9-(4-amino-1-methyl-1H-imidazol-5-yl)-9H-carbazole | 1001024-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-(4-amino-1-methyl-1H-imidazol-5-yl)-9H-carbazole
• 英文别名: 5-Carbazol-9-yl-1-methylimidazol-4-amine；5-carbazol-9-yl-1-methylimidazol-4-amine
• CAS: 1001024-08-3
• 化学式: C₁₆H₁₄N₄
• 分子量: 262.314
• InChiKey: VPAXQJLKZILFBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  48.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-(4-amino-1-methyl-1H-imidazol-5-yl)-9H-carbazole 、 对甲基苯甲酰氯 以 四氢呋喃 为溶剂， 反应 1.5h， 以79%的产率得到N-[5-(carbazol-9-yl)-1-methyl-1H-imidazol-4-yl]-4-methylbenzamide
  参考文献：
  名称：

  Synthesis of 8-substituted 12-methyl-12H-imidazo[4',5': 2, 3][1,4]diazepino[6,7,1-jk]carbazoles

  摘要：

  A synthesis of model 8-substituted-12-methyl-12H-imidazo[4', 5': 2, 3][1,4]-diazepino[6,7,1-jk]carbazoles (10a-c), based on the classical Bischler-Napieralski method, is described. Thus interaction of carbazole with 5-chloro-1-methyl-4-nitro-1H-imidazole (in the presence of sodium hydride) produced the corresponding 9-(1-methyl-4-nitro-1H-imidazole-5-yl)-9H-carbazole (7). Chemical reduction of the nitro group of 7 into the respective amino derivative 8, and subsequent acylation of the resulting amino group furnished the respective amides 9a-c. Cyclocondensation of the latter amides, using polyphosphoric acid under Bischler-Napieralski reaction conditions, delivered the target compounds 10a-c. The structures of these new pentacyclic heterocycles were supported by IR, MS, and NMR spectral data.

  DOI：

  10.1016/s0385-5414(07)81203-2
• 作为产物：
  描述：

  9-(1-methyl-4-nitro-1H-imidazol-5-yl)-9H-carbazole 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以67%的产率得到9-(4-amino-1-methyl-1H-imidazol-5-yl)-9H-carbazole
  参考文献：
  名称：

  Synthesis of 8-substituted 12-methyl-12H-imidazo[4',5': 2, 3][1,4]diazepino[6,7,1-jk]carbazoles

  摘要：

  A synthesis of model 8-substituted-12-methyl-12H-imidazo[4', 5': 2, 3][1,4]-diazepino[6,7,1-jk]carbazoles (10a-c), based on the classical Bischler-Napieralski method, is described. Thus interaction of carbazole with 5-chloro-1-methyl-4-nitro-1H-imidazole (in the presence of sodium hydride) produced the corresponding 9-(1-methyl-4-nitro-1H-imidazole-5-yl)-9H-carbazole (7). Chemical reduction of the nitro group of 7 into the respective amino derivative 8, and subsequent acylation of the resulting amino group furnished the respective amides 9a-c. Cyclocondensation of the latter amides, using polyphosphoric acid under Bischler-Napieralski reaction conditions, delivered the target compounds 10a-c. The structures of these new pentacyclic heterocycles were supported by IR, MS, and NMR spectral data.

  DOI：

  10.1016/s0385-5414(07)81203-2

文献信息

• Synthesis of 8-substituted 12-methyl-12H-imidazo[4',5': 2, 3][1,4]diazepino[6,7,1-jk]carbazoles
  作者：K ABUSAFIEH、F DARRAS、M AYOUB、M ELABADELAH、S SABRI、W VOELTER

  DOI：10.1016/s0385-5414(07)81203-2

  日期：2007.12.1

  A synthesis of model 8-substituted-12-methyl-12H-imidazo[4', 5': 2, 3][1,4]-diazepino[6,7,1-jk]carbazoles (10a-c), based on the classical Bischler-Napieralski method, is described. Thus interaction of carbazole with 5-chloro-1-methyl-4-nitro-1H-imidazole (in the presence of sodium hydride) produced the corresponding 9-(1-methyl-4-nitro-1H-imidazole-5-yl)-9H-carbazole (7). Chemical reduction of the nitro group of 7 into the respective amino derivative 8, and subsequent acylation of the resulting amino group furnished the respective amides 9a-c. Cyclocondensation of the latter amides, using polyphosphoric acid under Bischler-Napieralski reaction conditions, delivered the target compounds 10a-c. The structures of these new pentacyclic heterocycles were supported by IR, MS, and NMR spectral data.