5-(p-tolylthio)-3-methyl-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)-3-methyl-6-phenylimidazo[2,1-b]thiazole
• 英文别名: 3-methyl-6-phenyl-5-(p-tolylthio)imidazo[2, 1-b]thiazole；3-Methyl-5-(4-methylphenyl)sulfanyl-6-phenylimidazo[2,1-b][1,3]thiazole
• 化学式: C₁₉H₁₆N₂S₂
• 分子量: 336.481
• InChiKey: JAODCGFWBZIWLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  3-甲基-6-苯基-咪唑并[2,1-b]噻唑 、 4-甲基苯硫代磺酸 S-(4-甲基苯基)酯 以 水 为溶剂， 反应 0.33h， 以88%的产率得到5-(p-tolylthio)-3-methyl-6-phenylimidazo[2,1-b]thiazole
  参考文献：
  名称：

  咪唑并[2,1-b]噻唑与磺酰肼在水中的微波辅助和无催化剂磺酰化

  摘要：

  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

  DOI：

  10.1080/10426507.2020.1768537

文献信息

• 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。
• Copper-catalyzed thiolation of imidazo[1,2-a]pyridines with (hetero)aryl thiols using molecular oxygen
  作者：Zhishuo Zheng、Deyu Qi、Lei Shi

  DOI：10.1016/j.catcom.2015.03.023

  日期：2015.6

  A new and facile copper-catalyzed thiolation of imidazo[1,2-a]pyridines with (hetero)aryl thiols was developed for the formation of C-S bond by using molecular oxygen as oxidant under base-free conditions. The presented protocol has provided the selective C-3 sulfenated products with good yield. A computational study was carried out by using the B3LYP density functional theory to elucidate the regioselectivity of C-2 and C-3. Calculation results indicated that the thiolation toward C-3 was easier and smoother, which was consistent with our experiment results. (C) 2015 Elsevier B.V. All rights reserved.