2-(3-Methoxy-phenyl)-benzo[d]imidazo[2,1-b]thiazole | 79889-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-Methoxy-phenyl)-benzo[d]imidazo[2,1-b]thiazole
• 英文别名: 2-(3-Methoxyphenyl)imidazo[2,1-b][1,3]benzothiazole
• CAS: 79889-64-8
• 化学式: C₁₆H₁₂N₂OS
• 分子量: 280.35
• InChiKey: FIPPJMMBPCSCOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-Methoxy-phenyl)-benzo[d]imidazo[2,1-b]thiazole 在 tert-butylammonium hexafluorophosphate(V) 作用下， 以 2,2,2-三氟乙醇 、 乙腈 为溶剂， 反应 4.5h， 以72%的产率得到2,2′-bis(3-methoxyphenyl)-3,3′-bibenzo[d]imidazo[2,1-b]thiazole
  参考文献：
  名称：

  咪唑并吡啶杂环与双杂芳基的电化学氧化均偶联反应

  摘要：

  已经开发了基于咪唑并吡啶的杂环的电化学脱氢均偶联反应，该反应提供了具有良好化学收率和高区域选择性的双杂芳基。该反应在室温下在简单的不分隔电池中进行，避免了使用任何金属催化剂，添加剂和氧化剂。该反应可耐受多种底物，为制备重要的生物活性双杂芳基化合物提供了简便而绿色的策略。

  DOI：

  10.1039/c7gc03563b
• 作为产物：
  描述：

  2-溴-3‘-甲氧基苯乙酮 以 乙二醇甲醚 、 丁酮 为溶剂， 反应 3.0h， 生成 2-(3-Methoxy-phenyl)-benzo[d]imidazo[2,1-b]thiazole
  参考文献：
  名称：

  Imidazo[2,1-b]benzothiazoles. 2. New immunosuppressive agents

  摘要：

  A series of 2-phenylimidazo[2,1-b]benzothiazole derivatives was prepared and tested for immunological activities. Some of the compounds showed significant suppressive activity of delayed type hypersensitivity (DTH) without inhibition of humoral immunity in mice by oral administration. The most active compound was 2-(m-hydroxyphenyl)imidazo[2,1-b]benzothiazole (20).

  DOI：

  10.1021/jm00153a014

文献信息

• Base-Promoted Transition-Metal-Free Arylation of Imidazo-Fused Heterocycles with Diaryliodonium Salts
  作者：Rahul Kumar、Chitrakar Ravi、Deepa Rawat、Subbarayappa Adimurthy

  DOI：10.1002/ejoc.201800286

  日期：2018.4.17

  The arylation of imidazo[1,2‐a]pyridine and benzo[d]imidazo[2,1‐b]thiazoles by using diaryliodonium salts has been developed. Potassium tert‐butoxide was used to promote this transition‐metal‐free reaction, which afforded the corresponding products in good to excellent yields.

  咪唑的芳基化[1,2一]吡啶和苯并[ d ]咪唑并[2,1- b ]通过使用二芳基碘盐已经开发噻唑。钾叔丁醇是用来促进此过渡金属无反应，得到相应的产品以良好至优异的产量。
• An Articulate Oxidative Transition-Metal-Free Homocoupling of Imidazo Heterocycles through C(sp² )-C(sp² ) Bond Formation
  作者：S. M. Abdul Shakoor、Sanjay K. Mandal、Rajeev Sakhuja

  DOI：10.1002/ejoc.201700238

  日期：2017.5.10

  A transition‐metal‐free oxidative approach for homocoupling of 2‐arylimidazo heterocycles by using a phenyliodine diacetate‐mediated protocol at ambient conditions has been demonstrated. The homocoupled products were also obtained in an organocatalytic fashion by using iodobenzene.

  已证明在环境条件下使用苯乙酸二乙酸苯酯介导的方案可实现2-芳基咪唑杂环的均相偶联的无过渡金属氧化方法。还通过使用碘苯以有机催化方式获得均偶联的产物。
• Synthesis of Bridgehead Nitrogen Heterocycles on a Solid Surface
  作者：Shashikanth Ponnala、S. T. V. S. Kiran Kumar、Bashir A. Bhat、Devi Prasad Sahu

  DOI：10.1081/scc-200051674

  日期：2005.4.1

  Abstract Bridgehead nitrogen heterocycles were synthesized from heteroaromatic amidines and cyclic or acyclic α‐bromoketones under solvent‐free conditions at room temperature on a solid surface in excellent yields, which are higher than those obtained with hitherto‐known methods of syntheses. #CDRI Communication No. 6545.

  摘要 桥头氮杂环是由杂芳脒和环状或非环状 α-溴酮在室温下无溶剂条件下在固体表面上以优异的收率合成的，收率高于迄今为止已知的合成方法。#CDRI 通讯第 6545 号。
• Synthesis of symmetrical methylene-bridged imidazoheterocycles using DMSO as methylene source under metal-free conditions
  作者：Ping Liu、Ziyan Shen、Yao Yuan、Peipei Sun

  DOI：10.1039/c6ob00977h

  日期：——

  Methylene-bridged imidazo-heterocycles were synthesized by a H₃PO₄-promoted bridging methylenation of imidazopyridines or similar heterocycles, in which DMSO was used as the carbon source.

  通过H₃PO₄促进的亚甲基化，合成了亚甲基桥联的咪唑杂环化合物，其中二甲基亚砜被用作碳源。
• Iron-catalyzed unprecedented formation of benzo[d]imidazo[2,1-b]thiazoles under solvent-free conditions
  作者：Sandip Gangadhar Balwe、Yeon Tae Jeong

  DOI：10.1039/c6ra24183b

  日期：——

  unprecedented formation of benzo[d]imidazo[2,1-b]thiazole during iron-catalyzed coupling of 2-aminobenzothiazole, aldehydes with nitroalkane in air has been observed. This unique transformation possibly occurs through a sequential aza-Henry reaction and subsequent intramolecular cyclization, followed by denitration. A variety of substituted benzo[d]imidazo[2,1-b]thiazole are obtained using this protocol

  观察到在空气中2-氨基苯并噻唑，醛与硝基烷的铁催化偶联过程中，苯并[ d ]咪唑并[ 2,1- b ]噻唑的空前形成。这种独特的转化可能是通过顺序的aza-Henry反应和随后的分子内环化，然后进行脱硝而发生的。使用该方案可获得各种取代的苯并[ d ]咪唑并[2,1- b ]噻唑。