3-amino-5,6-dimethoxyindole-2-carbonitrile | 1206901-25-8

• 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: 3-amino-5,6-dimethoxyindole-2-carbonitrile
• 英文别名: 3-amino-5,6-dimethoxy-1H-indole-2-carbonitrile
• CAS: 1206901-25-8
• 化学式: C₁₁H₁₁N₃O₂
• 分子量: 217.227
• InChiKey: ODPATMZBMXTZIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  84.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-5,6-dimethoxyindole-2-carbonitrile 、 对甲苯磺酰氯 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以86%的产率得到5,6-dimethoxy-3-(p-tosylamino)indole-2-carbonitrile
  参考文献：
  名称：

  Detosylation of 3-amino-1-tosylindole-2-carbonitriles using DBU and thiophenol

  摘要：

  Attempted detosylation of the 3-amino-1-(p-tosylamino)indole-2-carbonitriles 4a-c using either K2CO3 in EtOH or DBU in PhH at reflux gives unexpectedly the 3-(N-p-tosylamino)indole-2-carbonitriles 5a-c, respectively in high yields. Nevertheless, treatment of 1-(p-tosylamino)indoles 4a-c with thiophenol and DBU in PhH at reflux gives the detosylated 3-aminoindole-2-carbonitriles 5a-c. Reaction mechanisms supporting the tosyl migration (4 -> 5) and the reductive detosylation (4 -> 2) are proposed. All new compounds are fully characterised. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.058
• 作为产物：
  描述：

  2-(cyanomethylamino)-4,5-dimethoxybenzonitrile 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 120.0 ℃ 、1.24 MPa 条件下， 反应 0.75h， 以89%的产率得到3-amino-5,6-dimethoxyindole-2-carbonitrile
  参考文献：
  名称：

  Microwave assisted synthesis of 3-aminoindole-2-carbonitriles from anthranilonitriles via N-unprotected 2-(cyanomethylamino)benzonitriles

  摘要：

  Anthranilonitrile 3a, 4,5-dimethoxyanthranilonitrile 3b and 5-nitroanthranilonitrile 3c, react with paraformaldehyde, KCN and ZnCl2 in acetic acid under acid catalysis (H2SO4) in a sealed tube at ca. 55 degrees C to give the corresponding 2-(cyanomethylamino)benzonitriles 4a-c in 96, 86 and 57% yields, respectively. Thorpe-Ziegler cyclisation of the N-unprotected 2-(cyanomethylamino)benzonitriles 4a-c with K2CO3 in EtOH at elevated temperatures and pressures using either microwave heating or conventional heating in a sealed tube gives 3-amino, 3-amino-5,6-dimethoxy, and 3-amino-5-nitro-indole-2-carbonitriles 2a-c in moderate to good yields. All new compounds are fully characterised. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.067

文献信息

• Detosylation of 3-amino-1-tosylindole-2-carbonitriles using DBU and thiophenol
  作者：Sophia S. Michaelidou、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2010.02.058

  日期：2010.4

  Attempted detosylation of the 3-amino-1-(p-tosylamino)indole-2-carbonitriles 4a-c using either K2CO3 in EtOH or DBU in PhH at reflux gives unexpectedly the 3-(N-p-tosylamino)indole-2-carbonitriles 5a-c, respectively in high yields. Nevertheless, treatment of 1-(p-tosylamino)indoles 4a-c with thiophenol and DBU in PhH at reflux gives the detosylated 3-aminoindole-2-carbonitriles 5a-c. Reaction mechanisms supporting the tosyl migration (4 -> 5) and the reductive detosylation (4 -> 2) are proposed. All new compounds are fully characterised. (C) 2010 Elsevier Ltd. All rights reserved.
• Microwave assisted synthesis of 3-aminoindole-2-carbonitriles from anthranilonitriles via N-unprotected 2-(cyanomethylamino)benzonitriles
  作者：Sophia S. Michaelidou、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2009.11.067

  日期：2010.1

  Anthranilonitrile 3a, 4,5-dimethoxyanthranilonitrile 3b and 5-nitroanthranilonitrile 3c, react with paraformaldehyde, KCN and ZnCl2 in acetic acid under acid catalysis (H2SO4) in a sealed tube at ca. 55 degrees C to give the corresponding 2-(cyanomethylamino)benzonitriles 4a-c in 96, 86 and 57% yields, respectively. Thorpe-Ziegler cyclisation of the N-unprotected 2-(cyanomethylamino)benzonitriles 4a-c with K2CO3 in EtOH at elevated temperatures and pressures using either microwave heating or conventional heating in a sealed tube gives 3-amino, 3-amino-5,6-dimethoxy, and 3-amino-5-nitro-indole-2-carbonitriles 2a-c in moderate to good yields. All new compounds are fully characterised. (C) 2009 Elsevier Ltd. All rights reserved.