2-(naphthalen-2-yl)indolizine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(naphthalen-2-yl)indolizine
• 英文别名: 2-Naphthalen-2-ylindolizine
• 化学式: C₁₈H₁₃N
• 分子量: 243.308
• InChiKey: JAUGSCVEFZGDER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 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：
  4.4
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(naphthalen-2-yl)indolizine 、 4-甲苯硫酚 在 碘化铵 、 氧气 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以78%的产率得到2-(naphthalen-2-yl)-1,3-bis(p-tolylthio)indolizine
  参考文献：
  名称：

  NH4I-catalyzed C–S bond formation via an oxidation relay strategy: Efficient access to dithioether decorated indolizines

  摘要：

  An efficient NH4I-catalyzed C-H/S-H cross-coupling reaction of indolizines with thiols is reported. Compared to previous methods, this environmentally friendly oxidation relay strategy uses O-2 as an oxidant to afford dithioether decorated indolizines in up to 98% yield. Promising results have been obtained, indicating the high applicability and atom economy of this method. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2020.152368
• 作为产物：
  描述：

  2-萘乙酮 在 对甲苯磺酸 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 34.17h， 生成 2-(naphthalen-2-yl)indolizine
  参考文献：
  名称：

  Oxidation Potential-Guided Electrochemical Radical–Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines

  摘要：

  DOI：

  10.1021/acs.joc.1c00873

文献信息

• Transition-Metal-Free Regioselective Cross-Coupling: Controlled Synthesis of Mono- or Dithiolation Indolizines
  作者：Bin Li、Zhiyu Chen、Hua Cao、Hong Zhao

  DOI：10.1021/acs.orglett.8b01168

  日期：2018.6.1

  indolizines with thiols has been developed for the first time to describe a workable route to indolizine thioethers. This finding provides a new method and more straightforward pathway for controllable synthesis of mono- or dithiolation indolizines that are otherwise difficult to obtain by the literature methods. The reaction exhibits good functional group tolerance and high efficiency and affords the products

  首次开发了一种有效的无过渡金属的吲哚嗪与硫醇的区域选择性C–H / S–H交叉偶联，以描述制备吲哚嗪硫醚的可行途径。这一发现为可控合成单硫醇或二硫醇化的吲哚嗪提供了新的方法和更直接的途径，否则文献方法很难获得。该反应表现出良好的官能团耐受性和高效率，并提供了良好至优异收率的产物。
• Mechanochemical Synthesis of 1,2-Diketoindolizine Derivatives from Indolizines and Epoxides Using Piezoelectric Materials
  作者：Yumei Wang、Ziwu Zhang、Lichan Deng、Tianfeng Lao、Zhengquan Su、Yue Yu、Hua Cao

  DOI：10.1021/acs.orglett.1c02575

  日期：2021.9.17

  A simple and efficient mechanochemical-induced approach for the synthesis of 1,2-diketoindolizine derivatives has been developed. BaTiO3 was used as the piezoelectric material in this transformation. This method features no usage of solvent, simple experimental operation, scalable potential, and high conversion efficiency, which make it attractive and practical.

  已经开发了一种简单有效的机械化学诱导方法来合成 1,2-二酮吲哚嗪衍生物。BaTiO 3用作该转变中的压电材料。该方法不使用溶剂，实验操作简单，潜力可扩展，转化效率高，具有吸引力和实用性。
• Synthesis of Pyrrolo[2,1,5-<i>cd</i>]indolizine Rings via Visible-Light-Induced Intermolecular [3+2] Cycloaddition of Indolizines and Alkynes
  作者：Yu Zhang、Yue Yu、Bing-bing Liang、Yong-yan Pei、Xiang Liu、Hua-gang Yao、Hua Cao

  DOI：10.1021/acs.joc.0c01253

  日期：2020.8.21

  smoothly underwent visible-light-induced intermolecular [3+2] annulations with internal alkynes to afford pyrrolo[2,1,5-cd]indolizine in good to excellent yields with high regioselectivity. Through this cascade reaction, a series of fluoroactive fused indolizines with a large π-system were conveniently synthesized. The usage of visible light as energy source with air as a stoichiometric oxidant under

  一系列吲哚并嗪通过内部炔烃顺利地进行了可见光诱导的分子间[3 + 2]环空拆分，从而以良好的产率和良好的区域选择性提供了吡咯并[2,1,5- cd ]吲哚并嗪。通过该级联反应，方便地合成了具有大π系统的一系列含氟稠合吲哚嗪。在简单条件下使用可见光作为能源，以空气作为化学计量的氧化剂，使该过程具有吸引力和实用性。
• Organocatalytic C3-functionalization of indolizines: synthesis of biologically important indolizine derivatives
  作者：Yi-Zhu Zhang、Feng-Tao Sheng、Zuoquan Zhu、Zhi-Ming Li、Shu Zhang、Wei Tan、Feng Shi

  DOI：10.1039/d0ob01230k

  日期：——

  Brønsted acid-catalyzed C3-alkylation of indolizines has a wide applicability, which can serve as a useful method for synthesizing C3-functionalized indolizine derivatives with structural diversity. This reaction has fulfilled the task of developing organocatalytic C3-functionalization of indolizines for the synthesis of biologically important indolizine derivatives.

  Brønsted 酸催化的中氮茚的 C3 烷基化已经建立，其中包括不同的亲电子试剂，例如邻羟基苄醇、对醌甲基化物和邻醌甲基化物的其他前体，以及2-吲哚甲醇。通过使用这种方法，以总体良好的收率（高达 89%）合成了一系列 C3 功能化的中氮茚。这些实施例表明，Brønsted 酸催化的 C3 烷基化中氮茚具有广泛的适用性，可作为合成具有结构多样性的 C3 官能化中氮茚衍生物的有用方法。该反应完成了开发中氮茚的有机催化 C3 官能化以合成具有生物学重要意义的中氮茚衍生物的任务。
• Photoinduced successive oxidative ring-opening and borylation of indolizines with NHC–boranes
  作者：Huitao Zheng、Honggang Xiong、Chaobo Su、Hua Cao、Huagang Yao、Xiang Liu

  DOI：10.1039/d1ra08072e

  日期：——

  A facile photoinduced successive oxidative ring-opening and borylation of indolizines with NHC–boranes via a one-pot method has been unveiled. This photo-promoted strategy enables the formation of unsaturated NHC–boryl carboxylates under transition metal-free and radical initiator-free conditions. A wide array of pyridine-containing NHC–boryl carboxylates were directly prepared in moderate to good

  已经揭示了通过一锅法用 NHC-硼烷轻松光诱导中氮茚的连续氧化开环和硼化。这种光促进策略能够在无过渡金属和无自由基引发剂的条件下形成不饱和的 NHC-硼基羧酸盐。以中等至良好的产率直接制备了多种含吡啶的 NHC-硼基羧酸盐。这项工作有助于更好地了解中氮茚和 NHC-硼烷的反应性和光行为。