3-(1H-benzo[d]imidazol-2-yl)-2-phenylthiazolidin-4-one | 84257-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 3-(1H-benzo[d]imidazol-2-yl)-2-phenylthiazolidin-4-one
• 英文别名: 3-(1H-Benzimidazol-2-yl)-2-phenyl-1,3-thiazolidin-4-one
• CAS: 84257-86-3
• 化学式: C₁₆H₁₃N₃OS
• 分子量: 295.365
• InChiKey: KLHFGZWERGVLCH-UHFFFAOYSA-N

物化性质

• 熔点：
  232 °C
• 沸点：
  547.4±60.0 °C(Predicted)
• 密度：
  1.407±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  巯基乙酸 、 (E)-N-(1H-benzo[d]imidazol-2-yl)-1-phenylmethanimine 生成 3-(1H-benzo[d]imidazol-2-yl)-2-phenylthiazolidin-4-one
  参考文献：
  名称：

  ABDEL-RAHMAN, A. E.;MAHMOUD, A. M.;EL-NAGGAR, G. M.;EL-SHERIFF, H. A., PHARMAZIE, 1983, 38, N 9, 589-590

  摘要：

  DOI：

文献信息

• Supported protic acid-catalyzed synthesis of 2,3-disubstituted thiazolidin-4-ones: enhancement of the catalytic potential of protic acid by adsorption on solid supports
  作者：Dinesh Kumar、Mukesh Sonawane、Brahmam Pujala、Varun K. Jain、Srikant Bhagat、Asit K. Chakraborti

  DOI：10.1039/c3gc41218k

  日期：——

  The catalytic potential of various protic acids has been assessed for the one pot tandem condensation–cyclisation reaction involving an aldehyde, an amine, and thioglycolic acid to form 2,3-disubstituted thiazolidin-4-ones. The catalytic potential of the various protic acids that follows the order TfOH > HClO4 > H2SO4 ∼ p-TsOH > MsOH ∼ HBF4 > TFA ∼ AcOH is improved significantly by adsorption on solid supports, in particular using silica gel (230–400 mesh size), with the resulting relative catalytic potential following the order HClO4–SiO2 > TfOH–SiO2 ≫ H2SO4–SiO2 > p-TsOH–SiO2 > MsOH–SiO2 ∼ HBF4–SiO2 > TFA–SiO2 ∼ HOAc–SiO2. The better catalytic potential of HClO4–SiO2 as compared to that of Tf–SiO2, although TfOH is a stronger protic acid than HClO4, can be rationalised through a transition state model depicting the interaction of the individual protic acid with SiO2. The catalytic efficiency of HClO4 adsorbed on various solid supports was in the order HClO4–SiO2 ≫ HClO4–K10 > HClO4–KSF > HClO4–TiO2 ∼ HClO4–Al2O3. The catalytic system HClO4–SiO2 is compatible with different variations of aldehydes (aryl/heteroaryl/alkyl/cycloalkyl) and the amines (aryl/heteroaryl/arylalkyl/alkyl/cycloalkyl) affording the desired 2,3-disubstituted thiazolidin-4-ones in 70–87% yields (43 examples). The electronic and the steric factors associated with the aldehydes and the amines provide a handle for selective thiazolidinone formation and were found to be dependent on the extent of imine formation. No significant amount of thiazolidinone formation took place during the reaction of the preformed amide (synthesised from the amine and thioglycolic acid) with benzaldehyde suggesting that the reaction proceeds through the initial reversible imine formation followed by cyclocondensation of the preformed imine with thioglycolic acid, the reversible imine formation being the determining step to control selectivity of thiazolidinone formation in competitive environments. The feasibility of a large scale reaction and catalyst recycling/reuse is demonstrated.

