1-(4-Bromo-phenyl)-3-phenyl-1H-benzo[4,5]imidazo[[1,2-c][1,2,3]triazole | 187589-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-Bromo-phenyl)-3-phenyl-1H-benzo[4,5]imidazo[[1,2-c][1,2,3]triazole
• 英文别名: 1-(4-Bromophenyl)-3-phenyltriazolo[1,5-a]benzimidazole
• CAS: 187589-71-5
• 化学式: C₂₀H₁₃BrN₄
• 分子量: 389.254
• InChiKey: FDWWBAAEASXCHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-Bromo-phenyl)-3-phenyl-1H-benzo[4,5]imidazo[[1,2-c][1,2,3]triazole 在 三氟乙酸 作用下， 反应 4.0h， 以90%的产率得到3-(benzimidazol-2-yl)-1-(4-bromophenyl)indazole
  参考文献：
  名称：

  Novel Thermal Rearrangement of Fused Diaryl-v-Triazolium Salts to Neutral Indazole Derivatives. Fused Azolium Salts. 16

  摘要：

  Alkylation of 1,3-diaryl-v-triazolo[1,5-a]benzimidazole (1) by trimethyloxonium salt afforded selectively the 4-methyl quaternary salt 2, whereas reaction with dimethyl sulfate at elevated temperature resulted in ring transformation, implying ring opening to a nitrenium cation and a subsequent electrophilic ring closure to give a benzimidazolylindazole product 5. Independent of the methylation, a similar easy thermal rearrangement was observed with alkylated 1,3-diaryl-v-triazolo[1,5-a]benzimidazolium (2 --> 4) and the related benzothiazolium salt (7 --> 8). Extension of the reaction to diaryl-v-triazolopyridinium salt (9 --> 10 + 11) allowed observation of an additional novel reaction path that provided further support for the supposed reaction mechanism.

  DOI：

  10.1021/jo961749o
• 作为产物：
  描述：

  2-benzoylbenzimidazole 4-bromophenylhydrazone 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以73%的产率得到1-(4-Bromo-phenyl)-3-phenyl-1H-benzo[4,5]imidazo[[1,2-c][1,2,3]triazole
  参考文献：
  名称：

  Novel Thermal Rearrangement of Fused Diaryl-v-Triazolium Salts to Neutral Indazole Derivatives. Fused Azolium Salts. 16

  摘要：

  Alkylation of 1,3-diaryl-v-triazolo[1,5-a]benzimidazole (1) by trimethyloxonium salt afforded selectively the 4-methyl quaternary salt 2, whereas reaction with dimethyl sulfate at elevated temperature resulted in ring transformation, implying ring opening to a nitrenium cation and a subsequent electrophilic ring closure to give a benzimidazolylindazole product 5. Independent of the methylation, a similar easy thermal rearrangement was observed with alkylated 1,3-diaryl-v-triazolo[1,5-a]benzimidazolium (2 --> 4) and the related benzothiazolium salt (7 --> 8). Extension of the reaction to diaryl-v-triazolopyridinium salt (9 --> 10 + 11) allowed observation of an additional novel reaction path that provided further support for the supposed reaction mechanism.

  DOI：

  10.1021/jo961749o