1-(4-Bromo-phenyl)-3-(1-methyl-1H-benzoimidazol-2-yl)-1H-indazole

• 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-(1-methyl-1H-benzoimidazol-2-yl)-1H-indazole
• 英文别名: 1-(4-Bromophenyl)-3-(1-methylbenzimidazol-2-yl)indazole
• 化学式: C₂₁H₁₅BrN₄
• 分子量: 403.281
• InChiKey: HGWMKHYVGNYIKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(4-bromophenyl)-4-methyl-3-phenyl-v-triazolo[1,5-a]benzimidazolium fluoroborate 在 三氟乙酸 作用下， 反应 4.0h， 以89%的产率得到1-(4-Bromo-phenyl)-3-(1-methyl-1H-benzoimidazol-2-yl)-1H-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

文献信息

• Valence Bond Isomerization of Fused [1,2,3]Triazolium Salts with Bridgehead Nitrogen Atom. Fused Azolium Salts. 19^,
  作者：Mariann Béres、György Hajós、Zsuzsanna Riedl、Tibor Soós、Géza Timári、András Messmer

  DOI：10.1021/jo990328e

  日期：1999.7.1

  and some recent results reveals that this ring opening of fused [1,2,3]triazolium salts is a general phenomenon and is closely related to the well-known retro-electrocyclizations (called "1,5-dipolar cyclizations") of neutral fused [1,2,3]triazoles and tetrazoles.

  [1,2,3]三唑[1,5-a]喹啉（7），[1,2,3]三唑[1,5-b]异喹啉（8）和[1,2,3]三唑[ 1,5-a]吡嗪鎓盐（9）在三氟乙酸和/或1,2-二氯苯中加热时，会发生价键异构化，形成开环反应性中间体（例如，8生成13），可以参与（i）亲电取代作为氮阳离子产生吡唑和吲唑稠合的新杂环（例如形成13、14和15），（ii）伪电环化（例如，中间体19c生成吡唑并[3,4-b]吡嗪21） ，或（iii）在亲核加成中作为碳正离子（例如，在甲醇中加热时1生成甲氧基取代的加合物22）。比较这些结果和最近的一些结果后发现，稠合[1,2，
• Novel Thermal Rearrangement of Fused Diaryl-<i>v</i>-Triazolium Salts to Neutral Indazole Derivatives. Fused Azolium Salts. 16
  作者：T. Soós、Gy. Hajós、A. Messmer

  DOI：10.1021/jo961749o

  日期：1997.2.1

  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.