ethyl 3-amino-1-(4-methoxyphenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1, 2-b] phthalazine-2-carboxylate | 1338802-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: ethyl 3-amino-1-(4-methoxyphenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1, 2-b] phthalazine-2-carboxylate
• 英文别名: ethyl 3-amino-5,10-dihydro-1-(4-methoxyphenyl)-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carboxylate；ethyl 3-amino-5,10-dihydro-5,10-dioxo-1-p-methoxy-1H-pyrazolo[1,2-b]phthalazine-2-carboxylate；ethyl 3-amino-1-(4-methoxyphenyl)-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carboxylate
• CAS: 1338802-46-2
• 化学式: C₂₁H₁₉N₃O₅
• 分子量: 393.399
• InChiKey: JWIALUAFFQSHKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  邻苯二甲酰肼 、 4-甲氧基苯甲醛 、 氰乙酸乙酯 反应 0.08h， 以91%的产率得到ethyl 3-amino-1-(4-methoxyphenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1, 2-b] phthalazine-2-carboxylate
  参考文献：
  名称：

  1 H-吡唑并[1,2 - b ]酞嗪-5,10-二酮衍生物的高效绿色合成及其光物理研究

  摘要：

  特定任务的离子型液体，[BMIM] OH，已被用于为1的有效合成ħ -吡唑并[1,2- b ]酞嗪-5,10-二酮通过邻苯二甲酰的一锅反应环化缩合，芳族醛，微波辐射下的丙二腈或氰基乙酸乙酯。该方法的优点包括使用绿色催化剂，不使用有机溶剂，易于后处理和优异的收率。首次研究了一些1 H-吡唑并[1,2 - b ]酞嗪-5,10-二酮衍生物的光物理性质。

  DOI：

  10.1016/j.tetlet.2011.08.111

文献信息

• A Rapid and an Efficient Route to the One-pot, Multicomponent Synthesis of 1<i>H</i>-Pyrazolo[1,2-<i>b</i>]phthalazine-5,10-dione Ring Systems
  作者：Mazaahir Kidwai、Ritika Chauhan

  DOI：10.1002/jhet.1809

  日期：2014.11

  CAN is found to be an efficient catalyst for the synthesis of 1H‐pyrazolo[1,2‐b]phthalazine‐5,10‐dione derivatives via one‐pot coupling reaction of phthalhydrazide, aromatic aldehydes, and malononitrile or ethyl cyanoacetate in PEG as solvent. The major attributes of this synthetic protocol are the use of nontoxic, inexpensive, and readily available catalyst, mild conditions, easy work up, improved

  CAN是通过邻苯二甲酰肼，芳族醛，丙二腈或氰基乙酸乙酯在PEG中的一锅偶联反应合成1 H-吡唑并[1,2 - b ]酞嗪-5,10-二酮衍生物的有效催化剂作为溶剂。该合成方案的主要属性是使用无毒，廉价且易于获得的催化剂，温和的条件，易于后处理，提高的收率，以及PEG 400作为对环境无害且可回收的溶剂。
• Efficient and convenient synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives mediated by L-proline
  作者：Harendra Nath Roy、Masud Rana、Abu Zafar Al Munsur、Kee-In Lee、Ashis K. Sarker

  DOI：10.1080/00397911.2016.1192650

  日期：2016.8.17

  ABSTRACT An efficient, four-component, one-pot condensation reaction of phthalimide or phthalic anhydride, aromatic aldehydes, and ethyl cyanoacetate for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives mediated by L-proline in excellent yields is reported. GRAPHICAL ABSTRACT

  摘要 邻苯二甲酰亚胺或邻苯二甲酸酐、芳香醛和氰乙酸乙酯的高效、四组分、一锅缩合反应，用于合成由 L 介导的 1H-吡唑并[1,2-b]酞嗪-5,10-二酮衍生物-脯氨酸的产率很高。图形概要
• Synthesis of a diversified combinatorial library of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives applying sustainable carbon-based solid acid catalyst involving a domino four-component reaction
  作者：Koyel Pradhan、Sanjay Paul、Asish R. Das

