13-(p-tolyl)-3H-benzo[h]pyrazolo[4,3-a]acridine-11,12-dione | 1569467-60-2

• 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: 13-(p-tolyl)-3H-benzo[h]pyrazolo[4,3-a]acridine-11,12-dione
• CAS: 1569467-60-2
• 化学式: C₂₅H₁₅N₃O₂
• 分子量: 389.413
• InChiKey: HITPTGFYMARALS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  30.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  75.71
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  13-(p-tolyl)-3H-benzo[h]pyrazolo[4,3-a]acridine-11,12-dione 、 4-甲氧基苯甲醛 在 ammonium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.47h， 以80%的产率得到2-(4-methoxyphenyl)-14-(p-tolyl)-11H-benzo[c]oxazolo[5,4-a]pyrazolo[3,4-j]acridine
  参考文献：
  名称：

  Regioselective Multicomponent Domino Reactions Providing Rapid and Efficient Routes to Fused Acridines

  摘要：

  Regioselective three-component reactions of aromatic aldehydes with indazol-5-amine and 2-hydroxy-1,4-naphthoquinone in HOAc under microwave irradiation have been developed. In this one-pot reaction, a series of new pyrazole-fused benzo[h]acridine derivatives with 1,2-diketone unit were synthesized with high chemical yields. The resulting pyrazole-fused acridines were employed to further react with aldehydes and ammonium acetate to give polycyclic oxazole-fused pyrazolo[3,4-j]acridines. The present green synthesis shows several advantages including operational simplicity and fast reaction rates, which makes it a useful and attractive process of library generation for drug discovery.

  DOI：

  10.3987/com-13-s(s)65
• 作为产物：
  描述：

  2-羟基-1,4-萘醌 、 5-氨基吲唑 、 对甲基苯甲醛 在 溶剂黄146 作用下， 反应 0.27h， 以79%的产率得到13-(p-tolyl)-3H-benzo[h]pyrazolo[4,3-a]acridine-11,12-dione
  参考文献：
  名称：

  Regioselective Multicomponent Domino Reactions Providing Rapid and Efficient Routes to Fused Acridines

  摘要：

  Regioselective three-component reactions of aromatic aldehydes with indazol-5-amine and 2-hydroxy-1,4-naphthoquinone in HOAc under microwave irradiation have been developed. In this one-pot reaction, a series of new pyrazole-fused benzo[h]acridine derivatives with 1,2-diketone unit were synthesized with high chemical yields. The resulting pyrazole-fused acridines were employed to further react with aldehydes and ammonium acetate to give polycyclic oxazole-fused pyrazolo[3,4-j]acridines. The present green synthesis shows several advantages including operational simplicity and fast reaction rates, which makes it a useful and attractive process of library generation for drug discovery.

  DOI：

  10.3987/com-13-s(s)65