3,5-bis(3-bromophenyl)-1,2,4-thiadiazole

• 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: 3,5-bis(3-bromophenyl)-1,2,4-thiadiazole
• 化学式: C₁₄H₈Br₂N₂S
• 分子量: 396.105
• InChiKey: YBTWNEJNSBOKLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴硫代苯甲酰胺 在 氧气 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 8.0h， 以64%的产率得到3,5-bis(3-bromophenyl)-1,2,4-thiadiazole
  参考文献：
  名称：

  好氧可见光诱导分子间 S-N 键构建：在无光敏剂条件下由硫代酰胺合成 1,2,4-噻二唑

  摘要：

  在无光敏剂的条件下，通过可见光诱导硫代酰胺的氧化环化，开发了一种伴随合成 1,2,4-噻二唑的 S-N 构建的绿色方法。

  DOI：

  10.1002/ejoc.202100440

文献信息

• An Unexpected Result of the Reaction of Benzothioamide Derivatives with 2-Aryl-2-bromoacetonitriles
  作者：Hassan Zali Boeini、Mehdi Mobin

  DOI：10.1002/hlca.201100110

  日期：2011.11

  Unexpectedly, in the reaction of 2‐bromo‐2‐phenylacetonitrile derivatives with 2 mol‐equiv. of benzothioamide in DMSO, 3,5‐diaryl‐1,2,4‐thiadiazoles were obtained in excellent yields (83–90%) and in short reaction times (5–10 min). It is found that, in DMF, a quite different reaction takes place and 2,5‐diaryl‐1,3‐thiazol‐4‐amines are formed as the main products.

  出乎意料的是，在2-溴-2-苯基乙腈衍生物与2摩尔当量的反应中。DMSO中的苯甲硫酰胺可得到3,5-二芳基-1,2,4-噻二唑，收率极高（83-90％），反应时间短（5-10分钟）。发现在DMF中发生了完全不同的反应，并且形成了2,5-二芳基-1,3-噻唑-4-胺作为主要产物。
• TCT-DMSO/[bmim]BF4: A novel promoter system for the synthesis of 3,5-diaryl-1,2,4-thiadiazoles at ambient temperature
  作者：Ahmad R. Khosropour、Jalil Noei

  DOI：10.1002/jhet.261

  日期：2011.1

  efficient and practical procedure for direct synthesis of 3,5‐diaryl‐1,2,4‐thiadiazoles by thioamides with 2,4,6‐trichloro‐1,3,5‐triazine (TCT) and dimethylsulfoxide using 1‐butyl‐3‐methylimidazolium tetrafluoroborate as an eco‐friendly reaction medium under ambient temperature is described. This protocol can be considered as a new procedure for 3,5‐diaryl‐1,2,4‐thiadiazoles synthesis. J. Heterocyclic Chem

  一种高效实用的程序，可使用1-丁基-硫代酰胺与2,4,6-三氯-1,3,5-三嗪（TCT）和二甲亚砜通过硫酰胺直接合成3,5-二芳基-1,2,4-噻二唑描述了在环境温度下作为环境友好反应介质的3-甲基咪唑鎓四氟硼酸盐。该方案可以看作是合成3,5-二芳基-1,2,4-噻二唑的新方法。J.杂环化​​学。（2010）。
• Visible-light promoted serendipitous synthesis of 3,5-diaryl-1,2,4-thiadiazoles <i>via</i> oxidative dimerization of thiobenzamides
  作者：Ranjana Aggarwal、Mona Hooda

  DOI：10.1080/17415993.2021.2005064

  日期：2022.5.4

  In the present manuscript, we report serendipitous synthesis of 3,5-diaryl-1,2,4-thiadiazoles with the aid of a household compact fluorescent lamp (CFL). In presence of α-bromo-β-diketone, thiobenzamides undergo oxidative dimerization to generate corresponding 3,5-diaryl-1,2,4-thiadiazoles in excellent yields in just 5 min instead of expected 2-aryl-4-methyl-5-acylthiazoles. Inhibition of the reaction

  在本手稿中，我们报告了在家用紧凑型荧光灯 (CFL) 的帮助下偶然合成 3,5-二芳基-1,2,4-噻二唑。在 α-溴-β-二酮存在下，硫代苯甲酰胺经过氧化二聚化，在 5 分钟内以优异的产率生成相应的 3,5-二芳基-1,2,4-噻二唑，而不是预期的 2-aryl-4-methyl-5 -酰基噻唑。自由基清除剂 (2,2,6,6-四甲基哌啶-1-基)氧基 (TEMPO) 对反应的抑制表明二聚化是通过自由基过程发生的。所开发方案的合成价值是通过在更短的时间内合成超过 11 种不同的 1,2,4-噻二唑，在环境良性无添加剂条件下具有极高的纯度和简单的后处理程序。
• A chromatography-free one-pot, two-step synthesis of 1,2,4-thiadiazoles from primary amides via thiolation and oxidative dimerization under solvent-free conditions: a greener approach
  作者：Khushbu Rajput、Vishal Singh、Sundaram Singh、Vandana Srivastava

  DOI：10.1039/d4ra03993a

  日期：——

  An efficient and practical one-pot, two-step synthesis of 1,2,4-thiadiazoles from primary amides with Lawesson reagent (LR) and tert-butyl hydrogen peroxide (TBHP) without solvent is demonstrated for the first time. This groundbreaking and environmentally friendly approach utilises readily available starting materials and eliminates the use of traditional solvents in the reaction process. The broad

  首次证明了在无溶剂的情况下，用劳森试剂（LR）和叔丁基过氧化氢（TBHP）从伯酰胺高效实用的一锅两步合成1,2,4-噻二唑。这种突破性且环保的方法利用了现成的原材料，并消除了反应过程中传统溶剂的使用。广泛的底物范围、在温和和无金属条件下出色的官能团耐受性、快速转化和出色的产率是该方法的基本特征。所有化合物均无需柱色谱法纯化。
• Optimizing thiadiazole analogues of resveratrol versus three chemopreventive targets
  作者：Abdelrahman S. Mayhoub、Laura Marler、Tamara P. Kondratyuk、Eun-Jung Park、John M. Pezzuto、Mark Cushman

  DOI：10.1016/j.bmc.2011.09.031

  日期：2012.1

  Chemoprevention is an approach to decrease cancer morbidity and mortality through inhibition of carcinogenesis and prevention of disease progression. Although the trans stilbene derivative resveratrol has chemopreventive properties, its action is compromised by weak non-specific effects on many biological targets. Replacement of the stilbene ethylenic bridge of resveratrol with a 1,2,4-thiadiazole heterocycle and modification of the substituents on the two aromatic rings afforded potential chemopreventive agents with enhanced potencies and selectivities when evaluated as inhibitors of aromatase and NF-kappa B and inducers of quinone reductase 1 (QR1). (C) 2011 Elsevier Ltd. All rights reserved.