4-(5-methyl-1H-benzo[d]imidazol-2-yl)tetrazolo[1,5-a]quinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(5-methyl-1H-benzo[d]imidazol-2-yl)tetrazolo[1,5-a]quinoline
• 英文别名: 4-(6-methyl-1H-benzimidazol-2-yl)tetrazolo[1,5-a]quinoline
• 化学式: C₁₇H₁₂N₆
• 分子量: 300.322
• InChiKey: NVNMVHARUBRYBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯-3-喹啉甲醛 在 sodium azide 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.07h， 生成 4-(5-methyl-1H-benzo[d]imidazol-2-yl)tetrazolo[1,5-a]quinoline
  参考文献：
  名称：

  Microwave-assisted synthesis of some new tetrazolo[1,5-a]quinoline-based benzimidazoles catalyzed by p-TsOH and investigation of their antimicrobial activity

  摘要：

  Keeping the objective to build up a new structural class of potent antimicrobials, a series of some new 4-Benzimidazol-2-yl tetrazolo[1,5-a]quinoline derivatives has been synthesized by reaction of tetrazolo[1,5-a]quinoline-4-carbaldehyde and o-phenylenediamine in the presence of an organocatalyst p-TsOH under the influence of microwave irradiation. The identity of all the compounds has been established by H-1 NMR, C-13 NMR, FTIR, and elemental analysis. The synthesized compounds were subjected to in vitro antimicrobial screening against a representative panel of pathogenic strains including three Gram-positive bacteria (Bacillus subtilis, Clostridium tetani, and Streptococcus pneumoniae) and three Gram-negative bacteria (Escherichia coli, Salmonella typhi, and Vibrio cholerae) as well as two fungal organisms (Aspergillus fumigatus and Candida albicans) by employing broth microdilution method. Of the compounds studied, compound 5e demonstrated significant activity against a Gram-positive bacteria Bacillus subtilis.

  DOI：

  10.1007/s00044-010-9388-0

文献信息

• Highly reusable support‐free copper(II) complex of <i>para</i> ‐hydroxy‐substituted salen: Novel, efficient and versatile catalyst for C─N bond forming reactions
  作者：Hashem Sharghi、Mahdi Aberi、Pezhman Shiri

  DOI：10.1002/aoc.3761

  日期：2017.11

  An air‐stable, highly active and versatile method for C─N bond forming reactions is reported. Under mild conditions using a highly reusable support‐free Cu(II)–salen complex, structurally diverse N‐aryl‐substituted compounds were obtained via direct C─N bond forming reaction of HN‐heterocycles with aryl iodides or three‐component C─N bond forming reaction of 2‐bromobenzaldehyde, aniline derivatives

  据报道，一种稳定，高活性和通用的CN键形成反应的方法。在温和条件下，使用高度可重复使用的无载体铜（II）-沙仑配合物，结构多样的氮芳基取代的化合物是通过HN杂环与芳基碘化物的直接C-N键形成反应或2-溴苯甲醛，苯胺衍生物和叠氮化钠的三组分C-N键形成反应获得的，收率良好。在环境条件下，在催化剂存在下，苯并咪唑衍生物的C-N键形成反应也进行了。使用该方法生产了一系列带有吗啉，四唑和喹喔啉主链的杂苯并咪唑。所有反应均在短时间内在空气中进行。在9 H-咔唑与碘苯的直接交叉偶联反应中，Cu（II）催化剂最多可重复使用八次，而催化活性不会降低。
• Microwave-assisted synthesis of some new tetrazolo[1,5-a]quinoline-based benzimidazoles catalyzed by p-TsOH and investigation of their antimicrobial activity
  作者：Divyesh C. Mungra、Manish P. Patel、Ranjan G. Patel

  DOI：10.1007/s00044-010-9388-0

  日期：2011.7

  Keeping the objective to build up a new structural class of potent antimicrobials, a series of some new 4-Benzimidazol-2-yl tetrazolo[1,5-a]quinoline derivatives has been synthesized by reaction of tetrazolo[1,5-a]quinoline-4-carbaldehyde and o-phenylenediamine in the presence of an organocatalyst p-TsOH under the influence of microwave irradiation. The identity of all the compounds has been established by H-1 NMR, C-13 NMR, FTIR, and elemental analysis. The synthesized compounds were subjected to in vitro antimicrobial screening against a representative panel of pathogenic strains including three Gram-positive bacteria (Bacillus subtilis, Clostridium tetani, and Streptococcus pneumoniae) and three Gram-negative bacteria (Escherichia coli, Salmonella typhi, and Vibrio cholerae) as well as two fungal organisms (Aspergillus fumigatus and Candida albicans) by employing broth microdilution method. Of the compounds studied, compound 5e demonstrated significant activity against a Gram-positive bacteria Bacillus subtilis.