6-amino-3-methyl-4-(1H-pyrrol-2-yl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 6-amino-3-methyl-4-(1H-pyrrol-2-yl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• 英文别名: 6-amino-3-methyl-4-(1λ²-pyrrol-2-yl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile；6-amino-3-methyl-4-(1H-pyrrol-2-yl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• 化学式: C₁₂H₁₁N₅O
• 分子量: 241.252
• InChiKey: RTECONIOSDMTJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-吡咯甲醛 、 3-甲基-2-吡唑啉-5-酮 、 丙二腈 在 一水合肼 、 三乙胺 作用下， 以 neat (no solvent) 为溶剂， 反应 0.27h， 以89%的产率得到6-amino-3-methyl-4-(1H-pyrrol-2-yl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
  参考文献：
  名称：

  Novel Grinding Synthesis of Pyranopyrazole Analogues and Their Evaluation as Antimicrobial Agents

  摘要：

  The paper describes the results of a new four-component synthesis of pyranopyrazole heterocycles by solvent-free one-pot grinding of malononitrile, hydrazine, ethyl acetoacetate, and various aldehydes in the presence of a base. The reaction proceeded smoothly at room temperature with good yields in very short reaction time. The synthesised compounds were evaluated for their in vitro antibacterial activity against three different bacterial and three different fungal strains. The highlight of this work is that the synthesis was activity-driven. The brief SAR correlation found that the tested compounds showed better activity against fungal strains.

  DOI：

  10.3987/com-15-13222

文献信息

• An Organobase (TBD)-Anchored Mesoporous Silica Nanoparticle-Catalyzed Green Synthesis of Dihydropyrano[2,3-c]pyrazoles
  作者：Bikash Karmakar

  DOI：10.1071/ch15812

  日期：——

  An efficient, mild, and environmental friendly method has been developed for the synthesis of dihydropyrano[2,3-c]pyrazole in ethanolic water over 1,5,7-triazabicyclo-[4,4,0]-dec-1-ene (TBD)-anchored mesoporous silica nanoparticle catalyst. The method involves the assembly of ethyl acetoacetate, hydrazine hydrate, different aldehydes, and malononitrile. It affords the corresponding product in high yield with short reaction times, while employing a very low loading of catalyst. The catalyst was reused several times without significant loss in activity.

  在 1,5,7- 三氮杂双环-[4,4,0]-癸-1-烯（TBD）锚定介孔二氧化硅纳米粒子催化剂上，开发了一种在乙醇水中合成二氢吡喃并[2,3-c]吡唑的高效、温和且环保的方法。该方法涉及乙酰乙酸乙酯、水合肼、不同的醛和丙二腈的组装。该方法能以较短的反应时间获得高产率的相应产品，同时催化剂的负载量极低。催化剂可重复使用多次，而活性不会明显降低。
• Green Synthesis of Pyrano[2,3-<i>c</i>]pyrazoles and Spiro[indoline-3,4′-pyrano[2,3-<i>c</i>]pyrazoles] Using Nano-silica Supported 1,4-Diazabicyclo[2.2.2]octane as a Novel Catalyst
  作者：Naeimeh Salehi、Bi Bi Fatemeh Mirjalili

  DOI：10.1080/00304948.2018.1537748

  日期：2018.11.2

  step-economy (PASE). Combining synthetic potentialities of MCRs and principles of green chemistry can provide efficient ways to develop new eco-compatible methodologies. Pyrano[2,3-c]pyrazoles have attracted considerable interest in organic synthesis because of their wide application in medicinal and pharmaceutical chemistry. Many of these moieties are known for their antimicrobial, anti-inflammatory, anticancer

