5-(4-methylphenyl)-1,2,4-triazolidine-3-thione

• 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: 5-(4-methylphenyl)-1,2,4-triazolidine-3-thione
• 英文别名: 5-p-tolyl-[1,2,4]triazolidine-3-thione；5-(4-Methylphenyl)-1,2,4-triazolidine-3-thione
• 化学式: C₉H₁₁N₃S
• 分子量: 193.272
• InChiKey: WXRWXHCBXGTEIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  68.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 在 氨基磺酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.58h， 生成 5-(4-methylphenyl)-1,2,4-triazolidine-3-thione
  参考文献：
  名称：

  A novel one pot multi-component strategy for facile synthesis of 5-aryl-[1,2,4]triazolidine-3-thiones

  摘要：

  We have disclosed an efficient, one pot, novel multi-component approach for the synthesis of 5-aryl-[1,2,4]triazolidine-3-thiones from aldehyde, hydrazine hydrate, and trimethylsilyl isothiocyanate (TMSNCS) in the presence of catalytic amount of sulfamic acid. High yields, easy work-up procedure, no chromatographic separation, and novelty in multi-component strategy are the main merits of the present strategy. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2014.10.052

文献信息

• Synthesis of triazolidines and triazole using DMAP
  作者：Devidas A. Mali、Vikas N. Telvekar

  DOI：10.1080/00397911.2016.1263338

  日期：2017.2.16

  ABSTRACT An efficient methodology has been developed for the synthesis of 1,2,4-triazolidine-3-thione and 3-ethoxy-5-phenyl-4H-1,2,4 triazole using N,N-dimethylpyridine-4-amine (DMAP). Aldehydes and thiosemicarbazide were reacted in water at ambient temperature in presence of DMAP and provided corresponding products in good to moderate yield. GRAPHICAL ABSTRACT

  摘要 开发了一种使用 N,N-二甲基吡啶-4-胺合成 1,2,4-三唑烷-3-硫酮和 3-乙氧基-5-苯基-4H-1,2,4 三唑的有效方法（ DMAP）。醛和氨基硫脲在环境温度下在 DMAP 存在下在水中反应，并以良好至中等产率提供相应的产物。图形概要
• L-Proline Nitrate: An Efficient Amino Acid Ionic Liquid Catalyzed Synthesis of 5-aryl-[1, 2, 4]-triazolidine-3-thiones
  作者：Dattaprasad M. Pore、Suraj A. Sonawane

  DOI：10.2174/1570178619666220128141519

  日期：2022.9

  An environmentally benign, simple, rapid synthesis of 1,2,4-triazolidine-3-thiones at room temperature is reported using amino acid-derived Brønsted acidic ionic liquid L-proline nitrate [Pro+NO3 -] from aldehyde and thiosemicarbazide in an aqueous medium. A cost-effective and energy-efficient catalyst with the reusability of up to five cycles without significant loss in the catalytic activity makes this protocol superior. A faster reaction and easy work-up with excellent yields are the added advantages of this protocol.

  摘要：报道了一种在室温下使用氨基酸衍生的Brønsted酸性离子液体L-脯氨酸硝酸盐[Pro+NO3-]从醛和硫脲中合成1,2,4-三唑烷-3-硫酮的环境友好、简单、快速的方法。这种成本效益高、能源效率高的催化剂可重复使用五个周期而不会显著降低催化活性，更快的反应速度和易于操作的良好收率是这种方法的附加优点。
• Green and Efficient Synthesis of 1, 2, 4-Triazolidine-3-thiones using Guanidine Hydrochloride as a Recyclable Catalyst under the Aqueous Condition
  作者：Vikas N. Telvekar、Angad B. Barkule、Yatin U. Gadkari

  DOI：10.2174/1570178619666220111110352

  日期：2022.9

  A rapid and highly efficient methodology for the synthesis of 1, 2, 4-triazolidine-3-thiones derivatives has been developed in the presence of a catalytic amount of guanidine hydrochloride using water as a solvent. The reaction of thiosemicarbazide with different aryl aldehydes resulted in the formation of title compounds in good yields (85-95%) with a convenient reaction time (20-30 min). The key advantages of this approach include shorter reaction time, energy efficiency, easy work-up procedure, and wide substrate scope tolerance. Furthermore, the catalyst was recycled without significant loss of its catalytic activity.

  摘要：在水溶剂存在催化剂氯化胍的情况下，开发了一种快速和高效的合成1,2,4-三唑啉-3-硫酮衍生物的方法。硫脲与不同的芳基醛反应，以良好的收率（85-95%）形成了目标化合物，反应时间方便（20-30分钟）。这种方法的关键优势包括反应时间短，能源效率高，易于操作，底物范围宽。此外，催化剂可循环使用，而且不会明显损失其催化活性。
• An efficient and expeditious synthesis of 1,2,4-triazolidine-3-thiones using meglumine as a reusable catalyst in water
  作者：Liklesha B Masram、Simren S Salim、Angad B Barkule、Yatin U Gadkari、Vikas N Telvekar

  DOI：10.1007/s12039-022-02087-5

  日期：——

  times, mild reaction conditions, easy workup, simple purification procedures, water as a solvent, and wide substrate scope tolerance. Further, the catalyst was recycled (up to 4 cycles) without compromising the yield of the final products. Graphical abstract The current protocol demonstrates the synthesis of 1,2,4-triazolidine-3-thiones from variously substituted aldehydes or ketones with thiosemicarbazide

  以葡甲胺（15 mol%）为绿色催化剂，开发了一种简单、方便、环保的一锅法合成1,2,4-三唑烷-3-硫酮的绿色催化剂。各种取代的醛或酮与氨基硫脲反应良好，可得到非常大量的所需化合物。所开发的协议具有几个优点，例如反应时间更短、反应条件温和、易于处理、纯化程序简单、水作为溶剂以及宽底物范围耐受性。此外，在不影响最终产品收率的情况下，催化剂被循环使用（最多 4 个循环）。 图形概要 目前的协议演示了在水性条件下从各种取代的醛或酮与氨基硫脲合成 1,2,4-triazolidine-3-硫酮。在催化量的葡甲胺存在下，在室温下简单地搅拌反应，很快得到所需产物的极好产率。该方法操作简单，环保。
• Tartaric Acid as an Expeditious and Green Catalyst for the Synthesis of 1,2,4-Triazolidine-3-thiones in an Aqueous Medium
  作者：Simren S. Salim、Liklesha B. Masram、Yatin U. Gadkari、Angad B. Barkule、Vikas N. Telvekar

  DOI：10.1080/00304948.2023.2202107

  日期：2023.11.2

  Published in Organic Preparations and Procedures International: The New Journal for Organic Synthesis (Vol. 55, No. 6, 2023)

  发表于《国际有机制备和程序：有机合成新杂志》（第 55 卷，第 6 期，2023 年）