1-{[(4-Chlorophenyl)methylidene]amino}-4-phenyl-1H-imidazol-2-amine | 465516-19-2

• 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-Chlorophenyl)methylidene]amino}-4-phenyl-1H-imidazol-2-amine
• 英文别名: 1-[(4-chlorophenyl)methylideneamino]-4-phenylimidazol-2-amine
• CAS: 465516-19-2
• 化学式: C₁₆H₁₃ClN₄
• 分子量: 296.759
• InChiKey: QCILAKLWCDCMEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-{[(4-Chlorophenyl)methylidene]amino}-4-phenyl-1H-imidazol-2-amine 、 丁炔二酸二甲酯 以 苯 为溶剂， 反应 0.17h， 以68%的产率得到
  参考文献：
  名称：

  Synthesis of Nitrogen-Containing Heterocycles 12. Reactions of 2-Amino-1-benzylideneamino-1H-imidazoles with Dimethyl Acetylenedicarboxylate

  摘要：

  2-Amino-4-aryl-l-benzylideneamino-IH-imidazoles (1) reacted with dimethyl acetylenedicarboxylate (DMAD) in benzene to give dimethyl 2-amino-1-benzylidene-amino-1H-pyrrole-3,4-dicarboxylates (3), benzonitriles (4) and dimethyl 1-(2-amino-1-benzylideneamino-4-aryl-1H-imidazole-5-yl)fumarates (5) in moderate to high yields. Compounds 3 and 4 were considered as the reaction products of the intermediary Diels-Alder adducts, dimethyl 1-amino-3-aryl-7-benzylideneamino-2,7-diazabicylo[2.2.1]hepta-2,5-diene-5,6-dicarboxylates (2), which were not isolated and decomposed in a retro Diels-Alder reaction. The products 5 resulted from a Michael conjugate addition reaction of 1 to DMAD.

  DOI：

  10.3987/com-08-11558
• 作为产物：
  描述：

  4-氯苯甲醛 、 1,3-环己二酮 、 4-苯基-1H-咪唑-1,2-二胺 以 甲醇 为溶剂， 反应 2.0h， 以72%的产率得到3-amino-10-(4-chlorophenyl)-1-phenyl-6,7,8,10-tetrahydroimidazo[1,5-b]cinnolin-9(5H)-one
  参考文献：
  名称：

  Cascade cyclization of 1,2-diamino-4-phenylimidazole with aromatic aldehydes and cyclohexanediones

  摘要：

  The three-component condensation of 1,2-diamino-4-phenylimidazole with aromatic aldehydes and 1,3-cyclohexanediones occurred regioselectively and afforded 3-amino-1-phenyl-10-aryl-7,8-dihydroimidazo[1,5-b] cinnolin-9(5H,6H,10H)-ones.

  DOI：

  10.1134/s1070428012020182

文献信息

• Cascade cyclization of 1,2-diamino-4-phenylimidazole with aromatic aldehydes and cyclohexanediones
  作者：V. V. Lipson、N. V. Svetlichnaya、M. G. Shirobokov、V. I. Musatov、O. V. Shishkin、S. V. Shishkina

  DOI：10.1134/s1070428012020182

  日期：2012.2

  The three-component condensation of 1,2-diamino-4-phenylimidazole with aromatic aldehydes and 1,3-cyclohexanediones occurred regioselectively and afforded 3-amino-1-phenyl-10-aryl-7,8-dihydroimidazo[1,5-b] cinnolin-9(5H,6H,10H)-ones.
• Synthesis of Nitrogen-Containing Heterocycles 12. Reactions of 2-Amino-1-benzylideneamino-1H-imidazoles with Dimethyl Acetylenedicarboxylate
  作者：Yoshiko Miyamoto

  DOI：10.3987/com-08-11558

  日期：——

  2-Amino-4-aryl-l-benzylideneamino-IH-imidazoles (1) reacted with dimethyl acetylenedicarboxylate (DMAD) in benzene to give dimethyl 2-amino-1-benzylidene-amino-1H-pyrrole-3,4-dicarboxylates (3), benzonitriles (4) and dimethyl 1-(2-amino-1-benzylideneamino-4-aryl-1H-imidazole-5-yl)fumarates (5) in moderate to high yields. Compounds 3 and 4 were considered as the reaction products of the intermediary Diels-Alder adducts, dimethyl 1-amino-3-aryl-7-benzylideneamino-2,7-diazabicylo[2.2.1]hepta-2,5-diene-5,6-dicarboxylates (2), which were not isolated and decomposed in a retro Diels-Alder reaction. The products 5 resulted from a Michael conjugate addition reaction of 1 to DMAD.