8-Methyl-4H-pyrido<1,2-a>pyrimidine-2,4-dione | 4742-77-2

• 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: 8-Methyl-4H-pyrido<1,2-a>pyrimidine-2,4-dione
• 英文别名: 8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-dione；8-methyl-pyrido[1,2-a]pyrimidine-2,4-dione；8-Methyl-pyrido[1,2-a]pyrimidin-2,4-dion；8-Methyl-2.3-dihydro-2-oxo-4H-pyrido<1.2-a>pyrimidin-4-on；8-Methyl-2,3-dihydro-4H-pyrido<1.2-a>pyrimidin-2,4-dion；8-Methyl-2.3-dihydro-4H-pyrido<1.2-a>pyrimidin-2.4-dion；8-Methylpyrido[1,2-a]pyrimidine-2,4-dione
• CAS: 4742-77-2
• 化学式: C₉H₈N₂O₂
• 分子量: 176.175
• InChiKey: YZEPPXWJRMSDLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-Methyl-4H-pyrido<1,2-a>pyrimidine-2,4-dione 、 4-羟基苯甲酰肼 、 原甲酸三乙酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以78%的产率得到4-hydroxy-N'-{[8-methyl-2,4-dioxo-2H-pyrido[1,2-a]pyrimidin-3(4H)-ylidene]methyl}benzohydrazide
  参考文献：
  名称：

  Synthesis, characterization, and urease inhibition of 5-substituted-8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-diones

  摘要：

  5-Substituted-8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-dione and its anilines, amino pyridines and hydrazides derivatives were prepared in a good to excellent yields. In the first step 8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-dione (1) was prepared by reacting 4-methyl-2-aminopyridine, with diethylmalonate. Compounds substituted pyrido[1,2-a]pyrimidine-2,4(3H)-diones (PPMDO) (2)-(17) were prepared by condensing 8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-dione in the presence of triethylorthoformte (TEF) and dimethylformamide (DMF), with respective amino components viz. 2-aminoacetophenone, 3-aminoacetophenone, 4-aminoacetophenone, 2,4,6-trimethylaniline, 2-fluoroaniline, 3-fluoroaniline, 4-fluoroaniline, 2-aminothiophenol, 2-amino-4-methylpyridine, 2-amino-5-methylpyridine, 2-amino-5-nitropyridine, Benzoic hydrazide, 4-nitrobenzoic hydrazide, 4-bromobenzoic hydrazide, 4-chlorobenzoic hydrazide and 4-hydroxybenzoic hydrazide, respectively. The chemical structures of all the compounds were elucidated by IR, H-1-NMR, C-13-NMR and elemental analysis data. The synthesized compounds were screened for their in vitro urease inhibition activity, by the phenol hypochlorite method. These compounds were found to exhibit either no or low to moderate or significant activity. The compounds (9) and (14) showed comparatively much higher activity. However, the compound (9) was found to be the most active one.

  DOI：

  10.1007/s00044-010-9491-2
• 作为产物：
  描述：

  2-氨基-4-甲基吡啶 、 2,4,6-三氯苯基马来酸二酯 以 丙酮 为溶剂， 以88%的产率得到8-Methyl-4H-pyrido<1,2-a>pyrimidine-2,4-dione
  参考文献：
  名称：

  Electro-organic reactions part 35. Efficient carbon—oxygen bond formation in the anodic coupling of pyridopyrimidine derivatives.

  摘要：

  4-H-Pyrido[1,2-a]pyrimidine-2,4-diones (Chichibabin) derivatives, formed by condensation of 2-aminopyridines with substituted dialkylmalonates, are electroactive. In solution in CH2Cl2/CF3CO2H mixtures they are smoothly and selectively anodically coupled in high yield. The products are novel and unexpected; radical coupling at the C-3 and O-4 positions is involved and the proposed mechanism is analogous to that of oxidative phenolic coupling.

