5-(3-p-tolyl-1,2,4-oxadiazol-5-yl)pyrimidine-2,4(1H,3H)-dione | 1350660-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(3-p-tolyl-1,2,4-oxadiazol-5-yl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 5-[3-(4-methylphenyl)-1,2,4-oxadiazol-5-yl]-1H-pyrimidine-2,4-dione
• CAS: 1350660-71-7
• 化学式: C₁₃H₁₀N₄O₃
• 分子量: 270.247
• InChiKey: GURQFSAKDABMTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  97.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  p-methylbenzaldehyde oxime 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 5-(3-p-tolyl-1,2,4-oxadiazol-5-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of 5-hetaryluracil derivatives via 1,3-dipolar cycloaddition reaction

  摘要：

  1,3-Dipolar cycloaddition is a convenient method for construction of various heterocyclic systems. We applied this method for the synthesis 5-hetaryluracil derivatives where substituted uracils played the role of 1,3-dipoles or dipolarophiles. Treatment of the nitrile oxide derived from 5-formyluracil and substituted alkenes gave the appropriate 5-(4,5-dihydroisoxazol-3-yl)pyrimidine-2,4(1H, 3H)-diones, which by oxidation with N-bromosuccinimide were transformed into appropriate 5-(isoxazol-3-yl)uracils. When 5-cyanouracil was used as a dipolarophile in the reaction with nitrile oxides, generated from aromatic aldoximes, several 5-(1,2,4-oxadiazol-5-yl) uracils were obtained. An alternative reaction of 5-formyluracil with an excess of nitriles in the presence of cerium ammonium nitrate as an oxidant gave 1,2,4-oxadiazol-3-yl derivatives in moderate yields.

  DOI：

  10.3998/ark.5550190.p009.754

文献信息

• A convenient synthesis of 5-(1,2,4-oxadiazol-5-yl)pyrimidine-2,4(1H,3H)-diones
  作者：Dominika Jakubiec、Krzysztof Z. Walczak

  DOI：10.1016/j.tetlet.2011.10.033

  日期：2011.12

  The synthesis of 5-heteroaryl-substituted uracil derivatives is presented. The 1,3-dipolar cycloaddition reaction was applied for the construction of a heterocyclic ring. The nitrile oxides were obtained from the appropriate 4-substituted benzaldoximes using N-chlorosuccinimide (NCS) under basic conditions. [2+3] Cycloaddition of nitrile oxides with 5-cyanouracil as a dipolarophile gave the corresponding

  介绍了5-杂芳基取代的尿嘧啶衍生物的合成。将1，3-偶极环加成反应用于杂环的构建。在碱性条件下，使用N-氯琥珀酰亚胺（NCS）从适当的4-取代的苯甲醛肟中获得腈氧化物。[2 + 3]用5-氰尿嘧啶作为双极性亲和剂与腈类化合物环加成，在温和条件下以令人满意的收率得到相应的5-（3-取代-1,2,4-恶二唑-5-基）尿嘧啶。通过将5-氰尿嘧啶[2 + 3]环加成到由噻吩-2-甲醛和5-甲酰尿嘧啶衍生物生成的腈氧化物中，获得了具有额外杂环的5-取代尿嘧啶。