2-(4-nitrophenyl)-3-(p-tolyl)thiazolidin-4-one

• 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: 2-(4-nitrophenyl)-3-(p-tolyl)thiazolidin-4-one
• 英文别名: 2-(4-nitrophenyl)-3-p-tolylthiazolidin-4-one；3-(4-Methylphenyl)-2-(4-nitrophenyl)-1,3-thiazolidin-4-one
• 化学式: C₁₆H₁₄N₂O₃S
• 分子量: 314.365
• InChiKey: AVWLSBMPINCXEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(4-nitrobenzylidene)-4-methylaniline 、 巯基乙酸 在 对甲苯磺酸 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 生成 2-(4-nitrophenyl)-3-(p-tolyl)thiazolidin-4-one
  参考文献：
  名称：

  Lawande; Arbad, Journal of the Indian Chemical Society, 2000, vol. 77, # 7, p. 352 - 354

  摘要：

  DOI：

文献信息

• Facile synthesis of 1,3-thiazolidin-4-ones as antitubercular agents
  作者：Dnyaneshwar D. Subhedar、Mubarak H. Shaikh、Manisha A. Arkile、Amar Yeware、Dhiman Sarkar、Bapurao B. Shingate

  DOI：10.1016/j.bmcl.2016.02.056

  日期：2016.4

  We have developed, highly efficient, one-pot, solvent-free, [Et3NH][HSO4] catalyzed multicomponent reaction protocol for the synthesis of 1,3-thiazolidin-4-ones in excellent yields. For the first time, the 1,3-thiazolidin-4-ones were evaluated in vitro for their antimycobacterial activity against Mycobacterium tuberculosis dormant MTB H37Ra and Mycobacterium bovis BCG strains. Among the synthesized

  我们已经开发出了一种高效，一锅，无溶剂，[Et 3 NH] [HSO 4 ]催化的多组分反应方案，用于以优异的产率合成1,3-噻唑烷酮-4-酮。首次在体外评估了1,3-噻唑烷酮-4-酮对休眠的结核分枝杆菌MTB H37Ra和牛分枝杆菌BCG菌株的抗分枝杆菌活性。在合成的碱性1,3-噻唑烷酮-4-酮中，尤其是化合物4c，4d，4e，4f，4h，4i和4j 显示出有希望的抗结核活性，并且对细胞系MCF-7，A549和HCT-116没有明显的细胞毒性。
• One-pot rapid synthesis of thiazole-substituted pyrazolyl-4-thiazolidinones mediated by diisopropylethylammonium acetate
  作者：Lalit D. Khillare、Manisha R. Bhosle、Amarsinh R. Deshmukh、Ramrao A. Mane

  DOI：10.1007/s11164-015-1940-6

  日期：2015.11

  A convenient one-pot, rapid and scalable synthetic protocol has been developed for recently reported anti-inflammatory agents, thiazole-substituted pyrazolyl-4-thiazolidinones. Quantitative multicomponent cyclocondensation of 3-(4-methyl-2-substituted thiazol-5-yl)-1-phenyl-1H-pyrazole-4-carbaldehydes (5a, b), amines and mercaptoacetic acid has been carried out in safer medium, diisopropylethylammonium acetate, at room temperature. The optimisation details of the developed novel protocol are recorded.

  一种方便的一锅法、快速且可扩展的合成方案已被开发，用于最近报道的抗炎药物，即噻唑取代的吡唑-4-噻唑烷酮。对3-(4-甲基-2-取代噻唑-5-基)-1-苯基-1H-吡唑-4-醛（5a, b）、胺和巯基乙酸的定量多组分环缩合反应已在更安全的介质二异丙基乙胺乙酸盐中于室温下进行。所开发的新型方案的优化细节已记录。
• 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。
• Ionic liquid mediated and promoted eco-friendly preparation of thiazolidinone and pyrimidine nucleoside–thiazolidinone hybrids and their antiparasitic activities
  作者：Xinying Zhang、Xiaoyan Li、Dongfang Li、Guirong Qu、Jianji Wang、Philippe M. Loiseau、Xuesen Fan

  DOI：10.1016/j.bmcl.2009.09.101

  日期：2009.11

  acid in [bmim][PF6]. The whole procedure is simple and straightforward and no aqueous work-up is needed. By employing this protocol, a series of novel pyrimidine nucleoside–thiazolidin-4-one hybrids were prepared and their preliminary antiparasitic activities were also studied and reported.

  在没有任何催化剂的情况下，通过醛，胺和巯基乙酸在[bmim] [PF 6 ]中的三组分反应，可以有效地合成2,3-二取代-1,3-噻唑烷-4-酮衍生物。整个过程简单明了，不需要水后处理。通过采用该方案，制备了一系列新型嘧啶核苷-噻唑烷-4-酮杂化物，并对其初步的抗寄生虫活性进行了研究和报道。
• Green synthesis of 1,3-Thiazolidin-4-ones derivatives by using acid-activated montmorillonite as catalyst
  作者：Mustafa M. Hasan AL-Abayechi、Abbas Al-nayili、Asim A. Balakit

  DOI：10.1016/j.inoche.2024.112076

  日期：2024.3

  methodology for synthesizing 1,3-Thiazolidin-4-one derivatives was developed. This method produced the target compounds in high yields and short reaction times by using solvent-free reaction conditions with heterogeneous catalysts, montmorillonite (MT) and acid-activated montmorillonite (acid-MT). MT and acid-MT were investigated in the synthesis using a variety of techniques, including conventional heat

  开发了一种环保、清洁、适用的1,3-噻唑烷-4-酮衍生物的合成方法。该方法采用无溶剂反应条件，采用非均相催化剂蒙脱石（MT）和酸活化蒙脱石（acid-MT），以高收率和短反应时间制备了目标化合物。使用多种技术（包括常规加热、超声波和微波辐射）对 MT 和酸-MT 的合成进行了研究，并研究了时间和温度两类因素。采用X射线衍射、N 2吸附-脱附、傅里叶变换红外光谱、扫描电子显微镜和透射电子显微镜对MT和酸-MT催化剂进行了表征。使用FTIR、1 H NMR、13 C NMR 和质谱来表征每种产物。环化步骤时间短、收率高，是影响所制备的催化剂acid-MT强度的最重要因素。此外，酸-MT催化剂易于回收，可重复使用多达五次，而催化活性不会大幅降低。