2-azido-N-(2-ethylphenyl)acetamide | 215320-58-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-azido-N-(2-ethylphenyl)acetamide
• CAS: 215320-58-4
• 化学式: C₁₀H₁₂N₄O
• 分子量: 204.231
• InChiKey: LVDGITIFJLTIOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甲酰胺 、 2-azido-N-(2-ethylphenyl)acetamide 在 三氯氧磷 作用下， 以36%的产率得到5-chloro-2-(dimethylamino)-1-(2-ethylphenyl)-1H-imidazole-4-carboxaldehyde
  参考文献：
  名称：

  Intramolecular Cyclization of Azides by Iminium Species. A Novel Method for the Construction of Nitrogen Heterocycles under Vilsmeier Conditions

  摘要：

  An unprecedented attack of the azide functionality by iminium species, generated in situ under Vilsmeier conditions, provided a novel route for the construction of nitrogen heterocycles. Thus, the treatment of 2-azidoacetophenones with Vilsmeier reagent under reflux conditions gave 5-aryloxazole-4-carboxaldehydes. One-pot synthesis of oxazole carboxaldehydes from 2-bromoacetophenones by dehaloazidation-Vilsmeier cyclization reaction sequence provided better yields. The susceptibility of the carbonyl group to undergo chloroformylation at room temperature without affecting the azide function was exploited to provide an attractive scheme for the synthesis of alpha-azido-beta-chlorovinyl azides from phenacyl azides. The synthesis of a series of N-aryl 5-chloro-2-(dimethylamino)imidazole-4-carboxaldehydes was accomplished by the Vilsmeier cyclization of N-aryl-2-azidoacetamides. The possible mechanisms for the reactions are also discussed.

  DOI：

  10.1021/jo971745z
• 作为产物：
  描述：

  2-氯-n-(2-乙基苯基)乙酰胺 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-azido-N-(2-ethylphenyl)acetamide
  参考文献：
  名称：

  Intramolecular Cyclization of Azides by Iminium Species. A Novel Method for the Construction of Nitrogen Heterocycles under Vilsmeier Conditions

  摘要：

  An unprecedented attack of the azide functionality by iminium species, generated in situ under Vilsmeier conditions, provided a novel route for the construction of nitrogen heterocycles. Thus, the treatment of 2-azidoacetophenones with Vilsmeier reagent under reflux conditions gave 5-aryloxazole-4-carboxaldehydes. One-pot synthesis of oxazole carboxaldehydes from 2-bromoacetophenones by dehaloazidation-Vilsmeier cyclization reaction sequence provided better yields. The susceptibility of the carbonyl group to undergo chloroformylation at room temperature without affecting the azide function was exploited to provide an attractive scheme for the synthesis of alpha-azido-beta-chlorovinyl azides from phenacyl azides. The synthesis of a series of N-aryl 5-chloro-2-(dimethylamino)imidazole-4-carboxaldehydes was accomplished by the Vilsmeier cyclization of N-aryl-2-azidoacetamides. The possible mechanisms for the reactions are also discussed.

  DOI：

  10.1021/jo971745z

文献信息

• Intramolecular Cyclization of Azides by Iminium Species. A Novel Method for the Construction of Nitrogen Heterocycles under Vilsmeier Conditions
  作者：Vattoly J. Majo、Paramasivan T. Perumal

  DOI：10.1021/jo971745z

  日期：1998.10.1

  An unprecedented attack of the azide functionality by iminium species, generated in situ under Vilsmeier conditions, provided a novel route for the construction of nitrogen heterocycles. Thus, the treatment of 2-azidoacetophenones with Vilsmeier reagent under reflux conditions gave 5-aryloxazole-4-carboxaldehydes. One-pot synthesis of oxazole carboxaldehydes from 2-bromoacetophenones by dehaloazidation-Vilsmeier cyclization reaction sequence provided better yields. The susceptibility of the carbonyl group to undergo chloroformylation at room temperature without affecting the azide function was exploited to provide an attractive scheme for the synthesis of alpha-azido-beta-chlorovinyl azides from phenacyl azides. The synthesis of a series of N-aryl 5-chloro-2-(dimethylamino)imidazole-4-carboxaldehydes was accomplished by the Vilsmeier cyclization of N-aryl-2-azidoacetamides. The possible mechanisms for the reactions are also discussed.