2-imino-5-hydroxymethyl-8-methyl-2H-pyrano[2,3-c]pyridine-3-carboxamide | 778590-49-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: 2-imino-5-hydroxymethyl-8-methyl-2H-pyrano[2,3-c]pyridine-3-carboxamide
• 英文别名: 5-Hydroxymethyl-2-imino-8-methyl-2h-pyrano[2,3-c]pyridine-3-carboxamide；5-(hydroxymethyl)-2-imino-8-methylpyrano[2,3-c]pyridine-3-carboxamide
• CAS: 778590-49-1
• 化学式: C₁₁H₁₁N₃O₃
• 分子量: 233.227
• InChiKey: XKQZXFDOHBWWMF-UHFFFAOYSA-N

物化性质

• 熔点：
  198-199 °C(Solv: ethanol (64-17-5))
• 沸点：
  523.0±60.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-imino-5-hydroxymethyl-8-methyl-2H-pyrano[2,3-c]pyridine-3-carboxamide 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.5h， 以105 mg的产率得到5-(hydroxymethyl)-8-methyl-2-oxo-2H-pyrano[2,3-c]pyridine-3-carboxamide
  参考文献：
  名称：

  Diastereoselective Synthesis of Methanopyridoxazocinones

  摘要：

  Two approaches to the synthesis of oxygen-bridged tetrahydropyridones have been developed. In the first approach, substituted pyrido[4,3-g][1,3]oxazocines derivatives were prepared by diastereoselective one-pot reactions of substituted 7-azacoumarins with enolizable ketones and non-bulky primary amines. In the second one, 3-amido-7-azacoumarins were reacted with enolizable ketones in the presence of a base to form diastereomerically pure pyrido[4,3-g][1,3]oxazocines.

  DOI：

  10.1055/s-0034-1379182
• 作为产物：
  描述：

  吡哆醛盐酸盐 、 氰乙酰胺 在 哌啶 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以74%的产率得到2-imino-5-hydroxymethyl-8-methyl-2H-pyrano[2,3-c]pyridine-3-carboxamide
  参考文献：
  名称：

  取代的3-（5-氨基-[1,3,4]噻二唑-2-基）-2 H-吡喃并[2,3 - c ]吡啶-2-酮的合成

  摘要：

  开发了有效的两步合成新型3-（5-氨基-[1,3,4]噻二唑-2-基）-2 H-吡喃并[2,3 - c ]吡啶-2-酮。第一步，通过吡pyr醛盐酸盐与氰基乙酰胺的Knoevenagel缩合制备新的2 H-吡喃并[2,3 - c ]吡啶-3-甲酰胺5。在第二步中，羧酰胺5与一系列N 4取代的硫代氨基脲的反应以高收率产生了35种离散化合物8 {1-35}的库。讨论了导致这些产物的分子间再循环机理。

  DOI：

  10.1002/jhet.5570410407

文献信息

• Convenient Synthesis of Substituted 5‐(Hydroxymethyl)‐8‐methyl‐3‐(4‐phenylquinazolin‐2‐yl)‐2<i>H</i>‐pyrano[2,3‐<i>c</i>]pyridin‐2‐ones
  作者：Irina O. Zhuravel、Sergiy M. Kovalenko、Alexandre V. Ivachtchenko、Valentin P. Chernykh、Pavlo E. Shinkarenko

  DOI：10.1081/scc-200061638

  日期：2005.6.1

  Interaction of 2-imino-2H-pyrano[2,3-c] pyridin-3-carboxamide with substituted 2-aminobenzophenones proceeds via recyclization mechanism leading to substituted 3-(4-arylquinazolyn-2-yl)-2H-pyrano[2,3-c]pyridin-2-ones. Their reaction with acetic anhydride affords the O-acylation products.
• Synthesis of substituted 3-(5-amino-[1,3,4]thiadiazol-2-yl)-2<i>H</i>-pyrano[2,3-<i>c</i>]pyridin-2-ones
  作者：Irina O. Zhuravel'、Sergiy M. Kovalenko、Alexandre V. Ivachtchenko、Valentin P. Chernykh、Pavlo E. Shinkarenko

  DOI：10.1002/jhet.5570410407

  日期：2004.7

  An efficient two-step synthesis of novel 3-(5-amino-[1,3,4]thiadiazol-2-yl)-2H-pyrano[2,3-c]pyridine-2-ones was developed. In the first step, a new 2H-pyrano[2,3-c]pyridine-3-carboxamide 5 was prepared by Knoevenagel condensation of pyridoxal hydrochloride with cyanoacetamide. In the second step, the reaction of carboxamide 5 with a series of N4-substituted thiosemicarbazides yielded a library of 35

  开发了有效的两步合成新型3-（5-氨基-[1,3,4]噻二唑-2-基）-2 H-吡喃并[2,3 - c ]吡啶-2-酮。第一步，通过吡pyr醛盐酸盐与氰基乙酰胺的Knoevenagel缩合制备新的2 H-吡喃并[2,3 - c ]吡啶-3-甲酰胺5。在第二步中，羧酰胺5与一系列N 4取代的硫代氨基脲的反应以高收率产生了35种离散化合物8 1-35}的库。讨论了导致这些产物的分子间再循环机理。
• Diastereoselective Synthesis of Methanopyridoxazocinones
  作者：Siva Panda、C. Hall、Oleksandr Detistov、Peter Steel、Abdullah Asiri、Alan Katritzky

  DOI：10.1055/s-0034-1379182

  日期：——

  Two approaches to the synthesis of oxygen-bridged tetrahydropyridones have been developed. In the first approach, substituted pyrido[4,3-g][1,3]oxazocines derivatives were prepared by diastereoselective one-pot reactions of substituted 7-azacoumarins with enolizable ketones and non-bulky primary amines. In the second one, 3-amido-7-azacoumarins were reacted with enolizable ketones in the presence of a base to form diastereomerically pure pyrido[4,3-g][1,3]oxazocines.