N-(3-hydroxypyridin-2-yl)benzamide | 69634-16-8

• 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: N-(3-hydroxypyridin-2-yl)benzamide
• CAS: 69634-16-8
• 化学式: C₁₂H₁₀N₂O₂
• mdl: MFCD08533174
• 分子量: 214.224
• InChiKey: RCERLEXNYYXISX-UHFFFAOYSA-N

物化性质

• 熔点：
  95-97 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  353.4±27.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-hydroxypyridin-2-yl)benzamide 在 Al³⁺ exchanged K₁₀ clay 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 16.0h， 以89%的产率得到2-phenyl[1,3]oxazolo[4,5-b]pyridine
  参考文献：
  名称：

  A green route for the synthesis of 2-substituted benzoxazole derivatives catalyzed by Al3+-exchanged K10 clay

  摘要：

  A new, simple, and efficient protocol is developed for the synthesis of 2-substituted benzoxazole derivatives through N-C-O bond formation using Al3+-exchanged K10 clay (Al3+-K10) as catalyst. A wide range of benzoxazole derivatives are synthesized in high yields without affecting many functional groups. Hot filtration experiments showed the absence of metal leaching and catalyst can be reused for five times with only a slight decrease in yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.039
• 作为产物：
  描述：

  2-氨基-3-羟基吡啶 在 氢氧化钾 、 碳酸氢钠 作用下， 生成 N-(3-hydroxypyridin-2-yl)benzamide
  参考文献：
  名称：

  Heterocyclic Studies. VII. The Preparation and Reactions of 2-Amino-5-hydroxypyridines; the Formation of an Azaquinone¹

  摘要：

  DOI：

  10.1021/ja01531a047

文献信息

• A Cross-Coupling Approach to Amide Bond Formation from Esters
  作者：Taoufik Ben Halima、Jaya Kishore Vandavasi、Mohanad Shkoor、Stephen G. Newman

  DOI：10.1021/acscatal.7b00245

  日期：2017.3.3

  A palladium-catalyzed cross-coupling between aryl esters and anilines is reported, enabling access to diverse amides. The reaction takes place via activation of the C–O bond by oxidative addition with a Pd–NHC complex, which enables the use of relatively non-nucleophilic anilines that otherwise require stoichiometric activation with strong bases in order to react. High yields of aromatic, aliphatic

  据报道，钯催化的芳基酯和苯胺之间的交叉偶联，使得能够获得各种酰胺。反应是通过Pd-NHC络合物的氧化加成激活C-O键来进行的，这使得能够使用相对非亲核的苯胺，否则需要化学计量的活化才能使强碱发生反应。获得高产率的芳族，脂族和杂环产物。在存在和不存在催化剂的情况下评估了一系列活化酯，这表明催化方法大大增加了在不存在苛刻碱的情况下可用于酰胺键形成的亲电试剂的类型。
• Synthesis of Some N¹-(3-Hydroxy-2-pyridyl)benzamides
  作者：A. Mobinikhaledi、N. Foroughifar、M. Fallah

  DOI：10.1080/10426500500270032

  日期：2006.4.1

  11 , 12 However, synthesis and especially biological activity of N-(3-hydroxy-2-pyridyl)benzamides were not studied well. Owing to the versatility of benzamides we have extended the reaction of 2-amino-3-pyridinol with different carboxylic acid chlorides in order to preparation of some new benzamide derivatives containing a hydroxypyridyl ring.

  苯并恶唑具有多种生物学特性，例如抗组胺、抗蠕虫、抗真菌和抗菌活性，因此受到特别关注。1, 2, 3, 4, 5, 6, 7, 8, 9, 10 苯甲酰胺衍生物作为苯并恶唑的可能代谢物，显示出多种类型的生物活性。11, 12 通过在弱碱性溶液下用羧酸氯化物处理 2-氨基苯酚合成了一些 N-(2-羟基苯基)-苯甲酰胺，与苯基乙酰胺和呋喃酰胺相比，它们显示出显着的活性。11, 12 然而，N-(3-羟基-2-吡啶基)苯甲酰胺的合成，尤其是生物活性没有得到很好的研究。
• Microwave-assisted chemoselective transamidation of secondary amides by selective N–C(O) bond cleavage under catalyst, additive and solvent-free conditions
  作者：Vishal Singh、Khushbu Rajput、Ankush Mishra、Sundaram Singh、Vandana Srivastava

  DOI：10.1039/d3cc04128j

  日期：——

  A microwave-assisted, highly chemoselective protocol has been developed for the transamidation of tert-butyloxycarbonyl (Boc) activated secondary carboxamides with amines. Under non-conventional microwave techniques, the reactions were achieved under catalyst, additive, promoter and solvent-free conditions. The transamidation of a structurally diverse set of amides and amines was accomplished in good

  已经开发出一种微波辅助、高度化学选择性的方案，用于叔丁氧基羰基 (Boc) 活化的仲酰胺与胺的转酰胺基作用。在非常规微波技术下，反应在催化剂、添加剂、促进剂和无溶剂条件下完成。一组结构多样的酰胺和胺的转酰胺基化反应以良好至优异的产率完成。该方法的显着特点包括操作简单、底物范围广泛、官能团耐受性、实用性和可扩展性。