  已对各种质子酸的催化潜能进行了评估，这些质子酸用于涉及醛、胺和巯基乙酸的一锅法串联缩合-环化反应，以形成2,3-二取代的噻唑烷-4-酮。通过吸附在固体载体上，特别是使用硅胶（230-400目大小），可以显著提高各种质子酸的催化潜能，这些质子酸的催化潜能顺序为：TfOH > HClO4 > H2SO4 ∼ p-TsOH > MsOH ∼ HBF4 > TFA ∼ AcOH。所得相对催化潜能的顺序为：HClO4–SiO2 > TfOH–SiO2 ≫ H2SO4–SiO2 > p-TsOH–SiO2 > MsOH–SiO2 ∼ HBF4–SiO2 > TFA–SiO2 ∼ HOAc–SiO2。与Tf–SiO2相比，HClO4–SiO2具有更好的催化潜能，尽管TfOH是一种比HClO4更强的质子酸，这可以通过描述单个质子酸与SiO2相互作用的过渡态模型来合理化。HClO4吸附在各种固体载体上的催化效率顺序为：HClO4–SiO2 ≫ HClO4–K10 > HClO4–KSF > HClO4–TiO2 ∼ HClO4–Al2O3。催化系统HClO4–SiO2与不同变体的醛（芳基/杂芳基/烷基/环烷基）和胺（芳基/杂芳基/芳基烷基/烷基/环烷基）兼容，以70-87%的产率（43个例子）提供所需的2,3-二取代噻唑烷-4-酮。与醛和胺相关的电子和空间因素为选择性噻唑烷酮的形成提供了依据，并发现它们依赖于亚胺形成的程度。在预形成的酰胺（由胺和巯基乙酸合成）与苯甲醛的反应中，没有发生显著量的噻唑烷酮形成，这表明反应通过初始的可逆亚胺形成，然后是预形成的亚胺与巯基乙酸的环化缩合，可逆的亚胺形成是控制竞争环境中的噻唑烷酮形成选择性的决定步骤。大规模反应的可行性以及催化剂的回收/再利用得到了证明。
• Design of a new multi-functional catalytic system Ni/SO₃H@zeolite-Y for three-component synthesis of <i>N</i>-benzo-imidazo- or -thiazole-1,3-thiazolidinones
  作者：Mehdi Kalhor、Soodabeh Banibairami

  DOI：10.1039/d0ra08237f

  日期：——

  three-component synthesis of 3-benzimidazolyl-1,3-thiazolidin-4-ones and new 3-benzthiazoleyl-1,3-thiazolidin-4-ones via cyclocondensation of 2-aminobenzimidazole or 2-aminobenzothiazole, aromatic aldehydes and thioglycolic acid in acetone–H2O at room temperature. This economical chemical procedure has advantages such as excellent yield in short reaction times, convenient manipulation and high purity of products

  在这项研究中，合成了一种纳米多孔沸石-NaY 负载的磺酸，并成功地将 Ni( II ) 离子稳定在 SO 3 H@zeolite-Y (Ni/SO 3 H@zeolite-Y) 上。这种新型沸石纳米复合材料使用多种技术进行了表征，包括 FT-IR、FE-SEM、TGA、BET 和 EDX。Ni/SO 3 H@zeolite-Y作为多功能高活性纳米催化剂用于三组分合成3-苯并咪唑基-1,3-噻唑烷-4-酮和新型3-苯并噻唑基-1,3-噻唑烷-4-酮通过2-氨基苯并咪唑或 2-氨基苯并噻唑、芳香醛和巯基乙酸在丙酮-H 2中的环缩合O 在室温下。这种经济的化学过程具有反应时间短、收率高、操作方便、产品纯度高、适用于广泛的底物、使用无毒的多相酸催化剂、重复使用性好等优点。
• A one-pot multi-component reaction for the facile synthesis of some novel 2-aryl thiazolidinones bearing benzimidazole moiety using La(NO3)3·6H2O as an efficient catalyst
  作者：Mehdi Kalhor、Soodabeh Banibairami、Seyed Ahmad Mirshokraie

  DOI：10.1007/s11164-017-2974-8

  日期：2017.11

  synthesized via a rapid, one-pot, three-component reaction by using La(NO3)3·6H2O as an efficient catalyst from the reaction of 2-aminobenzimidazole, aromatic aldehydes and thioglycolic acid in ethanol at room temperature. These new compounds were characterized by IR, 1H, 13C NMR and mass spectroscopies. An inexpensive and available catalyst, short reaction time, easy workup, good to excellent yields

  利用La（NO 3）3 ·6H 2 O作为高效催化剂，通过快速的一锅三组分反应合成了一系列3-benzimidazolyl-2-aryl thiazolidinones，4a–j的新衍生物。室温下2-氨基苯并咪唑，芳香醛和巯基乙酸在乙醇中的反应 这些新化合物的特征在于IR，1 H，13 C NMR和质谱。该反应的优点是廉价且可得到的催化剂，反应时间短，易于后处理，良好至优异的收率和无毒溶剂。
• Synthesis of Thiazolidin-4-ones Using Novel Magnetic Nanoparticles Modified with S-Proline
  作者：Leila Zare Fekri

  DOI：10.1080/00304948.2021.1908045

  日期：2021.7.4
• ABDEL-RAHMAN, A. E.;MAHMOUD, A. M.;EL-NAGGAR, G. M.;EL-SHERIFF, H. A., PHARMAZIE, 1983, 38, N 9, 589-590
  作者：ABDEL-RAHMAN, A. E.、MAHMOUD, A. M.、EL-NAGGAR, G. M.、EL-SHERIFF, H. A.

  DOI：——

  日期：——