2-thiophen-2-yl-benzo[d]imidazo[2,1-b]thiazole | 38956-30-8

• 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: 2-thiophen-2-yl-benzo[d]imidazo[2,1-b]thiazole
• 英文别名: benzo[d]imidazo[2,1-b]thiazole；2-(2-Thienyl)imidazo[2,1-b][1,3]benzothiazole；2-thiophen-2-ylimidazo[2,1-b][1,3]benzothiazole
• CAS: 38956-30-8
• 化学式: C₁₃H₈N₂S₂
• 分子量: 256.352
• InChiKey: UIAWUVKZYJYKNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-thiophen-2-yl-benzo[d]imidazo[2,1-b]thiazole 、 溴氟甲基膦酸二乙酯 在 rose bengal 、 碳酸氢钠 、 联硼酸频那醇酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以78%的产率得到diethyl (difluoro(2-(thiophen-2-yl)benzo[d]imidazo[2,1-b]thiazol-3-yl)methyl)phosphonate
  参考文献：
  名称：

  Organophotoredox-Catalyzed C(sp²)–H Difluoromethylenephosphonation of Imidazoheterocycles

  摘要：

  A mild and efficient method for the direct difluoromethylenephosphonation of imidazopyridines has been developed using rose bengal (RB) as a photoredox catalyst. Bis(pinacolato)diboron (B(2)pin(2)) is found to be a crucial additive in the present reaction. The present methodology is also applicable to other heterocycles like imidazo[2,1-b]thiazole, benzo[d]imidazo-[2,1-b]thiazole, and indole. The reaction possibly proceeds through a single electron transfer (SET) process.

  DOI：

  10.1021/acs.orglett.9b01954
• 作为产物：
  描述：

  2-(2-imino-benzothiazol-3-yl)-1-thiophen-2-yl-ethanone 在 盐酸 作用下， 反应 4.0h， 生成 2-thiophen-2-yl-benzo[d]imidazo[2,1-b]thiazole
  参考文献：
  名称：

  Investigations in the imidazole series

  摘要：

  DOI：

  10.1007/bf00944233

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。
• Visible light-induced photocatalytic C–H ethoxycarbonylmethylation of imidazoheterocycles with ethyl diazoacetate
  作者：Suvam Bhattacharjee、Sudip Laru、Sadhanendu Samanta、Mukta Singsardar、Alakananda Hajra

  DOI：10.1039/d0ra05795a

  日期：——

  A visible light-mediated regioselective C3-ethoxycarbonylmethylation of imidazopyridines with ethyl diazoacetate (EDA) was achieved under mild reaction conditions. In contrast to the carbene precursors from α-diazoester a first C3-ethoxycarbonylmethylation of imidazopyridines via a radical intermediate has been established. The present methodology provides a concise route to access pharmacologically

  在温和的反应条件下，用重氮乙酸乙酯 (EDA) 实现了咪唑并吡啶的可见光介导的区域选择性 C3-乙氧基羰基甲基化。与来自 α-重氮酯的卡宾前体相比，已经建立了咪唑并吡啶通过自由基中间体的第一次 C3-乙氧基羰基甲基化。本方法提供了一种以高产率获得具有广泛官能团耐受性的药理学有用酯的简明途径。
• Electrochemical oxidative C–H/N–H cross-coupling for C–N bond formation with hydrogen evolution
  作者：Yi Yu、Yong Yuan、Huilin Liu、Min He、Mingzhu Yang、Pan Liu、Banying Yu、Xuanchi Dong、Aiwen Lei

  DOI：10.1039/c8cc09899a

  日期：——

  catalyst-free and exogenous-oxidant-free conditions, a series of C-3 aminated imidazo[1,2-a]pyridines were synthesized by electrochemical intermolecular oxidative C–H/N–H cross-coupling. Furthermore, by using a catalytic amount of ferrocene as the mediator, electrochemical intramolecular oxidative C–H/N–H cross-coupling for the synthesis of 10H-benzo[4,5]imidazo[1,2-a]indole derivatives has also been accomplished

  在无金属催化剂和无外源氧化剂的条件下，通过电化学分子间氧化C–H / N–H交叉偶联反应，合成了一系列C-3胺化的咪唑并[1,2- a ]吡啶。此外，通过使用催化量的二茂铁作为介体，用于合成10 H-苯并[4,5]咪唑并[1,2- a ]吲哚衍生物的电化学分子内氧化C–H / N–H交叉偶联具有也完成了。
• Aminomethylation of Imidazoheterocycles with Morpholine
  作者：Susmita Mondal、Sadhanendu Samanta、Mukta Singsardar、Alakananda Hajra

  DOI：10.1021/acs.orglett.7b01594

  日期：2017.7.21

  hitherto unreported aminomethylation occurs at C-3 of imidazopyridines with morpholine in the presence of (diacetoxyiodo)benzene at ambient temperature in short reaction times. This methodology is also applicable to indolizine, imidazo[2,1-b]thiazole, benzo[d]imidazo[2,1-b]thiazole, and indole. Interestingly, the aminomethylation involving morpholine as a source of methylene group is a new phenomenon. This

  在（二乙酰氧基碘）苯的存在下，在环境温度下以短的反应时间，在吗啉对咪唑并吡啶的C-3处发生了迄今未报道的氨基甲基化。该方法也适用于吲哚嗪，咪唑并[2,1- b ]噻唑，苯并[ d ]咪唑并[2,1- b ]噻唑和吲哚。有趣的是，涉及吗啉作为亚甲基来源的氨基甲基化是一种新现象。该方案对于在温和的反应条件下合成氨基甲基化衍生物具有很大的潜力。
• 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。