2-碘-6H-苯并咪唑并[2,1-b]喹唑啉-12-酮 | 32701-17-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 2-碘-6H-苯并咪唑并[2,1-b]喹唑啉-12-酮
• 英文名称: 2-iodobenzimidazo[2,1-b]quinazolin-12(6H)-one
• 英文别名: 2-iodo-5H-benzo[4,5]imidazo[2,1-b]quinazolin-12-one；2-iodobenzimidazo[2,1-b]quinazolin-12(6H)one；2-Iodo-benzimidazo<1,2-b>chinazolin-12(6H)-on；Benzimidazo(2,1-b)quinazolin-12(6H)-one, 2-iodo-；2-iodo-6H-benzimidazolo[2,1-b]quinazolin-12-one
• CAS: 32701-17-0
• 化学式: C₁₄H₈IN₃O
• 分子量: 361.142
• InChiKey: GFYBDLLHTVOEHC-UHFFFAOYSA-N

物化性质

• 沸点：
  612.0±57.0 °C(Predicted)
• 密度：
  2.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-thio-3-methyl-6-iodo-4(3H)-quinazolinone 在 sodium hydroxide 作用下， 以 melt 、 水 为溶剂， 反应 21.0h， 生成 2-碘-6H-苯并咪唑并[2,1-b]喹唑啉-12-酮
  参考文献：
  名称：

  New general synthesis of benzo[4,5]imidazo[1,2-a]pyrimidine and benzo[4,5]imidazo[2,1-b]quinazoline derivatives

  摘要：

  The reactions of benzene-1,2-diamine with 5-substituted 2-(alkylsulfanyl)-4-methylpyrimidin-6(1H)-ones and 2-(propylsulfanyl)- and 5-iodo-2-(propylsulfanyl)-3,4-dihydroquinazolines at 175-185A degrees C under solvent-free conditions unexpectedly afforded benzo[4,5]imidazo[1,2-a]pyrimidine, benzo[4,5]imidazo[2,1-b]-quinazoline, and 2,2'-(benzene-1,2-diyldiimino)bis[pyrimidin-4(3H)-ones]. The described reaction is the first example of synthesis of these heterocyclic systems by fusion of benzimidazole to pyrimidine or quinazoline and is likely to follow ANRORC mechanism.

  DOI：

  10.1134/s1070428016070150

文献信息

• Immunosuppressants
  申请人：Eli Lilly and Company

  公开号：US04000275A1

  公开（公告）日：1976-12-28

  Benzimidazo[2,1-b]quinazolin-12(6H)ones, immunosuppressives and agents for treatment of auto-immune diseases, are prepared via (1) reacting a 2-chlorobenzimidazole with an anthranilic acid or ester; (2) reacting a 2-aminobenzimidazole with an anthranilic acid or ester in the presence of trifluoroacetic acid or (3) reacting a 2-methylmercaptobenzimidazole with an anthraniloyl halide hydrohalide.

  Benzimidazo[2,1-b]quinazolin-12(6H)ones是一种免疫抑制剂和治疗自身免疫疾病的药物，制备方法如下：(1)将2-氯苯并咪唑与吗啉酸或酯反应；(2)在三氟乙酸存在下，将2-氨基苯并咪唑与吗啉酸或酯反应；(3)将2-甲基硫代苯并咪唑与吗啉酰卤化物水合物反应。
• US4000275A
  申请人：——

  公开号：US4000275A

  公开（公告）日：1976-12-28
• New general synthesis of benzo[4,5]imidazo[1,2-a]pyrimidine and benzo[4,5]imidazo[2,1-b]quinazoline derivatives
  作者：A. A. Harutyunyan

  DOI：10.1134/s1070428016070150

  日期：2016.7

  The reactions of benzene-1,2-diamine with 5-substituted 2-(alkylsulfanyl)-4-methylpyrimidin-6(1H)-ones and 2-(propylsulfanyl)- and 5-iodo-2-(propylsulfanyl)-3,4-dihydroquinazolines at 175-185A degrees C under solvent-free conditions unexpectedly afforded benzo[4,5]imidazo[1,2-a]pyrimidine, benzo[4,5]imidazo[2,1-b]-quinazoline, and 2,2'-(benzene-1,2-diyldiimino)bis[pyrimidin-4(3H)-ones]. The described reaction is the first example of synthesis of these heterocyclic systems by fusion of benzimidazole to pyrimidine or quinazoline and is likely to follow ANRORC mechanism.