methyl 6-amino-4-(4-bromophenyl)-5-cyano-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylate | 1400891-60-2

• 分子结构分类: 有机化合物
• 英文名称: methyl 6-amino-4-(4-bromophenyl)-5-cyano-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylate
• CAS: 1400891-60-2
• 化学式: C₁₅H₁₁BrN₄O₃
• 分子量: 375.181
• InChiKey: BGAXZEHNNABBOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对溴苯甲醛 、 丁炔二酸二甲酯 、 丙二腈 在 hydrazine hydrate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以94%的产率得到methyl 6-amino-4-(4-bromophenyl)-5-cyano-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylate
  参考文献：
  名称：

  六亚甲基四胺官能化磁性纳米粒子的制备，表征及其作为吡喃并吡唑衍生物合成的新型催化剂的应用

  摘要：

  通过在涂有二氧化硅的Fe 3 O 4磁性纳米粒子表面上的硅烷醇基与（3-氯丙基）三乙氧基硅烷，然后六亚甲基四胺和氯磺酸反应，制备了一种新的磁性催化剂。使用热重分析，振动样品磁力分析，扫描电子显微镜和能量分散X射线分析对获得的磁性催化剂进行表征。在吡喃并吡唑化合物的合成中对其催化活性进行了研究，结果表明该产物的收率高，反应时间短。

  DOI：

  10.1002/aoc.4025

文献信息

• A green and convenient approach for the synthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates via a one-pot, multi-component reaction in water
  作者：Adeleh Moshtaghi Zonouz、Issa Eskandari、Hamid Reza Khavasi

  DOI：10.1016/j.tetlet.2012.08.010

  日期：2012.10

  A green and efficient one-pot, four-component synthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates in water is described. The method is catalyst-free, atom-economical, and does not involve tedious work-up or purification affording the target compounds in good yields.

  描述了一种绿色高效的一锅四组分甲基6-氨基-5-氰基-4-芳基-2,4-二氢吡喃并[2,3 - c ]吡唑-3-羧酸酯的合成方法。该方法是无催化剂的，原子经济的，并且不涉及繁琐的后处理或纯化，从而以良好的收率提供了目标化合物。
• Environmentally benign synthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-<i>c</i>]pyrazole-3-carboxylates using CeO₂ nanoparticles as a reusable and robust catalyst
  作者：Javad Safaei-Ghomi、Mehrnoosh Asgari-Kheirabadi、Hossein Shahbazi-Alavi

  DOI：10.1515/znb-2016-0119

  日期：2016.11.1

  In this work, we report the synthesis and characterization of CeO₂ nanoparticles as an efficient catalyst for the preparation of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates via one-pot four-component condensation reaction of dimethyl acetylenedicarboxylate, hydrazine hydrate, malononitrile, and aldehydes in aqueous medium. The use of a non-hazardous organic solvent, easy recovery of the catalyst, compatibility with various functional groups, and high yield of the products make the protocol attractive, greener, and economic.

  在这项工作中，我们报道了CeO2纳米颗粒的合成和表征，作为一种高效催化剂，用于在水性介质中通过一锅四组分缩合反应制备甲基6-氨基-5-氰基-4-芳基-2,4-二氢吡喃并[2,3-c]吡唑-3-羧酸酯。使用无危害的有机溶剂、易于回收的催化剂、与各种功能团的兼容性以及高产率的产品使该方案具有吸引力、绿色和经济的特点。
• Novel iron doped calcium oxalates as promising heterogeneous catalysts for one-pot multi-component synthesis of pyranopyrazoles
  作者：Kranthi Kumar Gangu、Suresh Maddila、Surya Narayana Maddila、Sreekantha B. Jonnalagadda

  DOI：10.1039/c6ra25372e

  日期：——

  Fe-CaOx materials proved excellent as catalysts in the one-pot syntheses of eight 2,4-dihydro pyrano[2,3-c]pyrazole derivatives via four component condensation of aromatic aldehydes, malononitrile, hydrazine hydrate and dimethyl acetylenedicarboxylate in ethanol with impressive yields (92–98%) in short reaction times (<20 min). The 2.0 mmol loaded iron in Fe-CaOx showed the finest catalytic performance

