7-chloro-2-phenylbenzo[d]thiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 7-chloro-2-phenylbenzo[d]thiazole
• 英文别名: 7-chloro-2-phenylbenzothiazole；7-Chloro-2-phenyl-1,3-benzothiazole
• 化学式: C₁₃H₈ClNS
• 分子量: 245.732
• InChiKey: VMZHCIMYHJIMEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(2,3-Dichloro-phenyl)-thiobenzamide 反应 72.0h， 生成 7-chloro-2-phenylbenzo[d]thiazole
  参考文献：
  名称：

  Photochemical Synthesis of s-Triazolo[3,4-b]benzothiazole and Mechanistic Studies on Benzothiazole Formation

  摘要：

  A general photochemical synthesis of s-triazolo[3,4-b]benzothiazoles from 4,5-disubstituted 1,2,4-triazole-3-thione is described. Steady photolysis, quantum yield determination, and laser flash photolysis experiments have been carried out. An intramolecular electron transfer mechanism has been proposed.

  DOI：

  10.1021/jo962190v

文献信息

• One-pot copper-catalyzed synthesis of 2-substituted benzothiazoles from 2-iodoanilines, benzyl chlorides and elemental sulfur
  作者：Zhao Yang、Renhe Hu、Xiaotong Li、Xin Wang、Ren Gu、Shiqing Han

  DOI：10.1016/j.tetlet.2017.05.004

  日期：2017.6

  An efficient one-pot three-component reaction of 2-iodoanilines, benzyl chlorides and elemental sulfur to form 2-substituted benzothiazoles in satisfactory yields (up to 98%) has been described. The reaction tolerated a wide range of functional groups on the aromatic ring. And heterocycle methylene chlorides substrates were also found to be compatible.

  已经描述了2-碘苯胺，苄基氯和元素硫的有效的一锅三组分反应以令人满意的产率（高达98％）形成2-取代的苯并噻唑。该反应容许芳环上的多种官能团。并且还发现杂环二氯甲烷底物是相容的。
• Riboflavin as Photoredox Catalyst in the Cyclization of Thiobenzanilides: Synthesis of 2-Substituted Benzothiazoles
  作者：Lydia M. Bouchet、Adrián A. Heredia、Juan E. Argüello、Luciana C. Schmidt

  DOI：10.1021/acs.orglett.9b04384

  日期：2020.1.17

  Benzothiazoles are synthesized from thiobenzanilides using riboflavin as a photosensitizer and potassium peroxydisulfate as a sacrificial oxidizing agent under visible light irradiation. The methodology accepts a broad range of functional groups and affords the 2-substituted benzothiazoles by transition-metal-free organic photoredox catalysis under very mild conditions.

  在可见光照射下，使用核黄素作为光敏剂，过氧二硫酸钾作为牺牲氧化剂，由硫代苯甲酰肼合成苯并噻唑。该方法学接受广泛的官能团，并在非常温和的条件下通过无过渡金属的有机光氧化还原催化作用而提供了2-取代的苯并噻唑。
• Copper‐Catalyzed Aerobic Oxidation of Amines to Benzothiazoles via Cross Coupling of Amines and Arene Thiolation Sequence
  作者：Jihyeon Kim、Kyungsoo Oh

  DOI：10.1002/adsc.202000598

  日期：2020.9.8

  A one‐pot three‐component synthesis of benzothiazoles has been developed using the copper‐catalyzed aerobic cross coupling of amines followed by arene thiolation using elemental sulfur. The dual roles of elemental sulfur and CuCl(OH)‐TMEDA in the aerobic amine oxidation and the aniline thiolation enable the facile access to benzothiazole derivatives from readily available starting materials. The operational

  通过铜催化的胺的需氧交叉偶联，然后使用元素硫进行的芳烃硫醇化，已经开发出了一种单锅三组分苯并噻唑的合成方法。元素硫和CuCl（OH）-TMEDA在好氧胺氧化和苯胺硫醇化中的双重作用使得可以轻松地从容易获得的起始原料中获得苯并噻唑衍生物。当前混杂催化剂体系的操作简单性表明在制备杂环化合物中具有很高的合成潜力。
• Elemental Sulfur Disproportionation in the Redox Condensation Reaction between<i>o</i>-Halonitrobenzenes and Benzylamines
  作者：Thanh Binh Nguyen、Ludmila Ermolenko、Pascal Retailleau、Ali Al-Mourabit

  DOI：10.1002/anie.201408397

  日期：2014.12.8

  The disproportionation of elemental sulfur at moderate temperatures is investigated in the redox condensation involving o‐halonitrobenzenes 1 and benzylamines 2. As a redox moderator, elemental sulfur plays the dual role of both electron donor and acceptor, generating its lowest and highest oxidation states: S−2 (sulfide equivalent) in benzothiazole 3 and S+6 (sulfate equivalent) in sulfamate 4, and

  在涉及邻卤代硝基苯1和苄胺2的氧化还原缩合反应中，研究了元素硫在中等温度下的歧化作用。作为氧化还原缓和剂，元素硫同时发挥电子给体和受体的双重作用，产生最低和最高的氧化态：苯并噻唑3中的S -2（硫化物当量）和氨基磺酸盐4中的S +6（硫酸当量），并填充整体氧化还原凝聚过程的电子间隙。伴随着这个过程，一系列的反应还原了1的硝基，还原了2的氨甲基，无金属的芳族卤素取代和缩合最终形成了2-芳基苯并噻唑3。
• A simple approach to benzothiazoles from 2-chloronitrobenzene, elemental sulfur, and aliphatic amine under solvent-free and catalyst-free conditions
  作者：Yao Tong、Qiang Pan、Zengqiang Jiang、Dazhuang Miao、Xuesong Shi、Shiqing Han

  DOI：10.1016/j.tetlet.2014.08.037

  日期：2014.10

  A novel solvent-free and catalyst-free synthesis of benzothiazoles from 2-chloronitrobenzene, elemental sulfur, and aliphatic amine has been developed. The reaction tolerated a wide range of functionalities, and various benzothiazoles were synthesized in moderate to good yields in the absence of external oxidant or reductant. (C) 2014 Elsevier Ltd. All rights reserved.