2,3-bis(4-tolylimino)-2,3-dihydroimidazo[1,2-a]pyridine | 347187-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2,3-bis(4-tolylimino)-2,3-dihydroimidazo[1,2-a]pyridine
• 英文别名: 2,3-bis(p-tolylimino)-2H-imidazo[1,2-a]pyridine；2-N,3-N-bis(4-methylphenyl)imidazo[1,2-a]pyridine-2,3-diimine
• CAS: 347187-48-8
• 化学式: C₂₁H₁₈N₄
• 分子量: 326.401
• InChiKey: HDYXOWFVDMYGTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  40.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-bis(4-tolylimino)-2,3-dihydroimidazo[1,2-a]pyridine 在 sodium dithionite 作用下， 以 丙酮 为溶剂， 以100%的产率得到N2,N3-di-p-tolyl-imidazo[1,2-a]-pyridine-2,3-diamine
  参考文献：
  名称：

  4H-Imidazoles as functional dyes: synthesis of bichromophores and extension of the merocyanine system

  摘要：

  A series of bichromophores consisting of a 'classical' chromophore and 4H-imidazoles were synthesized starting from appropriate cyano and carboxy functionalized systems. In their UV-vis spectra, an additive absorption of both chromophores was detected making them wide range-absorbing dyes. In addition, new properties as redox activity, pH-switchability and metal-chelating substructures are newly introduced into the molecules. In order to achieve more bathochromic absorbing systems, the chromophore of 4H-imidazoles was extended. The 4H-imidazo-[1,2-a]-pyridines, which are easily accessible by cyclization of 2-aminopyridines with bis-imidoylchlorides, show long wavelength absorptions up to 616 nm. Their reduction reversibly yields yellow, blue fluorescent 1-azaindolizines. In contrast to leucoforms reduction products show a high stability towards oxygen and could only forms of 4H-imidazoles, be reoxidized to their starting materials by oxidation agents, such as DDQ. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.117
• 作为产物：
  描述：

  N2,N3-di-p-tolyl-imidazo[1,2-a]-pyridine-2,3-diamine 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 2,3-bis(4-tolylimino)-2,3-dihydroimidazo[1,2-a]pyridine
  参考文献：
  名称：

  4H-Imidazoles as functional dyes: synthesis of bichromophores and extension of the merocyanine system

  摘要：

  A series of bichromophores consisting of a 'classical' chromophore and 4H-imidazoles were synthesized starting from appropriate cyano and carboxy functionalized systems. In their UV-vis spectra, an additive absorption of both chromophores was detected making them wide range-absorbing dyes. In addition, new properties as redox activity, pH-switchability and metal-chelating substructures are newly introduced into the molecules. In order to achieve more bathochromic absorbing systems, the chromophore of 4H-imidazoles was extended. The 4H-imidazo-[1,2-a]-pyridines, which are easily accessible by cyclization of 2-aminopyridines with bis-imidoylchlorides, show long wavelength absorptions up to 616 nm. Their reduction reversibly yields yellow, blue fluorescent 1-azaindolizines. In contrast to leucoforms reduction products show a high stability towards oxygen and could only forms of 4H-imidazoles, be reoxidized to their starting materials by oxidation agents, such as DDQ. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.117

文献信息

• Langer, Peter; Wuckelt, Joerg; Doering, Manfred, European Journal of Organic Chemistry, 2001, # 8, p. 1503 - 1509
  作者：Langer, Peter、Wuckelt, Joerg、Doering, Manfred、Goerls, Helmar

  DOI：——

  日期：——
• 4H-Imidazoles as functional dyes: synthesis of bichromophores and extension of the merocyanine system
  作者：Martin Matschke、Jörg Blumhoff、Rainer Beckert

  DOI：10.1016/j.tet.2008.05.117

  日期：2008.8

  A series of bichromophores consisting of a 'classical' chromophore and 4H-imidazoles were synthesized starting from appropriate cyano and carboxy functionalized systems. In their UV-vis spectra, an additive absorption of both chromophores was detected making them wide range-absorbing dyes. In addition, new properties as redox activity, pH-switchability and metal-chelating substructures are newly introduced into the molecules. In order to achieve more bathochromic absorbing systems, the chromophore of 4H-imidazoles was extended. The 4H-imidazo-[1,2-a]-pyridines, which are easily accessible by cyclization of 2-aminopyridines with bis-imidoylchlorides, show long wavelength absorptions up to 616 nm. Their reduction reversibly yields yellow, blue fluorescent 1-azaindolizines. In contrast to leucoforms reduction products show a high stability towards oxygen and could only forms of 4H-imidazoles, be reoxidized to their starting materials by oxidation agents, such as DDQ. (C) 2008 Elsevier Ltd. All rights reserved.