  在设计铁掺杂草酸钙（Fe-CaOx）时，采用了使用表面改性剂谷氨酸的共沉淀方法。制备了具有多种铁负载量（0.5-3.0 mmol）的Fe-CaOx，并通过X射线粉末衍射（XRD），傅立叶变换红外光谱（FT-IR），电子显微镜（SEM，TEM）检查了它们的相纯度和表面特征，能量色散X射线（EDX），电感耦合等离子体发射光谱（ICP-OES），N 2吸收，热和荧光分析。该Fe-CaOx材料证明优良如八-2,4-二氢吡喃并[2,3-一锅合成催化剂Ç ]吡唑衍生物通过在较短的反应时间（<20分钟）内，芳族醛，丙二腈，水合肼和乙炔二甲酸二甲酯在乙醇中的四组分缩合反应具有令人印象深刻的收率（92-98％）。与其他负载相比，Fe-CaOx中的2.0 mmol负载铁表现出最佳的催化性能，在10分钟内的收率为98％。Fe-CaOx的稳定性，易分离性和多达六个循环的可重复使用性使其成为增值有机转化的环保且具有成本效益的可行选择。
• Synthesis, characterisation and catalytic activity of 4, 5-imidazoledicarboxylate ligated Co(II) and Cd(II) metal-organic coordination complexes
  作者：Kranthi Kumar Gangu、Suresh Maddila、Saratchandra Babu Mukkamala、Sreekantha B. Jonnalagadda

  DOI：10.1016/j.molstruc.2017.04.083

  日期：2017.9

  7°]. While Co(II) in 1 exhibited a six coordination geometry with 4,5-Imdc and water molecules, Cd(II) ion in 2 showed a seven coordination with the same ligand and solvent. In both 1 and 2, the hydrogen bond interactions with mononuclear unit generated 3D-supramolecular structures. Both complexes exhibit solid state fluorescent emission at room temperature. The efficacy of both the complexes as heterogeneous

  摘要 构建了两种单核配位配合物[Co(4,5-Imdc)2 (H2O)2] (1)和[Cd(4,5-Imdc)2( )3]· (2)使用 Co(II) 和 Cd(II) 金属盐和 4,5-咪唑二羧酸 (4,5-Imdc) 作为有机配体。1、2均通过单晶XRD结构表征，结果表明1属于P21/n空间群，晶胞参数[a = 5.0514(3) A, b = 22.5786(9) A, c = 6.5377(3 ) A, β = 111.5°] 而, 2 属于具有晶胞参数的 P21/c 空间群 [a = 6.9116(1) A, b = 17.4579(2) A, c = 13.8941(2) A, β = 97.7 °]。虽然 1 中的 Co(II) 显示出具有 4,5-Imdc 和水分子的六配位几何结构，但 2 中的 Cd(II) 离子显示出与相同配体和溶剂的七次配位。在 1 和 2 中，与单核单元的氢键相互作用产生了
• Uncapped SnO2 quantum dot catalyzed cascade assembling of four components: a rapid and green approach to the pyrano[2,3-c]pyrazole and spiro-2-oxindole derivatives
  作者：Sanjay Paul、Koyel Pradhan、Sirshendu Ghosh、S.K. De、Asish R. Das

  DOI：10.1016/j.tet.2014.02.077

  日期：2014.9

  A new uncapped SnO2 quantum dots (QDs) catalyzed strategy for the synthesis of substituted pyrano [2,3-c]pyrazole and spiro-2-oxindole derivatives has been developed via a multicomponent one pot approach in aqueous medium. The reactions can be performed at low catalyst loadings with excellent functional group tolerance. This communication also reports a comparative study of the efficiency related to the catalytic activity of uncapped SnO2 QDs, oleic acid capped SnO2 QDs, and SnO2 nanoflower. Uncapped SnO2 QDs, capped SnO2 QDs, and SnO2 nanoflower were prepared by simple solvothermal method and characterized by XRD, FESEM, and TEM images. The easy recovery of the catalyst and high yield of the products make the protocol attractive, sustainable, and economic. The catalyst was reused for six cycles with almost unaltered catalytic activity. (C) 2014 Elsevier Ltd. All rights reserved.