3-phenyl-2-(pyridin-2-yl)thiazolidin-4-one | 330849-10-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-phenyl-2-(pyridin-2-yl)thiazolidin-4-one
• 英文别名: 3-phenyl-2-(2-pyridinyl)thiazolidin-4-one；3-Phenyl-2-pyridin-2-yl-1,3-thiazolidin-4-one
• CAS: 330849-10-0
• 化学式: C₁₄H₁₂N₂OS
• 分子量: 256.328
• InChiKey: OSORQNPQHNSGNF-UHFFFAOYSA-N

物化性质

• 沸点：
  535.9±50.0 °C(Predicted)
• 密度：
  1.298±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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吡啶-2-甲醛 、 巯基乙酸 、 苯胺 在 layered double hydroxides poly(p-phenylenediamine) 作用下， 以 乙醇 为溶剂， 反应 5.5h， 以95%的产率得到3-phenyl-2-(pyridin-2-yl)thiazolidin-4-one
  参考文献：
  名称：

  绿色工具接枝聚对苯二胺作为催化剂一锅合成 1,3-噻唑烷-4-酮衍生物的缩合环化反应

  摘要：

  胺、羰基化合物和巯基乙酸之间的三组分反应现在被认为是合成 1,3-噻唑烷-4-酮的主要策略，它由以下步骤组成：（i）醛和胺的缩合反应亚胺的形成；(ii) 巯基乙酸和亚胺之间的反应，随后发生分子内环化反应，从而形成最终产物。这样，如果不使用合适的催化剂，反应就无法完成。因此，选择合适的催化剂对于成功合成这些化合物具有重要意义。在此，我们采用 LDHs@PpPDA 作为一种多功能催化剂，用于制备 1,3-thiazolidin-4-one 的新型衍生物。图形概要

  DOI：

  10.1080/17415993.2020.1812611

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。
• Silica chloride (SiO₂-Cl) catalyzed one pot synthesis of 2,3-disubstituted-thiazolidin-4-one
  作者：Kunal M. Gokhale、Vikas N. Telvekar

  DOI：10.1080/00397911.2020.1741641

  日期：2020.5.2

  Abstract In this paper, we report one-pot, three-component cyclo condensation of an aldehyde, an amine and thioglycolic acid to form 2,3-disubstituted-thiazolidin-4-one by using supported protic acid (Silica Chloride: SiO2-Cl) catalyst. The catalyst SiO2-Cl is compatible with a variety of aldehydes (aryl/heteroaryl) and the aromatic amines affording 2,3-disubstituted-thiazolidin-4-one analogs in 72–89%

  摘要 在本文中，我们报道了一种醛、胺和巯基乙酸的一锅三组分环缩合反应，通过使用负载的质子酸（二氧化硅：SiO2-Cl ) 催化剂。催化剂 SiO2-Cl 与多种醛（芳基/杂芳基）和芳香胺相容，以 72-89% 的产率提供 2,3-二取代-噻唑烷-4-one 类似物。此外，负载型催化剂可循环使用多次，催化活性没有显着损失。
• Visible-light-promoted C N and C S bonds formation: A catalyst and solvent-free photochemical approach for the synthesis of 1,3-thiazolidin-4-ones
  作者：Mohd Nazeef、Km Neha Shivhare、Shabir Ali、Khursheed Ansari、Mohd Danish Ansari、Saurabh K. Tiwari、Vikas Yadav、I.R. Siddiqui

  DOI：10.1016/j.jphotochem.2019.112347

  日期：2020.3

  A visible-light-induced, one-pot mild and efficient, multicomponent-tandem synthesis of diversified 1,3-thiazolidin-4-ones under catalyst and solvent-free conditions is reported. Here, visible-light, an ideal source of energy, has been used as photochemical activator to generate CN and CS bonds under radical mechanistic pathway from aromatic amines, aldehydes and thioglycolic acid. The reported methodology

  据报道，在无催化剂和无溶剂的条件下，可见光诱导的一锅式温和高效的多组分串联合成了多种1,3-噻唑烷酮-4-酮。在这里，可见光是一种理想的能源，已被用作光化学活化剂，通过自由基机制从芳族胺，醛和巯基乙酸生成C N和C S键。所报道的方法可以广泛地用于探索具有高选择性，短反应时间，对官能团的耐受性，成本效益和优异收率的1，3-噻唑烷丁-4-酮衍生物。
• One-pot sonochemical synthesis of 1,3-thiazolidin-4-ones using nano-CdZr4(PO4)6 as a robust heterogeneous catalyst
  作者：Javad Safaei-Ghomi、Maryam Navvab、Hossein Shahbazi-Alavi

  DOI：10.1016/j.ultsonch.2015.12.008

  日期：2016.7

  An efficient three-component synthesis of 1,3-thiazolidin-4-ones is described by one-pot condensation of aldehydes, aniline and thioglycolic acid with nano-CdZr4(PO4)6 as a robust heterogeneous catalyst under ultrasonic irradiation. Use of simple and readily available starting materials, experimental simplicity, applying the sonochemical methodology as an efficient method and innocuous means of activation

  在超声波辐射下，通过一锅缩合醛，苯胺和巯基乙酸与纳米CdZr4（PO4）6作为强健的多相催化剂，描述了一种有效的三组分合成1,3-噻唑烷-4-酮的方法。该协议的一些优点是使用简单易得的起始原料，简化实验，将声化学方法学用作一种有效方法以及在合成化学中使用无害的活化方法是该协议的一些优势。
• Preparation and characterization of Fe₃O₄@SiO₂/APTPOSS core-shell composite nanomagnetics as a novel family of reusable catalysts and their application in the one-pot synthesis of 1,3-thiazolidin-4-one derivatives
  作者：Javad Safaei-Ghomi、Seyed Hadi Nazemzadeh、Hossein Shahbazi-Alavi

  DOI：10.1002/aoc.3520

  日期：2016.11

  The inorganic–organic hybrid polyhedral oligomeric silsesquioxane magnetic nanoparticles were used as an efficient new heterogeneous catalyst for the one‐pot three‐component synthesis of 1,3‐thiazolidin‐4‐ones under solvent‐free conditions. Moreover, these nanoparticles could be easily separated using an external magnet and then reused several times without significant loss of catalytic activity. Copyright

  制备了以多面体低聚倍半硅氧烷衍生物形式的八[[（3-（3-氨基丙基三乙氧基硅烷）丙基]十八碳倍半硅氧烷（APTPOSS），并用作先驱试剂，以磁性氧化铁纳米粒子为核心，无机-有机为新型壳-壳复合材料杂多面体低聚倍半硅氧烷为壳。铁3 O 4 @SiO 2/ APTPOSS已通过傅立叶变换红外光谱法，扫描电子显微镜，能量色散光谱法，动态光散射，热重分析，X射线衍射和振动样品磁力分析法得到证实。无机-有机杂化多面体低聚倍半硅氧烷磁性纳米颗粒被用作一种高效的新型非均相催化剂，用于在无溶剂条件下单锅三组分合成1,3-噻唑烷酮-4-酮。此外，这些纳米颗粒可以使用外部磁体轻松分离，然后重复使用几次，而不会显着降低催化活性。版权所有©2016 John Wiley＆Sons，Ltd.