2-<5-<1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-7-(phenylamino)pyrimido<4,5-d>pyrimidinyl>>benzonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-<5-<1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-7-(phenylamino)pyrimido<4,5-d>pyrimidinyl>>benzonitrile
• 英文别名: 2-(7-Anilino-1,3-dimethyl-2,4-dioxopyrimido[4,5-d]pyrimidin-5-yl)benzonitrile
• 化学式: C₂₁H₁₆N₆O₂
• 分子量: 384.397
• InChiKey: HDVOJYZUIHYQQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3-二氮杂萘 以 硝基苯 、 乙腈 为溶剂， 反应 2.0h， 生成 2-<5-<1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-7-(phenylamino)pyrimido<4,5-d>pyrimidinyl>>benzonitrile
  参考文献：
  名称：

  Reactions of uracils. 21. Zwitterionic heteropolycyclic uracils by a novel three-component reaction: iminophosphorane, isocyanate, heteroarene

  摘要：

  The novel three-component reaction of (uracil-6-ylimino)phosphorane 1, isocyanate 2, and (substituted) pyridines gives, in a one-pot procedure, a variety of new pyrido[ 1',2':3,41 pyrimido[4,5-d]pyrimidines 3-11. The zwitterionic ground state of these new ring systems is i.a. established by means of solvatochromism, Hammett correlations, NMR, and X-ray analysis. Replacement of the pyridine by isoquinoline and phthalazine gives access to the novel ring systems pyrimido[4',5':4,5]pyrimido-[6,1-a]isoquinoline and -phthalazine, which are formed as dihydro derivatives (14, 15) or as zwitterions (13,17), depending on there action conditions. Oxidative cleavage of the phthalazine 15 in nitrobenzene affords the pyrimido[4,5-d]pyrimidines 16.

  DOI：

  10.1021/jo00077a013

文献信息

• Wamhoff Heinrich, Schmidt Andreas, J. Org. Chem., 58 (1993) N 25, S 6976-6984
  作者：Wamhoff Heinrich, Schmidt Andreas

  DOI：——

  日期：——
• Reactions of uracils. 21. Zwitterionic heteropolycyclic uracils by a novel three-component reaction: iminophosphorane, isocyanate, heteroarene
  作者：Heinrich Wamhoff、Andreas Schmidt

  DOI：10.1021/jo00077a013

  日期：1993.12

  The novel three-component reaction of (uracil-6-ylimino)phosphorane 1, isocyanate 2, and (substituted) pyridines gives, in a one-pot procedure, a variety of new pyrido[ 1',2':3,41 pyrimido[4,5-d]pyrimidines 3-11. The zwitterionic ground state of these new ring systems is i.a. established by means of solvatochromism, Hammett correlations, NMR, and X-ray analysis. Replacement of the pyridine by isoquinoline and phthalazine gives access to the novel ring systems pyrimido[4',5':4,5]pyrimido-[6,1-a]isoquinoline and -phthalazine, which are formed as dihydro derivatives (14, 15) or as zwitterions (13,17), depending on there action conditions. Oxidative cleavage of the phthalazine 15 in nitrobenzene affords the pyrimido[4,5-d]pyrimidines 16.