2-benzyl-3-thioxo-2H-imidazo[1,5-b]isoquinoline-1,5-dione | 860030-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-benzyl-3-thioxo-2H-imidazo[1,5-b]isoquinoline-1,5-dione
• 英文别名: 2-Benzyl-3-sulfanylideneimidazo[1,5-b]isoquinoline-1,5-dione
• CAS: 860030-12-2
• 化学式: C₁₈H₁₂N₂O₂S
• 分子量: 320.371
• InChiKey: SJRICKKVGJKTDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzyl-3-thioxo-2H-imidazo[1,5-b]isoquinoline-1,5-dione 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 反应 1.0h， 以78%的产率得到2-benzyl-2H-imidazo[1,5-b]isoquinoline-1,5-dione
  参考文献：
  名称：

  A novel synthesis of 2-substituted 2H-imidazo[1,5-b]isoquinoline-1,5-diones by in situ desulfurization

  摘要：

  A novel synthesis of 2-substituted 2H-imidazo[1,5-b]isoquinoline-1,5-diones by reductive desulfurization of a variety of 2-substituted 3-thioxo-2H-imidazo[1,5-b]isoquinoline-1,5-diones is reported with nickel boride in dry methanol at ambient temperature.

  DOI：

  10.1007/s10593-008-0045-1
• 作为产物：
  描述：

  邻羧基苯甲醛 在 sodium acetate 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 2-benzyl-3-thioxo-2H-imidazo[1,5-b]isoquinoline-1,5-dione
  参考文献：
  名称：

  SYNTHESIS OF 15H-ISOQUINO[2′,3′:3,4]IMIDAZO[2,1-B]QUINAZOLINE-7,13,15-TRIONES AND 14H-ISOQUINO[2′,3′:3,4]IMIDAZO[2,1-B]BENZO[G]QUINAZOLINE-8,14,16-TRIONE AS NEW POLYCYCLIC FUSED-RING SYSTEMS

  摘要：

  3-Thioxo-2H-imidazo[1,5-b]isoquinoline-1,5-dione (3) and 2-substituted-3-thioxo-2H-imidazo[1,5-b]isoquinoline-1,5-diones(4a-l) were prepared from the reaction of 2-thioliydantoin. (2) and 3-substituted 2-thiohydantoin (5a-l) with 2-formyl benzoic acid (1). Alkylation of 3 under an anhydrous basic conditions afforded 4a-i. The alkylation of 3 in. aqueous basic solution, afforded 3-(alkyl-mercapto)imidazo[1,5-b]isoquinoline-1,5-diones (7a,b). Reactions of the aromatic amino acids 9a,b and 12 with 7a afforded 2-(2H-1,5dioxoimidazo[1,5-b]isoquinazolin-3-ylideneamino)benzoic acids (10a,b) and 3-(2H-1,5-dioxoimidazo[1,5-b]isoquinazolin-3-ylideneamino)-2-naphthalenecarboxylic acid (13), which were then cyclyzed by heating in acetic anhydride to afford 15H-isoquino[2',3':3,4]-imidazo[2,1-b]quinazoline-7,13,15-triones (11a,b) and 14H-isoquino[2',3':3,4]imidazo[2,1-b]benzo[g]quinazoline-8,14,16-trione (14). Some of the new compounds were tested for their antitumor activities.

  DOI：

  10.1080/104265090507533

文献信息

• SYNTHESIS OF 15<i>H</i>-ISOQUINO[2′,3′:3,4]IMIDAZO[2,1-<i>B</i>]QUINAZOLINE-7,13,15-TRIONES AND 14<i>H</i>-ISOQUINO[2′,3′:3,4]IMIDAZO[2,1-<i>B</i>]BENZO[<i>G</i>]QUINAZOLINE-8,14,16-TRIONE AS NEW POLYCYCLIC FUSED-RING SYSTEMS
  作者：Ahmed I. Khodair、Jean-Pierre Gesson、El-Sayed H. El-Ashry

  DOI：10.1080/104265090507533

  日期：2004.12.1

  3-Thioxo-2H-imidazo[1,5-b]isoquinoline-1,5-dione (3) and 2-substituted-3-thioxo-2H-imidazo[1,5-b]isoquinoline-1,5-diones(4a-l) were prepared from the reaction of 2-thioliydantoin. (2) and 3-substituted 2-thiohydantoin (5a-l) with 2-formyl benzoic acid (1). Alkylation of 3 under an anhydrous basic conditions afforded 4a-i. The alkylation of 3 in. aqueous basic solution, afforded 3-(alkyl-mercapto)imidazo[1,5-b]isoquinoline-1,5-diones (7a,b). Reactions of the aromatic amino acids 9a,b and 12 with 7a afforded 2-(2H-1,5dioxoimidazo[1,5-b]isoquinazolin-3-ylideneamino)benzoic acids (10a,b) and 3-(2H-1,5-dioxoimidazo[1,5-b]isoquinazolin-3-ylideneamino)-2-naphthalenecarboxylic acid (13), which were then cyclyzed by heating in acetic anhydride to afford 15H-isoquino[2',3':3,4]-imidazo[2,1-b]quinazoline-7,13,15-triones (11a,b) and 14H-isoquino[2',3':3,4]imidazo[2,1-b]benzo[g]quinazoline-8,14,16-trione (14). Some of the new compounds were tested for their antitumor activities.
• A novel synthesis of 2-substituted 2H-imidazo[1,5-b]isoquinoline-1,5-diones by in situ desulfurization
  作者：Jitender M. Khurana、Vandana Sharma

  DOI：10.1007/s10593-008-0045-1

  日期：2008.3

  A novel synthesis of 2-substituted 2H-imidazo[1,5-b]isoquinoline-1,5-diones by reductive desulfurization of a variety of 2-substituted 3-thioxo-2H-imidazo[1,5-b]isoquinoline-1,5-diones is reported with nickel boride in dry methanol at ambient temperature.