5-amino-7-(2-hydroxyphenyl)-8-nitro-1,2,3,7-tetrahydroimidazo[1,2-a]pyridine-6-carbonitrile | 1446874-48-1

• 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: 5-amino-7-(2-hydroxyphenyl)-8-nitro-1,2,3,7-tetrahydroimidazo[1,2-a]pyridine-6-carbonitrile
• 英文别名: 5-Amino-7-(2-hydroxyphenyl)-8-nitro-1,2,3,7-tetrahydroimidazo[1,2-a]pyridine-6-carbonitrile
• CAS: 1446874-48-1
• 化学式: C₁₄H₁₃N₅O₃
• 分子量: 299.289
• InChiKey: QHAMPXSTUUSQNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-cyano-2-iminocoumarin 、 乙二胺 、 1,1-双(甲硫基)-2-亚硝基乙烯 以 乙醇 为溶剂， 反应 5.0h， 以83%的产率得到5-amino-7-(2-hydroxyphenyl)-8-nitro-1,2,3,7-tetrahydroimidazo[1,2-a]pyridine-6-carbonitrile
  参考文献：
  名称：

  Recyclization of 2-Iminochromenes via Ketene Aminal Intermediates: One-Pot, Three-Component Reaction for Synthesis of 1,4-Dihydropyridines-fused-1,3-diazaheterocycles

  摘要：

  An efficient, one-pot synthesis of 4-aryl-1,4-dihyropyrido[1,2-a]-fused-1,3-diazaheterocycles by three-component reaction of 1,n-diamine, nitroketene dithioacetal (1,1-di(methylthio)-2-nitroethene), and 2-iminochromenes in EtOH is reported. This new protocol has the advantages of good yields, short reaction times, and convenient operation. The structures were corroborated spectroscopically (infrared, H-1 and C-13 NMR, and electron impact-mass spectrometry) and by elemental analyses. A plausible mechanism for this type of recyclization is proposed. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.714040

文献信息

• Synthesis of imidazo[1,2-a]pyridine, pyrido[1,2-a]pyrimidine, and 3-cyanocoumarin
  作者：Mohammad Bayat、Monireh Rezaei

  DOI：10.1007/s00706-017-2033-6

  日期：2017.12

  AbstractA one-pot protocol for the synthesis of tetrahydroimidazo[1,2-a]pyridines, tetrahydropyrido[1,2-a]pyrimidines, and 3-cyanocoumarine derivatives was developed by condensing of various 1,n-diamines, 1,1-bis(methylthio)-2-nitroethene, substituted salicylaldehyde, and malononitrile or alkyl cyanoacetate at reflux condition in ethanol. Graphical abstract

  摘要通过缩合各种1，n-二胺，1,1-开发了一种一锅法合成四氢咪唑并[1,2- a ]吡啶，四氢吡啶并[1,2- a ]嘧啶和3-氰基香豆素衍生物的方法。双（甲硫基）-2-硝基乙烯，取代的水杨醛和丙二腈或氰基乙酸烷基酯在乙醇中回流的条件。 图形概要
• Recyclization of 2-Iminochromenes via Ketene Aminal Intermediates: One-Pot, Three-Component Reaction for Synthesis of 1,4-Dihydropyridines-fused-1,3-diazaheterocycles
  作者：Abdolali Alizadeh、Rashid Ghanbaripour、Long-Guan Zhu

  DOI：10.1080/00397911.2012.714040

  日期：2013.10.2

  An efficient, one-pot synthesis of 4-aryl-1,4-dihyropyrido[1,2-a]-fused-1,3-diazaheterocycles by three-component reaction of 1,n-diamine, nitroketene dithioacetal (1,1-di(methylthio)-2-nitroethene), and 2-iminochromenes in EtOH is reported. This new protocol has the advantages of good yields, short reaction times, and convenient operation. The structures were corroborated spectroscopically (infrared, H-1 and C-13 NMR, and electron impact-mass spectrometry) and by elemental analyses. A plausible mechanism for this type of recyclization is proposed. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.