4-(1-cyclohexyl-2-{[(1E,2E)-3-(piperidin-1-yl)prop-2-enylidene]amino}-1H-imidazol-5-yl)benzonitrile | 1042275-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(1-cyclohexyl-2-{[(1E,2E)-3-(piperidin-1-yl)prop-2-enylidene]amino}-1H-imidazol-5-yl)benzonitrile
• CAS: 1042275-88-6
• 化学式: C₂₄H₂₉N₅
• 分子量: 387.528
• InChiKey: LEBVXRNSGREHFV-RSYDAIIGSA-N

反应信息

• 作为反应物：
  描述：

  4-(1-cyclohexyl-2-{[(1E,2E)-3-(piperidin-1-yl)prop-2-enylidene]amino}-1H-imidazol-5-yl)benzonitrile 在 哌啶 、 三乙胺盐酸盐 作用下， 以 乙腈 为溶剂， 以100%的产率得到4-(2-amino-1-cyclohexyl-1H-imidazol-5-yl)benzonitrile
  参考文献：
  名称：

  A Divergent Synthesis of Substituted 2-Aminoimidazoles from 2-Aminopyrimidines

  摘要：

  A new divergent and efficient synthesis of substituted 2-aminoimidazoles 5 and 6 has been developed starting from the readily available 2-aminopyrimidines 1 and alpha-broinocarbonyl compounds 2, Using conventional heating or microwave irradiation. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1 -iumsalts 4 with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles 5, when the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts 3, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles 6. The relevant pathway of transformations was identified by characterization of the intermediates.

  DOI：

  10.1021/jo8008758
• 作为产物：
  描述：

  哌啶 、 1-cyclohexyl-2-(4-cyanophenyl)imidazo[1,2-a]pyrimidin-1-ium perchlorate 以 乙腈 为溶剂， 反应 0.17h， 以76%的产率得到4-(1-cyclohexyl-2-{[(1E,2E)-3-(piperidin-1-yl)prop-2-enylidene]amino}-1H-imidazol-5-yl)benzonitrile
  参考文献：
  名称：

  A Divergent Synthesis of Substituted 2-Aminoimidazoles from 2-Aminopyrimidines

  摘要：

  A new divergent and efficient synthesis of substituted 2-aminoimidazoles 5 and 6 has been developed starting from the readily available 2-aminopyrimidines 1 and alpha-broinocarbonyl compounds 2, Using conventional heating or microwave irradiation. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1 -iumsalts 4 with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles 5, when the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts 3, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles 6. The relevant pathway of transformations was identified by characterization of the intermediates.

  DOI：

  10.1021/jo8008758