7-amino-5-(4-cyanophenyl)-2,4-dioxo-1,3,4,5-tetrahydro-2H-pyrano[2,3-d]pyrimidine-6-carbonitrile | 365517-01-7

• 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-(4-cyanophenyl)-2,4-dioxo-1,3,4,5-tetrahydro-2H-pyrano[2,3-d]pyrimidine-6-carbonitrile
• 英文别名: 7-Amino-5-(4-cyanophenyl)-2,4-dioxo-1,5-dihydropyrano[2,3-d]pyrimidine-6-carbonitrile
• CAS: 365517-01-7
• 化学式: C₁₅H₉N₅O₃
• 分子量: 307.268
• InChiKey: QCHXXEROQOTZNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  141
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  potassiumhexacyanoferrate(II) trihydrate 、 7-amino-5-(4-bromophenyl)-2,4-dioxo-1,3,4,5-tetrahydro-2H-pyrano[2,3-d]pyrimidine-6-carbonitrile 在 sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以58%的产率得到7-amino-5-(4-cyanophenyl)-2,4-dioxo-1,3,4,5-tetrahydro-2H-pyrano[2,3-d]pyrimidine-6-carbonitrile
  参考文献：
  名称：

  Immobilized palladium nanoparticles on a cyclodextrin-polyurethane nanosponge (Pd-CD-PU-NS): An efficient catalyst for cyanation reaction in aqueous media

  摘要：

  Immobilized palladium nanoparticles on a cyclodextrin-polyurethane nanosponge (Pd-CD-PU-NS) were found to be an efficient heterogeneous catalyst in the cyanation reaction of aryl halides in aqueous media. This catalyst system is containing palladium nanoparticles with a size of similar to 7 nm. Moreover, the CD-PU-NS support formed microsphere-shaped structures with a size of similar to 100-200 nm. The TEM images show that Pd nanoparticles were formed in near spherical shape morphology and were immobilized in the structure of the CD-PU-NS support. Under our optimized reaction conditions, aryl cyanides were obtained in high yields in the presence of the Pd-CD-PU-NS catalyst. Our results demonstrated that the Pd-CD-PU-NS catalyst is highly effective in the cyanation reaction in aqueous media. Furthermore, the catalyst could be simply extracted from the reaction mixture, providing an efficient methodology for the synthesis of aryl cyanides. The Pd-CD-PU-NS catalyst could be recycled four times with almost consistent catalytic efficiency.

  DOI：

  10.1016/j.ica.2019.05.021

文献信息

• DABCO-based ionic liquids: green and recyclable catalysts for the synthesis of barbituric and thiobarbituric acid derivatives in aqueous media
  作者：Narges Seyyedi、Farhad Shirini、Mohaddeseh Safarpoor Nikoo Langarudi

  DOI：10.1039/c6ra05878g

  日期：——

  the reaction of barbituric or thiobarbituric acid, malononitrile and aldehydes in the presence of this reagent and 1,4-disulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium chloride ([DABCO](SO3H)2(Cl)2) has been investigated. The structure of the products was characterized using IR, 1H NMR and 13C NMR spectroscopy. The present methodologies suggests several advantages such as ease of the preparation and

  一种新的，直接的方法，可通过使用1,4-二磺基-1,4-二氮杂双环[2.2.2]辛烷-1通过巴比妥酸及其硫代类似物与醛的反应来合成5-芳基巴比妥酸和硫代巴比妥酸，已经报道了作为有效催化剂的4-二硫酸氢二钠（[DABCO]（SO 3 H）2（HSO 4）2）。在该项目中，还通过在该试剂和1,4-二磺基-1,4-二氮杂双环[2.2]存在下，通过巴比妥酸或硫代巴比妥酸，丙二腈和醛的反应制备吡喃并[2,3- d ]-嘧啶二酮。 .2]辛烷-1,4-氯化铵（[DABCO]（SO 3 H）2（Cl）2）已被调查。使用IR，1 H NMR和13 C NMR光谱对产物的结构进行表征。本方法论提出了若干优点，例如易于制备和处理催化剂，高收率，简单和绿色的方法，低成本，短的反应时间，易于后处理和在水中作为绿色溶剂进行反应的预形成。
• 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
• SCMNPs@Urea/Py-CuCl₂: a recyclable catalyst for the synthesis of pyrano[2,3-<i>d</i>]pyrimidinone and pyrano[2,3-<i>d</i>] pyrimidine-2,4,7-trione derivatives
  作者：Jun Zhang、Hongqing Song、Ruirui Cui、Chaoyong Deng、Qahtan A. Yousif

