5-Benzylidenamino-4-phenyl-pyrimidazol | 80493-73-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Benzylidenamino-4-phenyl-pyrimidazol
• 英文别名: benzylidene-(2-phenyl-imidazo[1,2-a]pyridin-3-yl)-amine；1-phenyl-N-(2-phenylimidazo[1,2-a]pyridin-3-yl)methanimine
• CAS: 80493-73-8
• 化学式: C₂₀H₁₅N₃
• 分子量: 297.359
• InChiKey: CEECUFSVAZYHSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  sodium hydroxy(phenyl)methanesulfonate 以 乙醇 为溶剂， 反应 9.0h， 生成 5-Benzylidenamino-4-phenyl-pyrimidazol
  参考文献：
  名称：

  Astik, R. R.; Thaker, K. A., Journal of the Indian Chemical Society, 1981, vol. 58, p. 1013 - 1014

  摘要：

  DOI：

文献信息

• Application of Triphenylammonium Tricyanomethanide as an Efficient and Recyclable Nanostructured Molten-Salt Catalyst for the Synthesis of N-Benzylidene-2-arylimidazo[1,2-a]pyridin-3-amines
  作者：Saeed Baghery、Mohammad Zolfigol、Romana Schirhagl、Masoumeh Hasani

  DOI：10.1055/s-0036-1558965

  日期：2017.6

  Triphenylammonium tricyanomethanide (Ph3NH)[C(CN)3] was synthesized and used as an efficient and recyclable nanostructured molten-salt (NMS) catalyst for the synthesis of N-benzylidene-2-arylimidazo[1,2-a]pyridin-3-amines by the reaction of various (het)aryl aldehydes with trimethylsilyl cyanide and pyridin-2-amine under solvent-free conditions at 50 °C. The NMS catalyst could be simply recycled and reused several times without significant loss of its catalytic activity.

  三苯基铵三氰甲烷基化物(Ph3NH)[C(CN)3]被合成并用作高效可回收的纳米结构熔盐(NMS)催化剂，用于在50°C的无溶剂条件下，通过各种(杂)芳香醛与三甲基硅氰和吡啶-2-胺的反应合成N-苄基亚甲基-2-芳基咪唑并[1,2-a]吡啶-3-胺。NMS催化剂可以简单回收和多次重复使用，而不会显著降低其催化活性。
• A chemoselective Ugi-type reaction in water using TMSCN as a functional isonitrile equivalent: generation of heteroaromatic molecular diversity
  作者：Sankar Kumar Guchhait、Vikas Chaudhary、Chetna Madaan

  DOI：10.1039/c2ob26733k

  日期：——

  KF-mediated nucleophilic activation of TMSCN as a functional isonitrile equivalent establishes an efficient and chemoselective Ugi-type multicomponent reaction of a heterocyclic amidine and aldehyde with TMSCN in water. In this approach, the use of isocyanide is circumvented, known competing reactions are virtually eliminated, pure products are obtained by a non-chromatographic method, and therapeutically relevant and diverse N-fused 3-aminoimidazoles can be prepared from a wide variety of aldehydes and heterocyclic amidines. This reaction coupling with cascade cyclization provides various privileged tetracyclic heteroaromatic scaffolds.

  KF催化的TMSCN亲核活化作为功能性异腈等价物，建立了羟基胺和醛与TMSCN在水中进行的高效且化学选择性的Ugi类型多组分反应。在这种方法中，避免了异氰酸酯的使用，已知的竞争反应几乎被消除，纯产品通过非色谱法获得，并且可从多种醛和杂环胺制备出具有治疗相关性和多样性的N-融合3-氨基咪唑。该反应结合级联环化提供了多种特权的四环杂芳烃骨架。
• BF₃/MCM-41 as nano structured solid acid catalyst for the synthesis of 3-iminoaryl-imidazo[1,2-a]pyridines
  作者：Mohammad Abdollahi-Alibeik、Ali Rezaeipoor-Anari

  DOI：10.1039/c3cy00947e

  日期：——

  of aldehydes, 2-aminopyridines and trimethylsilyl cyanide was carried out in the presence of MCM-41 supported boron trifluoride (BF3/MCM-41) as a nanostructured solid acid catalyst for the synthesis of 3-iminoaryl-imidazo[1,2-a]pyridine derivatives. MCM-41 nanoparticles were synthesized by a sol–gel method and BF3/MCM-41 samples with various loading amounts of BF3 and different calcination temperatures

  在MCM-41负载的三氟化硼（BF 3 / MCM-41）作为用于合成3-亚氨基芳基的纳米结构固体酸催化剂的存在下，进行了各种类型的醛，2-氨基吡啶和三甲基甲硅烷基氰化物的多组分反应。-咪唑并[1,2-a]吡啶衍生物。通过溶胶-凝胶法合成了MCM-41纳米粒子，并通过XRD，SEM和FT-IR技术制备了具有不同BF 3上样量和不同煅烧温度的BF 3 / MCM-41样品。催化性能实验表明，BF 3在400°C下煅烧的/ MCM-41具有最佳的催化活性。可回收性和可重复使用性实验表明，该催化剂可重复使用多次，且活性适度降低。
• An efficient synthesis of 3-amino-2-arylimidazo[1,2-a]pyridines
  作者：Mehdi Adib、Esmail Sheibani、Long-Guan Zhu、Peiman Mirzaei

  DOI：10.1016/j.tetlet.2008.05.134

  日期：2008.8

  An efficient synthesis of 3-amino-2-arylimidazo[1,2-a]pyridines is described via a novel multicomponent reaction between 2-aminopyridines, benzaldehydes and imidazoline-2,4,5-trione under solvent-free conditions. (c) 2008 Elsevier Ltd. All rights reserved.