1,3-dimethyl-5-hydroxy-8-phenyl-1,2,3,4,7,8-hexahydropyrido<2,3-d>pyrimidine-2,4,7-trione | 137278-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 1,3-dimethyl-5-hydroxy-8-phenyl-1,2,3,4,7,8-hexahydropyrido<2,3-d>pyrimidine-2,4,7-trione
• 英文别名: 5-hydroxy-1,3-dimethyl-8-phenyl-pyrido<2,3-d>pyrimidine-2,4,7-trione；5-hydroxy-1,3-dimethyl-8-phenyl-pyrido[2,3-d]pyrimidine-2,4,7-trione；5-hydroxy-1,3-dimethyl-8-phenylpyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione；5-hydroxy-1,3-dimethyl-8-phenylpyrido[2,3-d]pyrimidine-2,4,7-trione
• CAS: 137278-09-2
• 化学式: C₁₅H₁₃N₃O₄
• mdl: MFCD00219562
• 分子量: 299.286
• InChiKey: WUYOIBOBJDOTID-UHFFFAOYSA-N

物化性质

• 沸点：
  395.4±52.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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 4,6,14-Trimethyl-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
• 作为产物：
  描述：

  5-cyanoacetyl-6-phenylaminouracil 在 氢溴酸 作用下， 反应 0.5h， 以92%的产率得到1,3-dimethyl-5-hydroxy-8-phenyl-1,2,3,4,7,8-hexahydropyrido<2,3-d>pyrimidine-2,4,7-trione
  参考文献：
  名称：

  吡啶并[2,3-d]嘧啶4.氧代（羟基）吡啶并[2,3-d]嘧啶的合成及一些转化

  摘要：

  DOI：

  10.1007/bf00474003

文献信息

• Ring closure reactions of 5-azidopyrido[2,3-<i>d</i>]pyrimidinetriones to isoxazolo- and oxadiazolopyrido[2,3-<i>d</i>]pyrimidinetriones
  作者：Dang Van Tinh、Wolfgang Stadlbauer

  DOI：10.1002/jhet.5570450621

  日期：2008.11

  Thermal decomposition of 5-azidopyrido[2,3-d]pyrimidines 2 and 7 having reactive ortho-substituents such as a formyl or a nitro group yielded isoxazolo[3′,4′:4,5]pyrido[2,3-d]pyrimidines 3 or oxadiazolo-[3′,4′:4,5]pyrido[2,3-d]pyrimidines 9. The reaction conditions of the azide decomposition were studied by differential scanning calorimetry (DSC). In addition, desoxygenation of N-oxides 9 to oxadiazoles

  具有反应性邻位取代基（如甲酰基或硝基）的5-叠氮基吡啶并[2,3 - d ]嘧啶2和7的热分解生成异恶唑并[3'，4'：4,5]吡啶并[2,3- d ]嘧啶3或恶二唑-[3'，4'：4,5]吡啶[2,3- d ]嘧啶9.通过差示扫描量热法（DSC）研究了叠氮化物分解的反应条件。另外，研究了将N-氧化物9脱氧为恶二唑10和将叠氮化物7区域选择性还原为胺8。
• Ring closure reactions of pyrido[2,3-<i>d</i>]pyrimidines to pyrano[2′,3′:4,5]- and oxazolo[5′,4′:4,5]pyrido[2,3-<i>d</i>]pyrimidines
  作者：Dang Van Tinh、Wolfgang Stadlbauer

  DOI：10.1002/jhet.5570450517

  日期：2008.9

  zinc in the presence of carboxylic acids/anhydrides gave 2-alkyloxazolo[5′,4′:4,5]pyrido[2,3-d]pyrimidines 4, which were ring-opened to 6-aminopyrido[2,3-d]pyrimidines 5, 6 and 7. Cyclization of 6-aminopyrido[2,3-d]pyrimidines 6 with benzoylchlorides 8 gave 2-aryloxazolo[5′,4′:4,5]pyrido[2,3-d]pyrimidines 9. Reaction conditions for the cyclization have been studied by differential scanning calorimetry

  5-羟基-吡啶并[2,3- d ]嘧啶1与丙二酸酯的环缩合反应得到吡喃并[2'，3'：4,5]-吡啶并[2,3- d ]嘧啶2。硝化1并在羧酸/酸酐存在下用锌还原得到2-烷基恶唑并[5'，4'：4,5]吡啶[2,3- d ]嘧啶4，将其开环成6-氨基吡啶[2，3- d ]嘧啶5、6和7。6-氨基吡啶并[2,3- d ]嘧啶6与苯甲酰氯8的环化反应生成2-芳基恶唑并[5'，4'：4,5]吡啶并[2,3- d ]嘧啶9。通过差示扫描量热法（DSC）已经研究了用于环化的反应条件。
• Pyrido[2,3-d]pyrimidines Reactions of hydroxypyrido[2,3-d]pyrimidines with thionyl chloride in the presence of DMF
  作者：O. A. Burova、N. M. Smirnova、T. S. Safonova

  DOI：10.1007/bf00531483

  日期：1992.9
• Pyrido[2,3-d]pyrimidines 4. Synthesis and some transformations of oxo(hydroxy)pyrido[2,3-d]pyrimidines
  作者：O. A. Burova、N. M. Smirnova、V. I. Pol'shakov、G. S. Chernov、G. A. Losev、T. S. Safonova

  DOI：10.1007/bf00474003

  日期：1991.5
• 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.