7-amino-5-(3,4-dimethoxyphenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃嘧啶类
• 英文名称: 7-amino-5-(3,4-dimethoxyphenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile
• 英文别名: 7-amino-5-(3,4-dimethoxyphenyl)-2,4-dioxo-1,3,4,5-tetrahydro-2H-pyrano[2,3-d]pyrimidine-6-carbonitrile；7-amino-5-(3,4-dimethoxyphenyl)-2,4-dihydroxy-5H-pyrano[2,3-d]pyrimidine-6-carbonitrile；7-amino-5-(3,4-dimethoxyphenyl)-2,4-dioxo-1,5-dihydropyrano[2,3-d]pyrimidine-6-carbonitrile
• 化学式: C₁₆H₁₄N₄O₅
• 分子量: 342.311
• InChiKey: QGXNUGHUBLXPPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  巴比妥酸 、 ((3,4-二甲氧基苯基)亚甲基)甲烷-1,1-二甲腈 在 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 反应 5.0h， 以95%的产率得到7-amino-5-(3,4-dimethoxyphenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile
  参考文献：
  名称：

  Green Synthesis of Pyrano[2,3‐d]‐pyrimidine Derivatives in Ionic Liquids

  摘要：

  Pyrano[2,3-d]pyrimidine derivatives were synthesized in high yields by a condensation reaction between arylmethylidenemalononitrile and barbituric acid using room-temperature ionic liquids such as 1- n -butyl-3-methylimidazolium tetrafluoroborate ([BMIm]BF4) or 1-butylpyridinium tetrafluoroborate ([BPy]BF4) as solvents under neutral conditions.

  DOI：

  10.1080/00397910500282661

文献信息

• Synthesis of functionalized chromene and spirochromenes using l -proline-melamine as highly efficient and recyclable homogeneous catalyst at room temperature
  作者：Sakkani Nagaraju、Banoth Paplal、Kota Sathish、Santanab Giri、Dhurke Kashinath

  DOI：10.1016/j.tetlet.2017.09.060

  日期：2017.11

  commercially cheap l-proline and melamine for the synthesis of chromenes and spirochromenes (spirooxindoles) via multicomponent reactions at room temperature. Systematic studies were conducted in order to achieve desired reactivity and recyclability of the catalyst using various α-amino acids and aromatic amines as donor-acceptor pairs. Among the screened combinations, l-proline and melamine (3:1 ratio;

  使用便宜的1-脯氨酸和三聚氰胺开发了一种有效且可循环使用的均相催化剂，用于在室温下通过多组分反应合成色烯和螺环色酮（螺并辛多烯）。为了使用各种α-氨基酸和芳族胺作为供体-受体对，进行系统研究以实现所需的反应性和催化剂的可回收性。在筛选的组合中，l脯氨酸和三聚氰胺（3：1的比例；占总重量的3 mol％）被认为是最佳的催化剂，可以在室温下非常短的时间内（1-15分钟）以优异的产率（高达99％）提供所需的产品在DMSO中作为溶剂。通过添加EtOAc来回收催化剂，并且在不损失催化活性的情况下重复使用多达5个循环。
• Effect of Liquid Glass Composition on the Catalytic Preparation of Pyrano[2,3-d]pyrimidine Derivatives
  作者：Mehdi Abaszadeh、Seyyed Jalal Roudbaraki、Majid Ghashang

  DOI：10.1080/00304948.2019.1600124

  日期：2019.5.4

  compounds containing at least one core moiety of pyrano[2,3-d]pyrimidine have received considerable attention in synthetic organic chemistry because of their potential as drugs and bioactive compounds. Pyrano[2,3-d]pyrimidines have attracted interest in medicine as antitumor, anti-hypertensive, antibacterial and antileishmanial drugs. Pyrano[2,3-d]pyrimidines have been produced by a number of methods. A

  本研究的主要目的是使用液态玻璃作为催化剂催化制备5-芳基-1,3,4,5-四氢2H-吡喃并[2,3-d]嘧啶-6-腈衍生物。所有反应均在水中回流条件下进行。作为进一步的目标，使用高速球磨 (HSBM) 技术研究了该过程。研究了液态玻璃成分和添加金属氧化物杂质的影响。最近，含有至少一个吡喃并[2,3-d]嘧啶核心部分的化合物因其作为药物和生物活性化合物的潜力而在合成有机化学中受到了相当大的关注。吡喃并[2,3-d]嘧啶作为抗肿瘤、抗高血压、抗菌和抗利什曼病药物在医学上引起了人们的兴趣。吡喃并[2,3-d]嘧啶已通过多种方法生产。可以获得对合成程序的完整审查和关于这些化合物的讨论。分子式为 Na2(SiO2)nO 的液态玻璃是一种硅酸钠水溶液，可通过 NaOH (25%) 与 SiO2 反应或通过将碳酸钠与二氧化硅熔化来制备。数十年来，液态玻璃一直被用作粘合剂和涂层剂。液态玻璃是一种无毒、耐热
• Synthesis, biological activity and POM/DFT/docking analyses of annulated pyrano[2,3-d]pyrimidine derivatives: Identification of antibacterial and antitumor pharmacophore sites
  作者：Ajmal R. Bhat、Rajendra S. Dongre、Faisal A. Almalki、Malika Berredjem、Mohamed Aissaoui、Rachid Touzani、Taibi Ben Hadda、Mohammad S. Akhter