  DOI：10.1080/00958972.2020.1737681

  日期：2020.2.16

  Abstract An efficient, simple, and mild strategy for the one-pot multicomponent synthesis of pyrano[2,3-d]pyrimidinone and pyrano[2,3-d]pyrimidine-2,4,7-trione derivatives is described using SCMNPs@Urea/Py-CuCl2 nanoparticles as a reusable heterogeneous magnetic nanocatalyst. The catalyst was characterized using Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), vibrating

  摘要描述了使用 SCMNPs@ 一锅多组分合成吡喃并[2,3-d]嘧啶酮和吡并[2,3-d]嘧啶-2,4,7-三酮衍生物的高效、简单和温和的策略。尿素/Py-CuCl2 纳米颗粒作为可重复使用的异质磁性纳米催化剂。使用傅里叶变换红外光谱 (FTIR)、热重分析 (TGA)、振动样品磁强计 (VSM)、能量色散 X 射线光谱 (EDX)、X 射线衍射 (XRD) 和扫描电子显微镜 (SEM) 对催化剂进行表征。 ）。SCMNPs@Urea/Py-CuCl2 可以很容易地通过使用永磁场的磁滗析从反应溶液中收集，并在六次运行中重复使用，催化活性不会显着降低。图形概要
• Three-component synthesis of pyrano[2,3-d]pyrimidinone derivatives catalyzed by Ni2+ supported on hydroxyapatite-core–shell-γ-Fe2O3 nanoparticles in aqueous medium
  作者：Sobhan Rezayati、Zahra Abbasi、Eshagh Rezaee Nezhad、Rahimeh Hajinasiri、Abdolhadi Farrokhnia

  DOI：10.1007/s11164-016-2555-2

  日期：2016.10

  via one-pot, three-component condensation reaction of aromatic aldehydes, malononitrile, and barbituric acid in aqueous ethanol catalyzed by Ni2+ supported on hydroxyapatite-core–shell-γ-Fe2O3 nanoparticles (γ-Fe2O3@HAp-Ni2+ NPs) as Lewis acid. The nontoxic nature and easy handling of the catalyst, environmentally friendly and facile work-up procedure, short reaction time, low catalyst loading, and

  通过羟基磷灰石-核-壳-γ-Fe负载的Ni 2+催化芳香族醛，丙二腈和巴比妥酸在乙醇水溶液中的一锅三组分缩合反应合成了吡喃并[2,3- d ]嘧啶衍生物。2个ø 3纳米颗粒（γ-的Fe 2 ö 3 @的HAp-Ni系2+ NPS）作为路易斯酸。该方法的优点是无毒且催化剂易于处理，环保且易于后处理，反应时间短，催化剂用量低以及能以良好至极好的收率生产产品的高效性。另外，γ-的Fe 2 ö 3 @ HAP-的Ni 2+ NP可以轻松回收并重复使用至少六次。
• 4-Dialkylaminopyridine modified magnetic nanoparticles: as an efficient nano-organocatalyst for one-pot synthesis of 2-amino-4H-chromene-3-carbonitrile derivatives in water
  作者：Soheila Khajeh Dangolani、Farhad Panahi、Maryam Nourisefat、Ali Khalafi-Nezhad

  DOI：10.1039/c6ra18078g

  日期：——

  silica-coated magnetic nanoparticles (Fe3O4@SiO2) were reacted with trimethoxy(vinyl)silane. The MNP–DMAP catalyst shows remarkable activity in the synthesis of 2-amino-4H-chromene-3-carbonitrile derivatives using a multicomponent reaction under mild conditions in water as a green solvent. The MNP–DMAP was reusable in this process for at least 10 times without any treatment in its catalytic activity.

  通过将4-二烷基氨基吡啶部分固定在Fe 3 O 4磁性纳米颗粒（MNP–DMAP）上，开发了一种新型的异质磁性纳米有机催化剂。它是通过MNP-环氧乙烷（MNPO）与N-甲基吡啶-4-胺的反应合成的。通过使用H 2 O 2氧化乙烯基官能化的MNP（VMNP）表面上的乙烯基来生产MNPO基板。为了合成VMNP，使二氧化硅涂覆的磁性纳米颗粒（Fe 3 O 4 @SiO 2）与三甲氧基（乙烯基）硅烷反应。MNP–DMAP催化剂在2-氨基-4 H的合成中显示出显着的活性-Crene-3-carbontritrile衍生物在温和条件下于水中作为绿色溶剂使用多组分反应。MNP–DMAP在此过程中至少可重复使用10次，而无需对其催化活性进行任何处理。