N-phenyl-5-(pyridin-2-yl)-1,3,4-oxadiazol-2-amine | 60838-23-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-phenyl-5-(pyridin-2-yl)-1,3,4-oxadiazol-2-amine
• 英文别名: N-phenyl-(5-pyridin-2-yl)[1,3,4]oxadiazole-2-yl-amine；2-benzyl-5-(pyridin-2-yl)-1,3,4-oxadiazole；2-anilino-5-(2-pyridyl)-1,3,4-oxadiazole；N-phenyl-5-pyridin-2-yl-1,3,4-oxadiazol-2-amine
• CAS: 60838-23-5
• 化学式: C₁₃H₁₀N₄O
• 分子量: 238.249
• InChiKey: CSOJDZMPMIGBCH-UHFFFAOYSA-N

物化性质

• 熔点：
  230-231 °C(Solv: toluene (108-88-3))
• 沸点：
  422.0±37.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-picolinoyl-4-phenyl-3-thiosemicarbazide 在 potassium hydrogensulfate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 生成 N-phenyl-5-(pyridin-2-yl)-1,3,4-oxadiazol-2-amine
  参考文献：
  名称：

  KHSO4 介导的 2-amino-1,3,4-oxadiazole 衍生物的简易合成

  摘要：

  通过苯甲酰肼和异硫氰酸酯衍生物的环化脱硫，建立了一种新型、高效且温和的 KHSO 4介导的 2-氨基-1,3,4-恶二唑合成方法。反应在室温下顺利进行，并以中等至良好的收率产生相应的产物。该协议还显示出良好的官能团耐受性。

  DOI：

  10.1016/j.tet.2021.132382

文献信息

• NNS tridentate thiosemicarbazide and 1,3,4-thiadiazole-2-amine complexes of some transition metal ions: syntheses, structure and fluorescence properties
  作者：A. Bharti、Pooja Bharati、N.K. Singh、M.K. Bharty

  DOI：10.1080/00958972.2016.1160074

  日期：2016.4.2

  1,3,4-thiadiazole-2-amine (1) formed [Zn(2-Hppt)2(OAc)2] (6) and [Cd2(2-Hppt)2(OAc)2(μ-OAc)2] (7) in which Cd(II) has a binuclear acetate-bridged seven coordinate pentagonal bipyramidal geometry. Complex 7 is also a fluorescent material with maximum emission at 425 nm at an excitation wavelength of 254 nm.

  摘要 Zn(II)、Mn(II) 和 Ni(II) 醋酸盐与 1-吡啶甲酰基-4-苯基-3-氨基硫脲 (Hppts) 反应生成 [Zn(ppts)2]·CHCl3 (3), [ Mn(ppts)2]·THF(4)和[Ni(ppts)2]·THF(5)，但HgCl2得到环化产物N-苯基-5-(吡啶-2-基)-1， 3,4-恶二唑-2-基-胺(2)。用浓度治疗 Hppts。H2SO4 形成 N-苯基-5-(吡啶-2-基)-1,3,4-噻二唑-2-基-胺 (1)。Hppts 是一种非荧光材料，但 3, 4 和环化产物 1,3,4-恶二唑/1,3,4-噻二唑是荧光材料。环化配体 N-苯基-5-(吡啶-2-基)-1,3,4-噻二唑-2-胺 (1) 形成 [Zn(2-Hppt)2(OAc)2] (6) 和 [ Cd2(2-Hppt)2(OAc)2(μ-OAc)2] (7) 其中 Cd(II) 具有双核醋酸桥连的七坐标五边形双锥几何。
• Efficient one-pot synthesis of substituted 2-amino-1,3,4-oxadiazoles
  作者：Eugene L. Piatnitski Chekler、Hassan M. Elokdah、John Butera

  DOI：10.1016/j.tetlet.2008.09.057

  日期：2008.11

  A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles has been developed. The method is a significant improvement over previously reported syntheses. Reaction of carboxylic acids with thiosemicarbazides afforded the corresponding oxadiazoles in moderate to good yields. In general, the products precipitated from the reaction mixture, and were collected by filtration. In most of the cases, no chromatographic separations were required. To explore the scope and limitations of this reaction, various aliphatic, aromatic, and heteroaromatic carboxylic acids were reacted with different substituted thiosemicarbazides. The influence of R-1 and R-2 substituents on the reaction yield and additional results demonstrating the versatility of this method are presented. (c) 2008 Elsevier Ltd. All rights reserved.
• Tetrazoles: LV. Perparation of 2-anilino-5-aryl(hetaryl)-1,3,4-oxadiazoles from 5-substituted tetrazoles under microwave activation
  作者：Yu. A. Efimova、G. G. Karabanovich、T. V. Artamonova、G. I. Koldobskii

  DOI：10.1134/s1070428009080211

  日期：2009.8

  In reaction of 5-aryl(hetaryl)tetrazoles with phenyl isocyanate under the conditions of microwave activation the corresponding 2-anilino-5-aryl(hetaryl)-1,3,4-oxadiazoles formed in high yields. The application of the microwave activation fourfold reduced the reaction time.
• Prabhu, Girish; Madhu, Chilakapathi; Sureshbabu, Vommina V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 7, p. 865 - 870
  作者：Prabhu, Girish、Madhu, Chilakapathi、Sureshbabu, Vommina V.

  DOI：——

  日期：——
• A KHSO4 mediated facile synthesis of 2-amino-1,3,4-oxadiazole derivatives
  作者：Binyu Long、Binghua Tian、Qiang Tang、Xiangnan Hu、Lei Han、Zifan Wang、Chenyu Wang、Yue Wu、Yu Yu、Zongjie Gan

  DOI：10.1016/j.tet.2021.132382

  日期：2021.9

  A novel, efficient and mild KHSO4 mediated synthesis for 2-amino-1,3,4-oxadiazoles has been established via the cyclodesulfurization of benzoylhydrazine and isothiocyanate derivatives in one pot. The reactions proceeded smoothly at room temperature and produced corresponding products in moderate to good yields. This protocol also showed good functional group tolerance.

  通过苯甲酰肼和异硫氰酸酯衍生物的环化脱硫，建立了一种新型、高效且温和的 KHSO 4介导的 2-氨基-1,3,4-恶二唑合成方法。反应在室温下顺利进行，并以中等至良好的收率产生相应的产物。该协议还显示出良好的官能团耐受性。