  DOI：10.1016/j.bioorg.2020.104480

  日期：2021.1

  on its antimicrobial activity against some Gram-positive and Gram-negative bacteria such as Pseudomonas aureus, E. coli, Staphylococcus aureus, Klebsiella pneumonia and Bacillus cereus. All the pyrano[2,3-d]pyrimidines were characterized by spectroscopic analyses. Antibacterial screening revealed that the presence of heteroaryl, cyano and amino groups on pyrano[2,3-d]pyrimidine skeleton increases its

  合成了新的环状吡喃并[2,3-d]嘧啶衍生物，其骨架上带有羟基、甲氧基、溴、腈和硝基取代基。注意到取代基对抗菌活性大小的相关电子效应。吡喃并[2,3-d]嘧啶骨架中苯环上的给电子取代基（即：4-OH、4-OCH 3、4-Br）和吸电子取代基（4-NO 2）对其产生不同的影响。对一些革兰氏阳性和革兰氏阴性细菌如金黄色葡萄球菌、大肠杆菌、金黄色葡萄球菌、肺炎克雷伯菌和蜡状芽孢杆菌的抗菌活性。所有吡喃并[2,3-d]嘧啶均通过光谱分析表征。抗菌筛选表明，吡喃并[2,3-d]嘧啶骨架上杂芳基、氰基和氨基的存在增加了其对细菌细胞壁的渗透能力，从而使产物变得更具生物活性。因此在药物设计中应考虑吸电子或供电子体的性质对取代基的影响。 -CRN 水解为酰胺恢复了重要的分子内相互作用，如邻硝基苯基和 -ONO δ- ...-NH δ+/酰胺链接，为抗菌-NH、H2O-药团位点提供了关键模板，最终提高了先天抗菌谱。由于武装环状吡喃并
• Fabrication and characterization of adenine‐grafted carbon‐modified amorphous ZnO with enhanced catalytic activity
  作者：Bushra Chowhan、Monika Gupta、Neha Sharma

  DOI：10.1002/aoc.6013

  日期：2020.12

  carbon‐modified amorphous ZnO nanocatalyst (ZnO@AC) derived from garment industry waste (waste cotton cloth). Due to adenine functionality, catalyst provides consistent dispersion of ZnO providing catalytically active sites for the synthesis of pyrano[2,3‐d]pyrimidines and bis(pyrazol‐5‐ole) and alters the electron–hole pair recombination without notable mass‐transfer limitation. The photocatalytic evaluation

  可持续性已经成为当前纳米催化领域的标志和指导原则。在此，我们报道了一种成本效益高，绿色环保，清洁高效的工艺，该工艺可用于制衣业废料（废棉布）形成的腺嘌呤接枝的碳改性无定形ZnO纳米催化剂（ZnO @ AC）。由于腺嘌呤官能团，催化剂可提供一致的ZnO分散，从而为吡喃并[2,3- d]嘧啶和双（吡唑-5-烯烃）并改变电子-空穴对的重组，而没有明显的传质限制。ZnO @ AC的光催化评价是在紫外光下对甲基橙（MO）染料进行的，在75分钟内降解率为87.3％。此外，该催化剂可回收利用，最多可重复使用八次，使其更具可持续性。根据所用催化剂的透射电子显微镜（TEM）图像，经过八次回收后，ZnO @ AC的形态仍保持完整，ZnO纳米颗粒（nps）发生了轻微的团聚。
• Bentonite-titana Composite as an Efficient, Eco-friendly and Non-toxic Catalyst for Synthesis of Benzopyran Derivatives Under Heating and Solvent-free Conditions
  作者：Ali Darehkordi、Mohammad Hosseini、Mirrasol Mosavi、Alireza Poorfreidoni

  DOI：10.2174/1570178612666150108002202

  日期：2015.3.3

  Bentonite-titana composite was prepared and characterized by XRD, FT-IR and SEM. Results indicate that TiO2 particles have been supported on the bentonite layers and a delaminated structure is formed. Then the bentonitetitana composite as a mild, eco-friendly, non-toxic an efficient heterogeneous catalyst have been used for synthesis of benzopyran derivatives from the three-component condensation reaction of dimedone or barbituric acid, malonoitrile, and aromatic aldehydes under solvent free conditions in good to excellent yield and short reaction times.

  膨润土-钛酸盐复合材料通过XRD、FT-IR和SEM进行了制备和表征。结果表明，TiO2颗粒被支持在膨润土层上，形成了分层结构。随后，该膨润土-钛酸盐复合材料作为一种温和、环保、无毒且高效的异相催化剂，用于在无溶剂条件下，通过二羟基乙酰酮或巴比妥酸、琥珀腈和芳香醛的三组分缩合反应合成苯并吡喃衍生物，反应产率良好到优秀且反应时间短。