  DOI：

  10.1016/s0040-4020(01)87057-5

文献信息

• Efficient synthesis of novel pyrano[2,3- d ]pyrido[1,2- a ]pyrimidine derivatives via isocyanide-based three-component reactions
  作者：Abbas Ali Esmaeili、Fariba Salehan、Azizollah Habibi、Ali Reza Fakhari

  DOI：10.1016/j.tetlet.2015.11.073

  日期：2016.1

  The synthesis of novel tricyclic fused pyrano[2,3-d]pyrido[1,2-a]pyrimidines containing both biologically active pyridopyrimidine and pyranopyrimidine scaffolds, via the reaction of 2H-pyrido[1,2-a]pyrimidine-2,4(3H)-dione, isocyanides, and dialkylacetylenedicarboxylates are reported. The products were obtained in good to excellent yields over short reaction times and with a simple work-up procedure

  通过2 H-吡啶并[1,2 - a ]嘧啶-2的反应合成新型的三环稠合吡喃并[2,3- d ]吡啶并[1,2- a ]嘧啶，它们同时具有生物活性吡啶并嘧啶和吡喃并嘧啶骨架报道了，4（3 H）-二酮，异氰化物和二烷基乙炔二羧酸酯。在较短的反应时间内，通过简单的后处理程序就可以以良好的收率获得优异的产物。
• Electro-organic reactions part 35. Efficient carbon—oxygen bond formation in the anodic coupling of pyridopyrimidine derivatives.
  作者：Mustafa Gullu、Liaquat A. Razack、James H.P. Utley、Ronald J. King、G.Ray White

  DOI：10.1016/s0040-4020(01)87057-5

  日期：1991.1

  4-H-Pyrido[1,2-a]pyrimidine-2,4-diones (Chichibabin) derivatives, formed by condensation of 2-aminopyridines with substituted dialkylmalonates, are electroactive. In solution in CH2Cl2/CF3CO2H mixtures they are smoothly and selectively anodically coupled in high yield. The products are novel and unexpected; radical coupling at the C-3 and O-4 positions is involved and the proposed mechanism is analogous to that of oxidative phenolic coupling.
• Synthesis, characterization, and urease inhibition of 5-substituted-8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-diones
  作者：Abdul Rauf、Sumaira Liaqat、Ashfaq M. Qureshi、Muhammad Yaqub、Aziz U. Rehman、Mahmood U. Hassan、Zahid H. Chohan、Faiz U. H. Nasim、T. Ben Hadda

  DOI：10.1007/s00044-010-9491-2

  日期：2012.1

  5-Substituted-8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-dione and its anilines, amino pyridines and hydrazides derivatives were prepared in a good to excellent yields. In the first step 8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-dione (1) was prepared by reacting 4-methyl-2-aminopyridine, with diethylmalonate. Compounds substituted pyrido[1,2-a]pyrimidine-2,4(3H)-diones (PPMDO) (2)-(17) were prepared by condensing 8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-dione in the presence of triethylorthoformte (TEF) and dimethylformamide (DMF), with respective amino components viz. 2-aminoacetophenone, 3-aminoacetophenone, 4-aminoacetophenone, 2,4,6-trimethylaniline, 2-fluoroaniline, 3-fluoroaniline, 4-fluoroaniline, 2-aminothiophenol, 2-amino-4-methylpyridine, 2-amino-5-methylpyridine, 2-amino-5-nitropyridine, Benzoic hydrazide, 4-nitrobenzoic hydrazide, 4-bromobenzoic hydrazide, 4-chlorobenzoic hydrazide and 4-hydroxybenzoic hydrazide, respectively. The chemical structures of all the compounds were elucidated by IR, H-1-NMR, C-13-NMR and elemental analysis data. The synthesized compounds were screened for their in vitro urease inhibition activity, by the phenol hypochlorite method. These compounds were found to exhibit either no or low to moderate or significant activity. The compounds (9) and (14) showed comparatively much higher activity. However, the compound (9) was found to be the most active one.