  多组分反应 (MCR) 由于其锅、原子和步进经济 (PASE) 而在开发分子设计和组合化学方面发挥着重要作用。将 MCR 的合成潜力与绿色化学原理相结合，可以提供有效的方法来开发新的生态兼容方法。吡喃并[2,3-c]吡唑因其在药物和药物化学中的广泛应用而在有机合成中引起了相当大的兴趣。许多这些部分以其抗微生物、抗炎、抗癌、杀软体动物和激酶抑制活性而闻名。此外，螺环吲哚是在药物和天然产品中发现的独特核心结构，如螺环前列腺素 (A & B)、Pteropodine、Marcfortine B 和 Glesemine。此外，据报道，2-氧代吲哚的 3 位螺碳原子显着增强了生物活性。考虑到这些结构基序的生物学意义，已经进行了许多努力来开发它们的合成方法，从多步反应到一锅四组分反应。所有报告的方法都有其自身的优点和一些缺点。1,4-二氮杂双环[2.2.2]辛烷（DABCO）作为一种方便、廉价且环境友
• Bread waste in the form of CoFe2O4@TBW catalyst was used as a green biocatalyst to synthesize pyranopyrazole and tetraketone derivatives
  作者：Firouz Matloubi Moghaddam、Sara Aghili、Maryam Daneshfar、Hamid Moghimi、Zahra Daneshfar

  DOI：10.1007/s11164-022-04934-z

  日期：2023.4

  spinels were utilized to synthesize core–shell magnetic nanocatalyst. The prepared heterogeneous catalyst was characterized using Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), scanning electron microscopy (SEM), Brunauer–Emmett–Teller (BET), thermogravimetric analysis (TGA), and transmission electron microscopy (TEM). This magnetic nanocatalyst opens up a new avenue to introduce

  含有过渡金属氧化物尖晶石的面包屑被用来合成核-壳磁性纳米催化剂。使用傅里叶变换红外光谱 (FTIR)、X 射线衍射 (XRD)、扫描电子显微镜 (SEM)、Brunauer–Emmett–Teller (BET)、热重分析 (TGA) 和透射电子显微镜 (透射电镜）。这种磁性纳米催化剂开辟了一条新途径，通过 1,3 环己二酮和苯甲醛在乙醇中作为绿色溶剂在 50 °C 下通过 Knoevenagel-Micheal 反应一锅法合成四酮衍生物，从而引入一种非常有用和高效的催化系统，以及苯甲醛、双甲酮、乙酰乙酸乙酯和水合肼通过串联 Knoevenagel-Micheal 反应一锅法四组分反应合成二氢吡喃[2, 3-c] 乙醇中的吡唑衍生物。二氢吡喃并 [2,3-c] 吡唑和四酮的药学特性使它们成为必需的化合物。此外，新型多相磁性催化剂的可回收性不会显着降低其催化活性，并且可以通过外部磁铁轻松回收并重复使用
• Aqueous TPGS-750-M-mediated synthesis of pyrano[2,3-c]-pyrazoles: a sustainable and efficient approach
  作者：Adnan Cetin、Mehmet Yasin Bayden

  DOI：10.1007/s11164-024-05280-y

  日期：——

  describes a green and efficient synthesis method for pyrano[2,3-c]-pyrazoles, employing DL-alpha-tocopherol methoxypolyethylene glycol succinate solution (TPGS-750-M) as a green and biodegradable surfactant in water. The utilization of water as a reaction medium and TPGS-750-M as a surfactant obviates the necessity for organic solvents, thereby enhancing the environmental sustainability of the synthesis. The

  该文章描述了一种吡喃并[2,3-c]-吡唑类化合物的绿色高效合成方法，采用DL-α-生育酚甲氧基聚乙二醇琥珀酸酯溶液（TPGS-750-M）作为绿色、可生物降解的表面活性剂在水中。利用水作为反应介质和TPGS-750-M作为表面活性剂消除了对有机溶剂的需求，从而提高了合成的环境可持续性。使用各种光谱技术（包括1 H-NMR、13 C-NMR 和质谱）对使用这种新方法合成的化合物进行了表征。 图形概要
• One-Pot Synthesis of 6-Amino-4-(furan/thiophen/pyrrol-2-yl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles, Evaluation of Anticancer Activity and Molecular Modelling Studies
  作者：K. Kalpana、V. A. Rani、A. Ranga、R. Perumandla、R. Ramani

  DOI：10.1134/s1070363223010188

  日期：2023.1