4-(4-bromophenyl)-2H-pyrrolo[3,4-c]quinoline | 1419177-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(4-bromophenyl)-2H-pyrrolo[3,4-c]quinoline
• CAS: 1419177-22-2
• 化学式: C₁₇H₁₁BrN₂
• 分子量: 323.192
• InChiKey: HTESWDRYQCWMTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 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：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(4-bromophenyl)-2H-pyrrolo[3,4-c]quinoline 、 丙烯酸甲酯（MA） 在 palladium diacetate 、 三乙胺 作用下， 以 乙腈 为溶剂， 以52%的产率得到(E)-methyl 3-(4-(2H-pyrrolo[3,4-c]quinolin-4-yl)phenyl)acrylate
  参考文献：
  名称：

  One pot synthesis of pyrrolo[3,4-c]quinolinone/pyrrolo[3,4-c]quinoline derivatives from 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC)

  摘要：

  据报道，在碱性条件下，2-氨基芳基丙烯酸酯/2-氨基查耳酮与对甲苯基甲基异氰酸酯（TosMIC）通过一锅范柳森反应和环化反应，可获得 2H-吡咯并[3,4-c]喹啉-4(5H)-酮/2H-吡咯并[3,4-c]喹啉衍生物，这是一种高效实用的合成方法。所需的产品可以中等到良好的收率获得。

  DOI：

  10.1039/c4ob01580k
• 作为产物：
  描述：

  methyl (2-(4-(4-bromobenzoyl)-1H-pyrrol-3-yl)phenyl)carbamate 在 三氯氧磷 作用下， 以 乙腈 为溶剂， 以70%的产率得到4-(4-bromophenyl)-2H-pyrrolo[3,4-c]quinoline
  参考文献：
  名称：

  TFA-catalyzed C–N bond activation of enamides with indoles: efficient synthesis of 3,3-bisindolylpropanoates and other bisindolylalkanes

  摘要：

  An efficient TFA-catalyzed cleavage of C-N bonds in alkylation of indoles by tertiary enamides was described. A variety of bisindolylalkane derivatives, especially 3,3-bisindolylpropanoates, were expeditiously synthesized in good yields. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.098

文献信息

• Synthesis of 2H-pyrrolo[3,4-C]quinoline via an Aldol/Van Leusen/Staudinger/aza-Wittig sequence
  作者：Yu-Qing Shi、Li-De Liao、Ping He、Yang-Gen Hu、Hua Cheng、Song Wang、Jun-Jun Wu

  DOI：10.1080/00397911.2016.1204462

  日期：2016.8.17

  Leusen/Staudinger/aza-Wittig reaction for the preparation of the derivatives of 2H-pyrrolo[3,4-c]quinolines from 2-azidobenzaldehyde, acetyl compounds, and tosylmethyl isocyanide was developed. The process involves an aldol condensation of 2-azidobenzaldehyde with acetyl compound in base, a van Leusen reaction to form the key pyrrole intermediates, and then a Staudinger and intramolecular aza-Wittig reaction occurred

  摘要 建立了一种从 2-叠氮苯甲醛、乙酰化合物和甲苯磺酰甲基异氰化物制备 2H-吡咯并 [3,4-c] 喹啉衍生物的 aldol/van Leusen/Staudinger/aza-Wittig 反应。该过程包括2-叠氮基苯甲醛在碱中与乙酰基化合物的羟醛缩合，van Leusen反应形成关键的吡咯中间体，然后在加入三苯基膦的情况下发生Staudinger和分子内氮杂-Wittig反应以完成吡咯的形成。 3,4-c]喹啉环的高产率。图形概要
• 3-Phenacylideneoxindoles with tosylmethyl isocyanide and MeOH through C–C bond cleavage: facile synthesis of pyrrole and 2H-pyrrolo[3,4-c]quinoline derivatives
  作者：Rong Wang、Xiao-Ping Xu、Hua Meng、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1016/j.tet.2012.11.088

  日期：2013.2

  A novel reaction of 3-phenacylideneoxindoles (1) with tosylmethyl isocyanide (2a) and MeOH through C-C bond cleavage has been developed. The reaction proceeded under mild conditions, providing a powerful synthetic tool for the construction of pyrrole derivatives (3) from easily accessible starting materials and synthesis of 2H-pyrrolo[3,4-c]quinolines (4) by further dehydration of 3. (C) 2012 Elsevier Ltd. All rights reserved.
• TFA-catalyzed C–N bond activation of enamides with indoles: efficient synthesis of 3,3-bisindolylpropanoates and other bisindolylalkanes
  作者：Hai-Yan Xu、You Zi、Xiao-Ping Xu、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1016/j.tet.2012.11.098

  日期：2013.2

  An efficient TFA-catalyzed cleavage of C-N bonds in alkylation of indoles by tertiary enamides was described. A variety of bisindolylalkane derivatives, especially 3,3-bisindolylpropanoates, were expeditiously synthesized in good yields. (c) 2012 Elsevier Ltd. All rights reserved.
• One pot synthesis of pyrrolo[3,4-c]quinolinone/pyrrolo[3,4-c]quinoline derivatives from 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC)
  作者：Xin-Mou Lu、Jian Li、Zhong-Jian Cai、Rong Wang、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1039/c4ob01580k

  日期：——

  An efficient and practical synthetic approach to access to 2H-pyrrolo[3,4-c]quinolin-4(5H)-one/2H-pyrrolo[3,4-c]quinoline derivatives by the reaction of 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC) via a one pot van Leusen reaction and cyclization under basic conditions has been reported. The desired products could be obtained in moderate to good yields.

  据报道，在碱性条件下，2-氨基芳基丙烯酸酯/2-氨基查耳酮与对甲苯基甲基异氰酸酯（TosMIC）通过一锅范柳森反应和环化反应，可获得 2H-吡咯并[3,4-c]喹啉-4(5H)-酮/2H-吡咯并[3,4-c]喹啉衍生物，这是一种高效实用的合成方法。所需的产品可以中等到良好的收率获得。