2-(2-bromo-5-chlorophenyl)-1H-benzo[d]imidazole | 14225-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(2-bromo-5-chlorophenyl)-1H-benzo[d]imidazole
• 英文别名: 2-(2-bromo-5-chlorophenyl)-1H-benzimidazole
• CAS: 14225-85-5
• 化学式: C₁₃H₈BrClN₂
• mdl: MFCD30608485
• 分子量: 307.577
• InChiKey: RWOLJEYWZCGWCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  氰乙酸正丁酯 、 2-(2-bromo-5-chlorophenyl)-1H-benzo[d]imidazole 在 copper(l) iodide 、 potassium carbonate 、 六氢吡啶-alpha-羧酸 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以95%的产率得到Butyl 6-amino-2-chlorobenzimidazolo[2,1-a]isoquinoline-5-carboxylate
  参考文献：
  名称：

  Copper-Catalyzed Cascade Synthesis of Alkyl 6-Aminobenzimidazo[2,1-a]isoquinoline-5-carboxylates

  摘要：

  A convenient and efficient copper-catalyzed cascade method has been developed for synthesis of benzimidazoisoquinoline derivatives via reactions of readily available substituted 2-(2-halophenyObenzoimidazoles with alkyl cyanoacetates under mild condition, and the corresponding alkyl 6-aminobenzimidazo[2,1-a]isoquinoline-5-carboxylates were obtained in good to excellent yields. The novel method provides diverse and useful poly N-heterocyclic compounds for combinatorial chemistry and medicinal chemistry.

  DOI：

  10.1021/jo200508q
• 作为产物：
  描述：

  2-溴-5-氯苯甲醛 、 邻苯二胺 在 sodium hydrogensulfite 作用下， 生成 2-(2-bromo-5-chlorophenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  在微波辐射下通过无过渡金属串联 C(sp2)-N 键形成合成三核苯并咪唑融合的杂化支架

  摘要：

  通过无过渡金属的C( sp 2 )-N偶联和环化2-(2-溴芳基)-或2-(2-溴乙烯基)苯并咪唑与2-甲氧基-或微波辐射下的 2-芳氧基苯并咪唑。

  DOI：

  10.1002/ejoc.202100419

文献信息

• Copper-catalyzed cascade synthesis of benzimidazoquinazoline derivatives under mild condition
  作者：Shan Xu、Juyou Lu、Hua Fu

  DOI：10.1039/c1cc10383k

  日期：——

  A convenient and efficient copper-catalyzed cascade method has been developed for the synthesis of benzimidazoquinazoline derivatives via reactions of readily available substituted 2-(2-halophenyl)benzoimidazoles with amidines or guanidine under mild conditions (even at room temperature).

  已经开发了一种方便有效的铜催化级联方法，用于在温和的条件下（即使在室温下）通过容易获得的取代的2-（2-卤代苯基）苯并咪唑与am或胍的反应来合成苯并咪唑并喹唑啉衍生物。
• An efficient synthesis of 6-arylbenzo[4,5]imidazo[2,1-a]isoquinolines via sequential α-arylation of carbonyl and deacylation catalyzed by CuI
  作者：Wei-Qing Miao、Jian-Quan Liu、Xiang-Shan Wang

  DOI：10.1039/c7ob01022b

  日期：——

  Dibenzoyl methane was found to undergo α-arylation of carbonyl and deacylation reaction with 2-(2-bromophenyl)-1H-benzo[d]imidazoles catalyzed by CuI in the presence of Cs2CO3, and provided an efficient synthesis of 6-arylbenzo[4,5]imidazo[2,1-a]isoquinolines via subsequent intra-molecular nucleophilic addition and dehydration.

