3,3-dimethyl-13-(thiophen-2-yl)-3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-trione | 1345599-35-0

• 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: 3,3-dimethyl-13-(thiophen-2-yl)-3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-trione
• 英文别名: 2,3,4,13-Tetrahydro-3,3-dimethyl-13-(thiophen-2-yl)-indazolo[2,1-b]phthalazine-1,6,11-trione；3,3-dimethyl-13-thiophen-2-yl-4,13-dihydro-2H-indazolo[1,2-b]phthalazine-1,6,11-trione
• CAS: 1345599-35-0
• 化学式: C₂₁H₁₈N₂O₃S
• 分子量: 378.452
• InChiKey: HZRQQQXPLHPLBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 苯酐 、 5,5-二甲基-1,3-环己二酮 在 一水合肼 作用下， 以 neat (no solvent) 为溶剂， 反应 10957.5h， 以93%的产率得到3,3-dimethyl-13-(thiophen-2-yl)-3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-trione
  参考文献：
  名称：

  Fe3O4@SiO2-imid-催化的2H-吲唑并[2,1-b]酞嗪-三酮和1H-吡唑并[1,2-b]酞嗪-二酮的无溶剂、声化学、一锅四组分合成PMAn磁性纳米粒子

  摘要：

  一种使用 Fe 3 O 4 @SiO 2 -imid-PMA合成 2 H -吲唑并[2,1- b ]酞嗪三酮和 1 H -吡唑并[1,2- b ]酞嗪二酮的实用绿色方法n描述了纳米粒子作为一种环保磁性催化剂，来自邻苯二甲酸酐、氢氧化肼、1,3-二酮和醛的四组分缩合、无溶剂反应，在室温下进行热或超声辐照。这种新方法具有显着的优点，例如操作简单、产率高、反应时间短以及没有任何繁琐的后处理或纯化。此外，催化剂的热稳定性、易于制备和分离使其成为一种良好的多相体系，是其他多相催化剂的有用替代品。此外，催化剂可以很容易地通过磁场回收并重复使用八个连续的反应循环而不会显着损失活性。

  DOI：

  10.1007/s11164-016-2462-6

文献信息

• Solvent-free sonochemical one-pot three-component synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11-triones and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones
  作者：Gaurav Shukla、Rajiv K. Verma、Girijesh K. Verma、Maya Shankar Singh

  DOI：10.1016/j.tetlet.2011.10.136

  日期：2011.12

  A rapid and efficient one-pot three-component protocol for the synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11-triones 4 and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones 6 has been developed by domino coupling of phthalhydrazide, 1,3-diketones, and aldehydes under solvent-free conditions at 80 °C as well as under solvent-free ultrasound irradiation at room temperature promoted by (S)-camphorsulfonic

  一种快速高效的一锅三组分规程，用于合成2 H-吲唑并[2,1- b ]邻苯并-1,6,11-三酮4和1 H-吡唑并[1,2- b ]邻苯并-通过在80°C下无溶剂条件下以及（S）促进的室温下在无溶剂超声辐照下，将邻苯二甲酰肼，1,3-二酮和醛进行多米诺偶联，开发了5,10-二酮6。樟脑磺酸。
• Lewis acid free synthesis of 3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-triones promoted by 1,1,1,3,3,3-hexafluoro-2-propanol
  作者：Behrooz Maleki、Samaneh Sedigh Ashrafi、Reza Tayebee

  DOI：10.1039/c4ra06768a

  日期：——

  A convenient, environmentally friendly and efficient procedure for the synthesis 3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-trione derivatives has been developed via multi-component and one-pot reactions of various aldehydes with cyclic 1,3-diketones and phthalhydrazide 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). In simple and mild reaction conditions, the use of HFIP is explored as an easy workup and a green catalyst for the one-pot three-component synthesis of 3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-triones. Thus, this practical method is developed as a notable medium for these derivatives via a multicomponent reaction.

  通过各种醛与环状 1,3-二酮和酞酰肼 1,1,1,3,3,3-六氟-2-丙醇（HFIP）的多组分和一锅反应，开发了一种方便、环保和高效的 3,4-二氢-1H-吲唑并[1,2-b]酞嗪-1,6,11(2H,13H)-三酮衍生物的合成方法。在简单温和的反应条件下，研究人员探索了如何利用 HFIP 作为一种易于操作的绿色催化剂，一锅三组分合成 3,4- 二氢-1H-吲唑并[1,2-b]酞嗪-1,6,11(2H,13H)-三酮。因此，这种实用的方法被开发为通过多组分反应合成这些衍生物的显著介质。
• β-Cyclodextrine-SO3H: the most efficient catalyst for one-pot synthesis of 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions
  作者：Amol B. Atar、Sang Dong Lee、Byung Gwon Cho、Dae Won Cho、Yeon Tae Jeong

