9-Amino-2,3-dihydro-5-(2-furyl)-2-propylpyrrolo<3,4-b>quinolin-1-one

• 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: 9-Amino-2,3-dihydro-5-(2-furyl)-2-propylpyrrolo<3,4-b>quinolin-1-one
• 英文别名: 9-amino-5-(furan-2-yl)-2-propyl-3H-pyrrolo[3,4-b]quinolin-1-one
• 化学式: C₁₈H₁₇N₃O₂
• 分子量: 307.352
• InChiKey: PNMMEOGWHTXWDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-Amino-3-(2-furyl)benzonitrile 在 sodium hydride 、 对甲苯磺酸 、 cadmium(II) chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.67h， 生成 9-Amino-2,3-dihydro-5-(2-furyl)-2-propylpyrrolo<3,4-b>quinolin-1-one
  参考文献：
  名称：

  Synthesis of Tricyclic Aminopyridines by a Cadmium Promoted Cyclization

  摘要：

  A novel cyclocondensation of o-amino nitriles with cyclic 1,3-diones has been developed as a synthetic route to assemble fused tricyclic aminopyridine derivatives. The reaction sequence involves the initial formation of an enaminone. The enaminone is then cyclized at 120 degrees C to 190 degrees C in the presence of Lewis acids which include zinc, cadmium and copper(I) salts. The cyclization may be promoted under more mild conditions by first deprotonating the enaminone to form the anion followed by exposure to cadmium(II) salts at 60 degrees C to 90 degrees C. Alternatively the enaminones may be reacted with organocadmium reagents such as dibutylcadmium to effect the deprotonation and cyclization directly at room temperature. Synthetic applications of these novel cadmium-mediated cyclizations are presented and mechanistic considerations discussed.

  DOI：

  10.1021/jo00121a048

文献信息

• Synthesis of Tricyclic Aminopyridines by a Cadmium Promoted Cyclization
  作者：James B. Campbell、Judy W. Firor

  DOI：10.1021/jo00121a048

  日期：1995.8

  A novel cyclocondensation of o-amino nitriles with cyclic 1,3-diones has been developed as a synthetic route to assemble fused tricyclic aminopyridine derivatives. The reaction sequence involves the initial formation of an enaminone. The enaminone is then cyclized at 120 degrees C to 190 degrees C in the presence of Lewis acids which include zinc, cadmium and copper(I) salts. The cyclization may be promoted under more mild conditions by first deprotonating the enaminone to form the anion followed by exposure to cadmium(II) salts at 60 degrees C to 90 degrees C. Alternatively the enaminones may be reacted with organocadmium reagents such as dibutylcadmium to effect the deprotonation and cyclization directly at room temperature. Synthetic applications of these novel cadmium-mediated cyclizations are presented and mechanistic considerations discussed.