5-<(4-Nitrophenyl)amino>-3-ethylpyrazolo<3',4':4,5>pyrimido<6,1-a>isoquinolinium betaine

• 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: 5-<(4-Nitrophenyl)amino>-3-ethylpyrazolo<3',4':4,5>pyrimido<6,1-a>isoquinolinium betaine
• 英文别名: 14-ethyl-N-(4-nitrophenyl)-10,12,14,15-tetrazatetracyclo[8.7.0.02,7.013,17]heptadeca-1(17),2,4,6,8,12,15-heptaen-11-imine
• 化学式: C₂₁H₁₆N₆O₂
• 分子量: 384.397
• InChiKey: ASGKBNZTCBMZSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  89.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异喹啉 、 异氰酸对硝基苯 、 5-<(Triphenylphosphoranylidene)amino>-1-ethylpyrazole 以 乙腈 为溶剂， 反应 3.0h， 以27%的产率得到5-<(4-Nitrophenyl)amino>-3-ethylpyrazolo<3',4':4,5>pyrimido<6,1-a>isoquinolinium betaine
  参考文献：
  名称：

  On the Synthesis of Zwitterionic Heteropolycyclic Pyrazoles by a Three-Component Reaction. Some Mechanistic Considerations

  摘要：

  The novel three-component reaction involving a heterocyclic iminophosphorane, an isocyanate, and a hetarene component is applied to an aromatic pyrazole iminophosphorane 1 and to an analogous pyrazolone derivative 13. The hitherto unknown zwitterionic pyrazolo[3,4':4,5]pyrimido[6,1-alpha]-isoquinolines 11a,b and 16a,b, pyrazolo[3',4':4,5]pyrimido[6,1-alpha]phthalazine 6b, and pyrazolo[3',4':4,5]pyrido[6,1-alpha]pyrimidines 15a,b are obtained. Additionally, the novel cycloaddition products with triazolinediones, the pyrazolo[3,4-e][1,2,4]triazolo[1,2-alpha] 1,2,4]triazinediones 9a,b, are described. The isolation of the dihydro compound 4 and the phthalazinium salt 5 supports a stepwise mechanism for the zwitterion formation. While the influence of the aromaticity of the iminophosphorane component appears to be negligible, the aromaticity of the hetarene component determines the limitations of this versatile reaction. X-ray structures of 11a, 5b, and 16b as well as UV-, MS-, and NMR-spectra and semiempirical calculations confirm the zwitterionic character of the reaction products.

  DOI：

  10.1021/jo00093a033

文献信息

• On the Synthesis of Zwitterionic Heteropolycyclic Pyrazoles by a Three-Component Reaction. Some Mechanistic Considerations
  作者：Heinrich Wamhoff、Christian Bamberg、Stefan Herrmann、Martin Nieger

  DOI：10.1021/jo00093a033

  日期：1994.7

  The novel three-component reaction involving a heterocyclic iminophosphorane, an isocyanate, and a hetarene component is applied to an aromatic pyrazole iminophosphorane 1 and to an analogous pyrazolone derivative 13. The hitherto unknown zwitterionic pyrazolo[3,4':4,5]pyrimido[6,1-alpha]-isoquinolines 11a,b and 16a,b, pyrazolo[3',4':4,5]pyrimido[6,1-alpha]phthalazine 6b, and pyrazolo[3',4':4,5]pyrido[6,1-alpha]pyrimidines 15a,b are obtained. Additionally, the novel cycloaddition products with triazolinediones, the pyrazolo[3,4-e][1,2,4]triazolo[1,2-alpha] 1,2,4]triazinediones 9a,b, are described. The isolation of the dihydro compound 4 and the phthalazinium salt 5 supports a stepwise mechanism for the zwitterion formation. While the influence of the aromaticity of the iminophosphorane component appears to be negligible, the aromaticity of the hetarene component determines the limitations of this versatile reaction. X-ray structures of 11a, 5b, and 16b as well as UV-, MS-, and NMR-spectra and semiempirical calculations confirm the zwitterionic character of the reaction products.