  DOI：10.1007/s11164-015-2113-3

  日期：2016.3

  Abstract An environmentally benign and efficient method has been developed for the synthesis of a series of 2H-indazolo[2,1-b]phthalazine-triones derivatives with β-cyclodextrine-SO3H as a recyclable catalyst by simply combining of various aldehydes with cyclic 1,3-diketones and phthalhydrazide under solvent free condition. The advantageous features of this methodology are high atom-economy, operational

  摘要 通过简单地将各种醛与环状化合物结合，已开发出一种环境友好的高效方法，用于合成一系列以β-环糊精-SO 3 H为催化剂的2H-吲唑并[2,1-b]邻苯二甲腈-三酮衍生物。1,3-二酮和邻苯二甲酰肼在无溶剂条件下使用。这种方法的优点是原子经济性高，操作简单，反应时间短，收敛性好，自动化程度高。 图形概要 首次开发了一种绿色环保，高效且快速的方法，以β-环糊精-SO 3 H作为可循环利用的催化剂来合成2H-吲唑并[2,1-b]酞嗪-三酮衍生物。
• Preparation, characterization and catalytic activity of dendrimer-encapsulated phosphotungstic acid nanoparticles immobilized on nanosilica for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones under solvent-free or sonochemical conditions
  作者：Mohsen Esmaeilpour、Jaber Javidi、Farzaneh Dehghani

  DOI：10.1007/s13738-015-0782-x

  日期：2016.4

  In this paper, we adopt a facile method to prepare a type of porous silica nanoparticles (n-SiO2) from tetraethyl orthosilicate as the source of silica. Then, dendritic polymer supported on nanosilica with surface amino groups was fabricated. Finally, H3PW12O40 nanoparticles (PWAn) were synthesized by the treatment of H3PW12O40 powder with n-Octane as solvent by a solvothermal method and then immobilized onto the dendrimer polymer functionalized nanosilica. The synthesized nanostructures were characterized by fourier transform infrared (FT-IR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), dynamic light scattering (DLS), N2 adsorption–desorption isotherm analysis, UV–Vis and elemental analysis. The morphology of the catalyst was characterized using transmission electron microscopes (TEM). The acidity of the catalyst was determined by FTIR pyridine adsorption spectroscopy. Then, this catalytic system was used as an efficient catalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones via multi-component and one-pot reactions of various aldehydes, phthalic anhydride, hydrazinium hydroxide, and dimedone under thermal solvent-free conditions or ultrasound irradiation at room temperature. Also, the catalyst can be easily recovered and reused for six consecutive reaction cycles without significant loss of activity.

  本文采用一种简便的方法，以正硅酸四乙酯为硅源制备了一种多孔纳米二氧化硅（n-SiO2）。然后，在纳米二氧化硅上制备了带有表面氨基的树枝状聚合物。最后，以正辛烷为溶剂，通过溶热法处理 H3PW12O40 粉末，合成了 H3PW12O40 纳米粒子（PWAn），并将其固定在树枝状聚合物功能化的纳米二氧化硅上。傅立叶变换红外（FT-IR）、X 射线衍射（XRD）、热重分析（TGA）、动态光散射（DLS）、N2 吸附-解吸等温线分析、紫外-可见光和元素分析对合成的纳米结构进行了表征。使用透射电子显微镜（TEM）对催化剂的形态进行了表征。催化剂的酸度是通过傅立叶变换红外吡啶吸附光谱测定的。然后，该催化体系被用作一种高效催化剂，用于在室温下无溶剂热条件或超声辐照条件下，通过各种醛、邻苯二甲酸酐、氢氧化肼和二甲基酮的多组分和一锅反应合成 2H-吲唑并[2,1-b]酞嗪三酮类化合物。此外，该催化剂可轻松回收并重复使用，连续反应六个循环而不会明显丧失活性。
• Ultrasound-promoted catalyst-free one-pot four component synthesis of 2H-indazolo[2,1-b]phthalazine-triones in neutral ionic liquid 1-butyl-3-methylimidazolium bromide
  作者：Mohsen Shekouhy、Alireza Hasaninejad

  DOI：10.1016/j.ultsonch.2011.07.011

  日期：2012.3

  A catalyst-free one-pot four component methodology for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones under ultrasonic irradiation at room temperature using 1-butyl-3-methylimidazolium bromide, [Bmim]Br, as a neutral reaction medium is described. A broad range of structurally diverse aldehydes (aromatic aldehydes bearing electron withdrawing and/or electron releasing groups as well as heteroaromatic

  在室温下，以1-丁基-3-甲基咪唑鎓溴化物[Bmim] Br为原料，在室温下超声辐照下合成2H-吲唑并[2,1-b]酞嗪-三酮的无催化剂一锅四组分方法。描述了中性反应介质。已成功应用了多种结构多样的醛（带有吸电子和/或电子释放基团的芳族醛以及杂芳族醛），并以良好至极好的收率获得了相应的产物，而没有任何副产物。