4':4,5]pyrido[2,1-a]isoquinoline derivative 7. Treatment of 3 with ethoxycarbonylmethylenetriphenylphosphorane 10 afforded (E)-ethyl 3-(2-chloro-1-cyano-9,10-dimethoxy-4-oxo-6,7-dihydro-4H-pyrido[2,1-a]isoquinolin-3-yl)acrylate 11. Azidation of 11 yielded the corresponding azido compound 12 Reduction of 12 gave the corresponding amino compound 13 which upon cyclization gave the novel tetracyclic product 14. Compound 12 reacted with triphenylphosphine to give phosphorane compound 15, which reacted with phenyl isothiocyanate to give a novel isoquinolino[2,1-g][1,6]naphthyridine derivative 18. Refluxing of 11 with amines 19a-c and thiophenols 22a-d in ethanol produced the corresponding substitution products 20a-c and 23a-d, respectively. Cyclization of 20a afforded isoquinolino[2,1-g][1,6]naphthyridine derivative 21.

  DOI：

  10.3987/com-12-12572

文献信息

• Synthesis and Reactivity of 2-Chloro-3-formylpyrido[2,1-a]isoquinoline Derivative. A Novel Routes to Pyrazolo[3',4':4,5]pyrido[2,1-a]isoquinoline and Isoquinolino[2,1-g][1,6]naphthyridines
  作者：Hamdi M. Hassaneen、Wagnat W. Wardkhan、Yasmin Sh. Mohammed

  DOI：10.3987/com-12-12572

  日期：——

  Treatment of 2-hydroxy-9,10-dimethoxy-4-oxo-6,7-dihydro-4H-pyrido[2,1-a]isoquinoline-1-carbonitrile 2 with POCl3/DMF gave 2-chloro-3-formylpyrido[2,1-a]isoquinoline derivative 3. Compound 3 reacted with hydrazines 5a-d to give the condensation products 6a-d. Cyclization of 6a gave pyrazolo[3',4':4,5]pyrido[2,1-a]isoquinoline derivative 7. Treatment of 3 with ethoxycarbonylmethylenetriphenylphosphorane 10 afforded (E)-ethyl 3-(2-chloro-1-cyano-9,10-dimethoxy-4-oxo-6,7-dihydro-4H-pyrido[2,1-a]isoquinolin-3-yl)acrylate 11. Azidation of 11 yielded the corresponding azido compound 12 Reduction of 12 gave the corresponding amino compound 13 which upon cyclization gave the novel tetracyclic product 14. Compound 12 reacted with triphenylphosphine to give phosphorane compound 15, which reacted with phenyl isothiocyanate to give a novel isoquinolino[2,1-g][1,6]naphthyridine derivative 18. Refluxing of 11 with amines 19a-c and thiophenols 22a-d in ethanol produced the corresponding substitution products 20a-c and 23a-d, respectively. Cyclization of 20a afforded isoquinolino[2,1-g][1,6]naphthyridine derivative 21.