5-methoxy-2-(thiophen-2-yl)-1H-indole-3-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-methoxy-2-(thiophen-2-yl)-1H-indole-3-carbonitrile
• 英文别名: 5-methoxy-2-thiophen-2-yl-1H-indole-3-carbonitrile
• 化学式: C₁₄H₁₀N₂OS
• 分子量: 254.312
• InChiKey: DDJANIKKYHKJFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-thiophenedithiocarboxylic acid 在 copper(l) iodide 、 sodium hydride 、 L-脯氨酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-methoxy-2-(thiophen-2-yl)-1H-indole-3-carbonitrile
  参考文献：
  名称：

  Synthesis of N-Functionalized/NH-Multisubstituted Indoles, Thienopyrroles, Pyrroloindoles, and Pyrazolopyrroles via Sequential One-Pot Base-Mediated and Copper-Catalyzed Inter- and Intramolecular Amination of 2-[2-Bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitriles

  摘要：

  A novel, efficient route to substituted 1-N-(het)aryl/NH-2-(het)aryl-3-cyanoindoles and related pyrrolo-fused heterocycles such as thienopyrroles, pyrroloindoles, and pyrazolopyrroles has been reported. The overall protocol involves sequential cycloamination of readily available 2-[2-bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitrile precursors with primary amines or amides via two key C-N bond-forming processes, one base-mediated intermolecular and the other Cu-catalyzed intramolecular arylamination leading to N(1)-C(2) and N(1)-C(7a) bond formation, respectively, in a two-step one-pot procedure.

  DOI：

  10.1021/jo501114a

文献信息

• Amine Directed Pd(II)-Catalyzed C–H Activation-Intramolecular Amination of <i>N</i>-Het(aryl)/Acyl Enaminonitriles and Enaminones: An Approach towards Multisubstituted Indoles and Heterofused Pyrroles
  作者：Somaraju Yugandar、Saidulu Konda、Hiriyakkanavar Ila

  DOI：10.1021/acs.joc.5b02902

  日期：2016.3.4

  of either palladium acetate/cupric acetate catalytic system under oxygen atmosphere or palladium acetate/silver carbonate in the presence of pivalic acid as additive. The method is compatible with a diverse range of substituents on the aryl ring as well as at the 2- and 3-positions of the indole ring. The versatility of this method was further demonstrated by elaborating it for the synthesis of heterofused

  通过分子内氧化C–H活化胺化现有的2-（杂）芳基-3-（杂）芳基/烷基-3-（杂）芳基/酰基氨基丙烯腈/烯胺酮前体，开发了一种多取代吲哚的有效途径。在氧气气氛下存在乙酸钯/乙酸铜催化体系，或在新戊酸作为添加剂的情况下存在乙酸钯/碳酸银。该方法与芳基环以及吲哚环的2-和3-位上的各种取代基兼容。详细说明了该方法的多功能性，可用于合成杂稠稠合的吡咯，如噻吩并[2,3- b ]吡咯，噻吩并[3,2- b ]吡咯，吡咯并[2,3- b ]吲哚和pyrrolo [2,3-b ]吡啶，收率高。已经提出了形成这些吲哚的可能机理。
• Synthesis of N-Functionalized/NH-Multisubstituted Indoles, Thienopyrroles, Pyrroloindoles, and Pyrazolopyrroles via Sequential One-Pot Base-Mediated and Copper-Catalyzed Inter- and Intramolecular Amination of 2-[2-Bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitriles
  作者：S. Vijay Kumar、B. Saraiah、G. Parameshwarappa、H. Ila、Girijesh K. Verma

  DOI：10.1021/jo501114a

  日期：2014.9.5

  A novel, efficient route to substituted 1-N-(het)aryl/NH-2-(het)aryl-3-cyanoindoles and related pyrrolo-fused heterocycles such as thienopyrroles, pyrroloindoles, and pyrazolopyrroles has been reported. The overall protocol involves sequential cycloamination of readily available 2-[2-bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitrile precursors with primary amines or amides via two key C-N bond-forming processes, one base-mediated intermolecular and the other Cu-catalyzed intramolecular arylamination leading to N(1)-C(2) and N(1)-C(7a) bond formation, respectively, in a two-step one-pot procedure.