14-Fluoro-4,6-dimethyl-8-phenyl-4,6,8,18-tetrazatetracyclo[8.8.0.02,7.012,17]octadeca-1(10),2(7),11,13,15,17-hexaene-3,5,9-trione | 177082-76-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 14-Fluoro-4,6-dimethyl-8-phenyl-4,6,8,18-tetrazatetracyclo[8.8.0.02,7.012,17]octadeca-1(10),2(7),11,13,15,17-hexaene-3,5,9-trione
• CAS: 177082-76-7
• 化学式: C₂₂H₁₅FN₄O₃
• 分子量: 402.385
• InChiKey: CKOHQSUEVQAQMR-UHFFFAOYSA-N

物化性质

• 沸点：
  608.5±65.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-dimethyl-5-hydroxy-8-phenyl-1,2,3,4,7,8-hexahydropyrido<2,3-d>pyrimidine-2,4,7-trione 在 sodium hydroxide 、 三氯氧磷 作用下， 反应 7.0h， 生成 14-Fluoro-4,6-dimethyl-8-phenyl-4,6,8,18-tetrazatetracyclo[8.8.0.02,7.012,17]octadeca-1(10),2(7),11,13,15,17-hexaene-3,5,9-trione
  参考文献：
  名称：

  Ring closure reaction of 5-hydroxy-pyrido[2,3-d]pyrimidine-2,4,7-triones to benzo[b]pyrimido[4,5-h]1,6-naphthyridine-1,3,6-triones

  摘要：

  N-Substituted aminouracils (1) react with malonates by cyclocondensation to 5-hydroxy-pyrido [2,3-d] pyrimidine-2,4,7-triones (2), which give with triethylorthoformate and aniline 6-(phenylaminomethylene)-pyrido[2,3-d]pyrimidine-tetraone (3). Halogenation of 2a-d (with R(2) = Me) with phosphorylchloride leads to 5,7-dichloro-pyrido [2,3-d]pyrimidine-2,4-diones (4) by cleavage of the methyl group at N-8, whereas Vilsmeier reaction of 2 affords 5-chloro-6-formyl derivatives (6), which cyclize with arylamines to give benzo[b]pyrimido[4,5-h] 1,6-naphthyridines (9). Compounds 9 were obtained independently by amination of the tosylates 5 to the 5-arylamino compounds 8, and Vilsmeier formylation to yield 9.

  DOI：

  10.1002/prac.19963380129

文献信息

• Ring closure reaction of 5-hydroxy-pyrido[2,3-d]pyrimidine-2,4,7-triones to benzo[b]pyrimido[4,5-h]1,6-naphthyridine-1,3,6-triones
  作者：Ahmed F. A. Khattab、Dang Van Tinh、Wolfgang Stadlbauer

  DOI：10.1002/prac.19963380129

  日期：——

  N-Substituted aminouracils (1) react with malonates by cyclocondensation to 5-hydroxy-pyrido [2,3-d] pyrimidine-2,4,7-triones (2), which give with triethylorthoformate and aniline 6-(phenylaminomethylene)-pyrido[2,3-d]pyrimidine-tetraone (3). Halogenation of 2a-d (with R(2) = Me) with phosphorylchloride leads to 5,7-dichloro-pyrido [2,3-d]pyrimidine-2,4-diones (4) by cleavage of the methyl group at N-8, whereas Vilsmeier reaction of 2 affords 5-chloro-6-formyl derivatives (6), which cyclize with arylamines to give benzo[b]pyrimido[4,5-h] 1,6-naphthyridines (9). Compounds 9 were obtained independently by amination of the tosylates 5 to the 5-arylamino compounds 8, and Vilsmeier formylation to yield 9.