5-<(1,1'-biphenyl)-4-yl>oxazole-4-carboxaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-<(1,1'-biphenyl)-4-yl>oxazole-4-carboxaldehyde
• 英文别名: 5-(4-Phenylphenyl)-1,3-oxazole-4-carbaldehyde
• 化学式: C₁₆H₁₁NO₂
• 分子量: 249.269
• InChiKey: HZZPXQGIFSDZDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴-4-苯基乙酰苯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium azide 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5-<(1,1'-biphenyl)-4-yl>oxazole-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

文献信息

• The Vilsmeier cyclization of azides. Synthesis of oxazoles and vinyl azides from 2-azidoacetophenones
  作者：Vattoly J. Majo、Paramasivan T. Perumal

  DOI：10.1016/s0040-4039(97)01587-6

  日期：1997.9

  by an unprecedented Vilsmeier cyclization of 2-azidoacetophenones. One-pot synthesis of these oxazolecarboxaldehydes from 2-bromoacetophenones by dehaloazidation-Vilsmeier cyclization reaction sequence provided better yields. The treatment of 2-azidoacetophenones with Vilsmeier reagent (DMF/POCl3) at rt resulted in the exclusive formation of α-azido-β-chlorovinyl azides in moderate yields.

  5-芳基恶唑-4-羧醛的合成是通过空前的2-叠氮苯乙酮的Vilsmeier环化反应完成的。通过脱卤叠氮化-Vilsmeier环化反应序列从2-溴苯乙酮一锅合成这些恶唑甲醛，可提供更好的收率。在室温下用Vilsmeier试剂（DMF / POCl 3）处理2-叠氮苯乙酮，导致α-叠氮基-β-氯乙烯基叠氮化物以中等收率独家形成。
• A NOVEL ACCESS TO SOME 1,4-DICHLOROISOQUINOLINES FROM PHENACYL AZIDES
  作者：R. E. Chen、X. H. Zhou、W. H. Zhong、W. K. Su

  DOI：10.1080/00304940809458125

  日期：2008.12

  such as quinolines, indoles, quinazolines, pyridines, etc. In continuation of our previous work on exploring the use of bis(trichloromethy1) carbonate (BTC) in organic synthesis: we focused our research on the use of Vilsmeier salts derived from BTC and N,N-dimethylfomamide (DMF).5 Herein we describe a mild and efficient one-step synthesis of substituted 1,4-dichloroisoquinolines and 5-aryloxazole-4-carboxaldehydes

  最初用于活化芳香底物和羰基化合物 2 的甲酰化的 Vilsmeier-Haack 反应现已发展成为构建许多杂环化合物 3 如喹啉、吲哚、喹唑啉、吡啶等的强大合成工具。探索在有机合成中使用双（三氯甲基）碳酸酯 (BTC) 的工作：我们的研究重点是使用衍生自 BTC 和 N,N-二甲基甲酰胺 (DMF) 的 Vilsmeier 盐。 5 在此我们描述了一种温和高效的盐在 Vilsmeier 条件下从各种苯甲酰叠氮化物逐步合成取代的 1,4-二氯异喹啉和 5-芳基恶唑-4-甲醛。
• 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.