5-(p-tolylthio)-6-phenylimidazo[2,1-b]thiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(p-tolylthio)-6-phenylimidazo[2,1-b]thiazole
• 英文别名: 6-phenyl-5-(p-tolylthio)imidazo[2,1-b]thiazole；5-(4-methylphenyl)sulfanyl-6-phenylimidazo[2,1-b][1,3]thiazole
• 化学式: C₁₈H₁₄N₂S₂
• 分子量: 322.455
• InChiKey: PKJFISPEJIPHKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对甲苯磺酰氯 在 hydrazine hydrate 作用下， 以 neat (no solvent) 为溶剂， 反应 15.0h， 生成 5-(p-tolylthio)-6-phenylimidazo[2,1-b]thiazole
  参考文献：
  名称：

  磺酰肼诱导咪唑并杂芳烃的亚磺酰化：“无催化剂和无溶剂”方案

  摘要：

  摘要 已经开发了一种简单且无忧的咪唑杂环亚磺酰化可持续方案。磺酰肼已被用作原位活性硫代载体的生成剂，在纯条件下以“磺基硫酸盐”的形式以良好至优异的产率生产所需的亚磺酰化咪唑杂环化合物。新方法不需要任何溶剂或催化剂，只需调节反应物的比例即可。因此，该方法更环保且易于处理。

  DOI：

  10.1080/00397911.2022.2069506

文献信息

• Metal-free direct regioselective thiolation of imidazoheterocycles in water at room temperature
  作者：Dulin Kong、Qinghe Wang、Tiao Huang、Min Liang、Qiang Lin、Mingshu Wu

  DOI：10.1016/j.tet.2019.01.059

  日期：2019.3

  A metal-free direct thiolation of imidazoheterocycles with various thiophenol in water at room temperature has been developed. In addition, the chemistry provides several advantages including mild condition, high yields, good functional group tolerance, green solvents and suitable for large-scale operations.

  已开发出室温下在水中用各种硫酚对金属进行咪唑杂环的无金属直接硫醇化反应。此外，该化学方法还具有多种优势，包括条件温和，收率高，对官能团的耐受性好，绿色溶剂且适用于大规模操作。
• Iodine-catalyzed regioselective thiolation of imidazo[1,2-a]pyridines using sulfonyl hydrazides as a thiol surrogate
  作者：Avik Kumar Bagdi、Shubhanjan Mitra、Monoranjan Ghosh、Alakananda Hajra

  DOI：10.1039/c5ob00033e

  日期：——

  sulfenylation of imidazo[1,2-a]pyridines via C(sp(2))-H bond functionalization has been achieved using sulfonyl hydrazides as a thiol surrogate. A library of 3-sulfanylimidazopyridines with broad functionalities was synthesized under metal and oxidant-free practical reaction conditions. This methodology is also applicable for the regioselective sulfenylation of imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole

  碘催化的咪唑并[1,2-a]吡啶类通过C（sp（2））-H键功能化的区域选择性亚磺酰基已经使用磺酰肼作为硫醇替代物实现了。在没有金属和氧化剂的实际反应条件下，合成了具有广泛功能的3-磺酰胺基咪唑并吡啶类化合物的文库。该方法也适用于咪唑并[2,1-b]噻唑和苯并[d]咪唑并[2,1-b]噻唑的区域选择性亚磺酰基化。
• Microwave-assisted and catalyst-free sulfenylation of imidazo[2,1-<i>b</i>]thiazoles with sulfonyl hydrazides in water
  作者：Shaohua Wang、Run Luo、Lina Guo、Tianxi Zhu、Xu Chen、Wenjie Liu

  DOI：10.1080/10426507.2020.1768537

  日期：2020.10.2

  Abstract An efficient microwave-assisted and catalyst-free sulfenylation of imidazo[2,1-b]thiazoles with sulfonyl hydrazides has been developed in water. This method is practical and environmental friendly, and can be performed within a short reaction time. The sulfenylation reaction shows high regioselectivity, and excellent functional-group compatibility, giving the desired products in moderate to

  摘要 在水中开发了一种有效的微波辅助和无催化剂的咪唑并 [2,1-b] 噻唑与磺酰肼的磺酰化反应。该方法实用、环保，反应时间短。磺酰化反应显示出高区域选择性和优异的官能团兼容性，以中等至良好的产率得到所需的产物。图形摘要
• Iodine–triphenylphosphine mediated sulfenylation of imidazoheterocycles with sodium sulfinates
  作者：Xuhu Huang、Shucheng Wang、Bowen Li、Xin Wang、Zemei Ge、Runtao Li

  DOI：10.1039/c4ra17237j

  日期：——

  An efficient approach to sulfenyl imidazoheterocycles has been developed via iodine–triphenylphosphine mediated direct sulfenylation of imidazoheterocycles with sodium sulfinates. The reactions proceed smoothly under transition-metal-free conditions with a broad range of substrate scope, giving the desired products in moderate to excellent yields.

  通过碘-三苯基膦介导的亚磺酸钠直接作用于咪唑杂环的亚磺酰基化，已开发出一种有效的亚磺酰基咪唑杂环杂环的方法。反应在无过渡金属条件下进行，且底物范围宽广，可以以中等至极好的收率得到所需的产物。
• Visible-light-promoted sodium iodide-mediated sulfenylation of imidazo[1,2-a]pyridines heterocycle using thiosulfate as odorless electrophilic arylsulphenyl source
  作者：Zhen Xie、Mengxin Li、Molai Zhao、Xiaoqing Wen、Li Lin、Hezhong Jiang、Zongrui Hou、Jiahong Li

  DOI：10.1016/j.tetlet.2024.154915

  日期：2024.2

  iodide-mediated sulfuration reaction of imidazole heterocycles, prompted by visible light and using thiosulfate as an odorless electrophilic arylsulphenyl source, has been developed. Mechanistic investigations suggest that sodium iodide and thiol sulfonic ester produce a sulfur cationic intermediate upon light irradiation, which then participates in electrophilic substitution with an aromatic heterocycle. Exhibiting

  已经开发出一种碘化钠介导的咪唑杂环硫化反应，该反应由可见光引发并使用硫代硫酸盐作为无味亲电芳基硫苯基源。机理研究表明，碘化钠和硫醇磺酸酯在光照射下产生硫阳离子中间体，然后参与芳香杂环的亲电取代。该反应具有广泛的底物范围和对各种官能团的广泛耐受性，可提供中等至优异的产率。这为合成多种含硫化合物提供了一种有效的方法。