  DOI：10.1007/s00706-014-1195-8

  日期：2014.8

  of the catalyst were determined by a nitrogen adsorption–desorption isotherm experiment. A highly efficient multicomponent heteroannulation protocol for the synthesis of a library of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives has been developed by applying the solid acid catalyst. This synthesis was established to follow the group-assistant-purification chemistry process avoiding traditional

  摘要通过磺化，水热碳化法，由可再生资源聚乙二醇合成了一种含SO 3 H的碳质固体催化剂。通过XRD，TEM，FT-IR和能量色散X射线对可生物降解的催化剂进行了表征。催化剂的表面积和孔径通过氮吸附-解吸等温线实验确定。用于合成1 H-吡唑并[1,2- b通过应用固体酸催化剂已经开发了[] 5，10-二酮酞嗪衍生物。建立该合成方法遵循的是避免传统色谱分离的组辅助纯化化学过程。水性反应介质，催化剂的易于回收以及产物的高收率使得该方案具有吸引力，可持续性和经济性。这项工作不仅可能导致环境友好的系统，而且还将提供水中有机化学的新方面。 图形概要
• SiO2:MgMnO3: An Efficient Heterogeneous Catalyst for One Pot Synthesis of 1H-Pyrazolo[1,2-b]phthalazine-5,10-dione Derivatives
  作者：S.S. Sagar、R.P. Chavan

  DOI：10.14233/ajchem.2020.22707

  日期：——

  indicates a good catalytic property. The synthesized catalyst was applied for the synthesis of 1H-pyrazolo[1,2-b]-phthalazine-5,10-dione in presence of ethanol as a solvent at 80 ºC. The current procedure and catalyst offers the gains of clean reaction, short reaction time, high yield, easy purification and financial availability of the catalyst.

  本研究涉及SiO2复合MgMnO3催化剂的水热合成。使用物理研究技术（包括 XRD、SEM、EDAX、TEM、SAED 和 BET 表面积）对获得的多晶产物进行分析。根据TEM图像，产物对应于100nm的平均粒径。SiO2复合MgMnO3催化剂的BET比表面积为234.38 cm2/g，表明其具有良好的催化性能。合成的催化剂用于在乙醇为溶剂、80 ℃下合成1H-吡唑并[1,2-b]-二氮杂萘-5,10-二酮。目前的方法和催化剂提供了反应清洁、反应时间短、产率高、易于纯化和催化剂的经济可用性的优点。
• Post synthesis alumination of KIT-6 materials with Ia3d symmetry and their catalytic efficiency towards multicomponent synthesis of 1H-pyrazolo[1,2-]phthalazine-5,10-dione carbonitriles and carboxylates
  作者：G. Karthikeyan、A. Pandurangan

  DOI：10.1016/j.molcata.2012.05.003

  日期：2012.9

  Alumination of Si-KIT-6 materials with ordered three-dimensional (3D) structure were prepared by post-synthesis method with various Si/Al ratios. The catalysts were characterized by X-ray diffraction analysis (XRD), N-2 porosimetry and FT-IR spectra. The presence of framework and extra framework aluminium was predicted by Aluminium MAS NMR. The strength of the acid sites of the catalysts was studied by NH3-TPD acidity measurements. The morphology of mesoporous materials was studied by SEM and TEM observation. The metal content of the samples was investigated by ICP-OES. The prepared solid acid catalysts were applied for the multi-component synthesis of 1H-pyrazolo[1,2-]phthalazine-5,10-diones from the reaction of phthalhydrazide, malononitrile/ethylcyano acetate and aromatic aldehyde in ethanol under liquid phase conditions. Activities of the catalysts follow the order: Al-KIT-6 (33) > Al-KIT-6 (56) > Al-KIT-6 (81) > Al-KIT-6 (110) > Nafion-H > Amberlyst-15 >> HM (12) > H beta (8) > HY (4). The effects of reaction conditions and different catalysts have been studied. Various advantages associated with these protocols include effective catalysis, simple work-up procedure, short reaction times, high product yields, easy recovery and reusability of the catalysts. (c) 2012 Elsevier B.V. All rights reserved.