1-formyl-4-methoxyimidazo[1,2-a]quinoxaline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-formyl-4-methoxyimidazo[1,2-a]quinoxaline
• 英文别名: 4-Methoxyimidazo[1,2-a]quinoxaline-1-carbaldehyde
• 化学式: C₁₂H₉N₃O₂
• 分子量: 227.222
• InChiKey: ASMLFRRYZMCMDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯咪唑并[1,2-A]喹喔啉 在 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.25h， 生成 1-formyl-4-methoxyimidazo[1,2-a]quinoxaline
  参考文献：
  名称：

  Imidazo[1,2-a]quinoxalines: synthesis and cyclic nucleotide phosphodiesterase inhibitory activity

  摘要：

  A group of imidazo[1,2-a]quinoxalines have been synthesised from quinoxaline by condensation of an appropriate haloester or intramolecular cyclisation of a keto moiety on an intracyclic nitrogen atom. The reactivity of the heterocycle was explored through diverse reactions such as electrophilic substitution, lithiation and halogen-metal exchange to give access to a new series of derivatives. Confirmation of their structure was mainly performed by NMR, after careful assignment of the signals in comparison to previous attributions made on the parent imidazo[1,2-a]quinoxaline and discussion of available data in the literature. The cyclic nucleotide phosphodiesterase inhibitor activity of some of these derivatives has been assessed on isoenzymes type III and type IV. Compound 15, 4-(methylamino)imidazo[1,2-a]quinoxaline-2-carbonitrile, exhibited potent relaxant activity on smooth muscle, with a potency similar to the one measured with SCA 40, its structural analogue in the imidazo[1,2-a]pyrazine series. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01213-2

文献信息

• Metalation and halogen-metal exchange in the imidazo[1,2-<i>a</i>]quinoxaline series
  作者：Stéphanie Parra、Olivier Vitse、Véronique Bénézech、Carine Deleuze-Masquéfa、Guy Subra、Jacques Bompart、Roger Escale、Jean P. Chapat、Pierre A. Bonnet

  DOI：10.1002/jhet.5570380106

  日期：2001.1

  The n-butyllithium and lithium 2,2,6,6-tetramethylpiperidide metalation and the halogen-metal exchange of imidazo[1,2-a]quinoxaline derivatives followed by quenching with various electrophiles were studied. The reaction conditions have been optimized and various C1 substituted imidazo[1,2-a]quinoxalines were obtained in high yields.

  研究了正丁基锂和2,2,6,6-四甲基哌啶锂的金属化以及咪唑并[1,2- a ]喹喔啉衍生物的卤素-金属交换，然后用各种亲电试剂进行淬灭。优化了反应条件，并以高收率获得了各种C 1取代的咪唑并[1,2- a ]喹喔啉。
• Imidazo[1,2-a]quinoxalines: synthesis and cyclic nucleotide phosphodiesterase inhibitory activity
  作者：Stéphanie Parra、Florence Laurent、Guy Subra、Carine Deleuze-Masquefa、Veronique Benezech、Jean-Roch Fabreguettes、Jean-Pierre Vidal、Tristan Pocock、Keith Elliott、Roger Small、Roger Escale、Alain Michel、Jean-Pierre Chapat、Pierre-Antoine Bonnet

  DOI：10.1016/s0223-5234(01)01213-2

  日期：2001.3

  A group of imidazo[1,2-a]quinoxalines have been synthesised from quinoxaline by condensation of an appropriate haloester or intramolecular cyclisation of a keto moiety on an intracyclic nitrogen atom. The reactivity of the heterocycle was explored through diverse reactions such as electrophilic substitution, lithiation and halogen-metal exchange to give access to a new series of derivatives. Confirmation of their structure was mainly performed by NMR, after careful assignment of the signals in comparison to previous attributions made on the parent imidazo[1,2-a]quinoxaline and discussion of available data in the literature. The cyclic nucleotide phosphodiesterase inhibitor activity of some of these derivatives has been assessed on isoenzymes type III and type IV. Compound 15, 4-(methylamino)imidazo[1,2-a]quinoxaline-2-carbonitrile, exhibited potent relaxant activity on smooth muscle, with a potency similar to the one measured with SCA 40, its structural analogue in the imidazo[1,2-a]pyrazine series. (C) 2001 Editions scientifiques et medicales Elsevier SAS.