1,2,3,4-tetrahydrobenzo[d]benzo[4,5]imidazo[2,1-b]thiazole | 23019-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1,2,3,4-tetrahydrobenzo[d]benzo[4,5]imidazo[2,1-b]thiazole
• 英文别名: 1,2,3,4-tetrahydro-benzo[d]benzo[4,5]imidazo[2,1-b]thiazole；3,4-Tetrahydrobenzimidazo[2,1-b]benzothiazole；1,2,3,4-tetrahydrobenzimidazolo[2,1-b][1,3]benzothiazole
• CAS: 23019-27-4
• 化学式: C₁₃H₁₂N₂S
• 分子量: 228.318
• InChiKey: KHAGCXRODQMMKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯环己酮 在 乙酸酐 作用下， 生成 1,2,3,4-tetrahydrobenzo[d]benzo[4,5]imidazo[2,1-b]thiazole
  参考文献：
  名称：

  Singh,H.; Singh,S., Indian Journal of Chemistry, 1973, vol. 11, p. 311 - 312

  摘要：

  DOI：

文献信息

• Metal‐Free Synthesis of Imidazo[2,1‐ <i>b</i> ]thiazoles from Thioimidazoles and Ketones Mediated by Selectfluor
  作者：Jinwu Zhao、Qiannan Xiao、Jiaxi Chen、Jingxiu Xu

  DOI：10.1002/ejoc.202000815

  日期：2020.8.31

  Promoted by Selectfluor, imidazo[2,1‐b]thiazoles could be prepared from thioimidazoles and ketones. This metal‐free protocol was applicable to various ketones, including strong electron‐withdrawing substituted aryl ketones and alkyl ketones. Moreover, this procedure featured simple operation and easy work‐up.

  在Selectfluor的促进下，可以从硫代咪唑和酮制备咪唑并[2,1- b ]噻唑。该无金属方案适用于各种酮，包括强吸电子取代的芳基酮和烷基酮。此外，该程序具有操作简单，易于维护的特点。
• DMSO/H ₂ O ₂ Promoted Regioselective Synthesis of Benzoimidazo[2,1‐b]thiazoles from 2‐Mercaptobenzimidazoles and Ketones in Water
  作者：Jingxiu Xu、Renjin Deng、Jiaxi Chen、Xiaodong Tang、Jinwu Zhao

  DOI：10.1002/adsc.201900909

  日期：2019.11.19

  We report a green and regioselective process for the construction of benzoimidazo[2,1‐b]thiazole skeletons in water using DMSO/H2O2 as an oxidant. The experimental data lend support to a mechanism in which the transformation is initiated by oxidizing methylene of ketone into carbon radical under the oxidation of DMSO/H2O2. This operationally simple and metal‐free procedure could facilitate a diverse

  我们报告了使用DMSO / H 2 O 2作为氧化剂在水中构建苯并咪唑并[2,1-b]噻唑骨架的绿色和区域选择性过程。实验数据为通过在DMSO / H 2 O 2的氧化下将酮的亚甲基氧化为碳自由基而引发转化的机理提供了支持。这种操作简单且无金属的方法可以促进苯并咪唑并[2,1-b]噻唑衍生物的多样化收集。
• Photocatalytic aerobic α-thiolation/annulation of carbonyls with mercaptobenzimidazoles
  作者：Xiaochen Ji、Muyun Tan、Mei Fu、Guo-Jun Deng、Huawen Huang

  DOI：10.1039/c9ob00625g

  日期：——

  A concise aerobic photocatalysis using a blue LED combined with a Lewis acid has been developed to enable α-thiolation/annulation of carbonyls. Inexpensive, nontoxic Rose Bengal was demonstrated as the best catalyst. Hence, this transition-metal-free protocol allows mild Csp3–S couplings with both ketones and aliphatic aldehydes with a range of compatible useful functionalities.

  已经开发出一种使用蓝色LED与路易斯酸相结合的简洁的好氧光催化技术，以使α-硫醇化/羰基环化成为可能。廉价，无毒的玫瑰红被证明是最好的催化剂。因此，这种无过渡金属的方案允许温和的Csp 3 –S与酮和脂族醛同时偶联，并具有一系列兼容的有用功能。
• Synthesis of benzimidazo[2,1-b]benzothiazole derivatives through sequential Cu-catalyzed domino coupling and Pd-catalyzed Suzuki reaction
  作者：Jilong Gao、Jiaoyan Zhu、Lubin Chen、Yingying Shao、Jiaqi Zhu、Yijia Huang、Xiaoxia Wang、Xin Lv

  DOI：10.1016/j.tetlet.2014.04.070

  日期：2014.5

  the Cu-catalyzed domino coupling of o-dihaloarenes with 2-mercaptobenzimidazoles. The reaction is also applicable to a series of multi-functional substrates, affording the halo-containing products with excellent selectivity. The brominated products can further react with arylboronic acids under Pd catalysis to furnish the aryl-substituted benzimidazo[2,1-b]benzothiazole derivatives.

  通过邻二卤代芳烃与2-巯基苯并咪唑的铜催化多米诺偶联反应，可以高效，方便地合成各种苯并[ d ]苯并[4,5]咪唑并[ 2,1- b ]噻唑。该反应还适用于一系列多功能底物，从而提供具有优异选择性的含卤产物。溴化产物可以在Pd催化下进一步与芳基硼酸反应，得到芳基取代的苯并咪唑并[2,1- b ]苯并噻唑衍生物。
• A convenient one-pot synthesis of 2-benzimidazolyl-thioacetophenones and thiazolo[3,2-a]benzimidazoles
  作者：Abd El-Wareth A.O. Sarhan、Hasan A.H. El-Sherief、Abdalla M. Mahmoud

  DOI：10.1016/0040-4020(96)00569-8

  日期：1996.7

  etophenones 3a-d. Which on cyclization yield thiazolo[3,2-a]-benzimidazoles 4a-d. Acetylation of 3a,d gave the N-acetyl derivatives 5a,d. Cyclization of 3a-d or 5d in acetic anhydride or acetic anhydride / pyridine mixture afforded 6a-d. While reaction of 1 with aliphatic or alicyclic ketones gave directly 2,3-disubstituted thiazolo[3,2-a]benzimidazoles 7a-f and 8a-d respectively.

  2-巯基苯并咪唑（1）与芳族酮2a-d在酸化的乙酸中反应，得到2-苯并咪唑基硫代乙酰基苯乙酮3a-d。在环化反应中产生噻唑并[3，2-a]-苯并咪唑4a-d。3a，d的乙酰化得到N-乙酰基衍生物5a，d。3a-d或5d在乙酸酐或乙酸酐/吡啶混合物中的环化得到6a-d。当1与脂族或脂环族酮反应时，分别直接直接得到2，3-二取代的噻唑并[3，2-a]苯并咪唑7a-f和8a-d。