  发现二苯甲酰甲烷在Cs 2 CO 3存在下与CuI催化的2-（2-溴苯基）-1 H-苯并[ d ]咪唑发生羰基的α-芳基化反应和脱酰反应，并有效合成了6 -芳基苯并[4,5]咪唑并[2,1- a ]异喹啉通过随后的分子内亲核加成和脱水作用。
• General and efficient copper-catalyzed aerobic oxidative synthesis of N-fused heterocycles using amino acids as the nitrogen source
  作者：Qing Liu、Haijun Yang、Yuyang Jiang、Yufen Zhao、Hua Fu

  DOI：10.1039/c3ra41644e

  日期：——

  efficient copper-catalyzed aerobic oxidative method for the synthesis of N-fused heterocycles has been developed by using readily available α-amino acids as the nitrogen source. The reactions underwent N-arylation, aerobic oxidative dehydrogenation, intramolecular cyclization and dissociation of formic acid. This method should provide a general and practical strategy for the construction of N-fused

  通过使用容易获得的α-氨基酸作为氮源，已经开发了用于合成N-稠合杂环的通用且有效的铜催化的需氧氧化方法。反应进行了N-芳基化，好氧氧化脱氢，分子内环化和C的解离甲酸。该方法应为构建N-稠合杂环提供通用和实用的策略。
• Copper(I)-catalyzed α-arylation of carbonyl cascade reaction leading to benzo[4, 5] imidazo[1,2-f]phenanthridin-4(1H)-one derivatives
  作者：Fang Dong、Rong-Zhang Jin、Jian-Quan Liu、Xiang-Shan Wang

  DOI：10.1007/s11164-017-2975-7

  日期：2017.11

  α-arylation of carbonyl reaction and intra-molecular cyclization of 2-(2-bromophenyl)-1H-benzo[d]imidazoles with cyclohexane-1,3-diones was described in 1,4-dioxane catalyzed by Cu(I)/l-proline. It provided an efficient method for the synthesis of benzo[4, 5]imidazo[1,2-f] phenanthridin-4(1H)-ones with high efficiency in mild conditions. Graphical Abstract A sequential α-arylation of carbonyl reaction and intra-molecular

  摘要 在Cu（1,4-二恶烷）催化下，描述了羰基反应的顺序α-芳基化和2-（2-溴苯基）-1H-苯并[ d ]咪唑与环己烷-1,3-二酮的分子内环化I）/ l-脯氨酸 它为温和条件下高效合成苯并[4,5]咪唑并[1,2 - f ]菲啶-4（1 H）-提供了一种有效的方法。 图形概要 在Cu（）催化的1,4-二恶烷中描述了羰基反应的顺序α-芳基化和2-（2-溴苯基）-1 H-苯并[ d ]咪唑与环己烷-1,3-二酮的分子内环化I）/ l-脯氨酸
• Synthesis of Quinazolinones, Imidazo[1,2-<i>c</i> ]quinazolines and Imidazo[4,5-<i>c</i> ]quinolines through Tandem Reductive Amination of Aryl Halides and Oxidative Amination of C(sp³ )-H Bonds
  作者：Nitesh Kumar Nandwana、Shiv Dhiman、Hitesh Kumar Saini、Indresh Kumar、Anil Kumar

  DOI：10.1002/ejoc.201601329

  日期：2017.1.18

  2-c]quinazolines and imidazo[4,5-c]quinolines. The reaction involves a copper-catalyzed reductive amination through azidation followed by reduction and oxidative amination of C(sp3)–H bonds of N,N-dimethylacetamide in the presence of TBHP (tert-butylhydroperoxide) as oxidant. The method uses the easily available sodium azide as a nitrogen source and DMA (N,N-dimethylacetamide) as a one-carbon source for the

  已经描述了用于合成喹唑啉酮、咪唑并[1,2-c]喹唑啉和咪唑并[4,5-c]喹啉的串联多组分方法。该反应涉及铜催化的叠氮化还原胺化，然后在 TBHP（叔丁基氢过氧化物）作为氧化剂的存在下还原和氧化胺化 N,N-二甲基乙酰胺的 C(sp3)-H 键。该方法使用容易获得的叠氮化钠作为氮源，使用 DMA（N,N-二甲基乙酰胺）作为单碳源合成这些 N-稠合杂环，收率良好。该反应也可用于克级合成。