2-(benzoylamino)-3-cyanopyridine | 112084-93-2

• 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: 2-(benzoylamino)-3-cyanopyridine
• 英文别名: N-(3-cyanopyridin-2-yl)benzamide；2-benzoylaminonicotinonitrile
• CAS: 112084-93-2
• 化学式: C₁₃H₉N₃O
• 分子量: 223.234
• InChiKey: YAFUTJUVFMGMRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(benzoylamino)-3-cyanopyridine 在 五氯化磷 作用下， 以 环丁砜 为溶剂， 反应 12.0h， 以400 mg的产率得到4-chloro-2-phenylpyrido[2,3-d]pyrimidine
  参考文献：
  名称：

  Convenient and Practical One-Pot Synthesis of 4-Chloropyrimidines via a Novel Chloroimidate Annulation

  摘要：

  Reaction of aromatic or heteroaromatic 2-acyl(amino)nitriles with phosphorus pentachloride triggers a novel chloroimidate cyclization, leading directly to the corresponding annullated 4-chloropyrimidines in good to excellent yields. The reaction lends itself to the telescoped one-pot construction of 4-functionalized pyrimidines from the corresponding (hetero)aromatic 2-aminonitriles. For a pyrazolopyrimidine development intermediate, this reaction was scaled up to multikilogram scale with excellent results. A total of 10 examples with different substrates are provided. This one-pot reaction provides an attractive and sustainable alternative to the commonly used multistep methodology for this transformation.

  DOI：

  10.1021/op1002352
• 作为产物：
  描述：

  2-(苯甲酰氨基)吡啶-3-甲酰胺肟 在 盐酸 、 sodium hydroxide 、 硫酸 作用下， 以 氯仿 为溶剂， 反应 25.58h， 生成 2-(benzoylamino)-3-cyanopyridine
  参考文献：
  名称：

  Synthesis and transformations of some pyrido[2,3-d]pyrimidines

  摘要：

  DOI：

  10.1007/bf00809951

文献信息

• Pd-Catalyzed tandem reaction of <i>N</i>-(2-cyanoaryl)benzamides with arylboronic acids: synthesis of quinazolines
  作者：Jianghe Zhu、Yinlin Shao、Kun Hu、Linjun Qi、Tianxing Cheng、Jiuxi Chen

  DOI：10.1039/c8ob02421a

  日期：——

  The synthesis of 2,4-disubstituted quinazolines by a palladium-catalyzed reaction of arylboronic acids with N-(2-cyanoaryl)benzamides has been developed with moderate to excellent yields. The method shows good functional group tolerance. In particular, halogen and hydroxyl substituents, which are amenable for further synthetic elaborations, are well tolerated. Moreover, the present synthetic route

  已经开发了通过钯催化的芳基硼酸与N-（2-氰基芳基）苯甲酰胺的反应合成2,4-二取代的喹唑啉，其产率中等至优异。该方法显示出良好的官能团耐受性。特别是，对于进一步的合成修饰而言，卤素和羟基取代基是很好的耐受性。而且，本合成路线可以容易地按比例放大至克量而没有困难。该机制可能涉及亲核加成腈功能，形成亚胺中间体，然后分子内加成酰胺并脱水成喹唑啉环。
• KOCEVAR M.; KOLLER J.; STANOVNIK B.; TISLER M., MONATSH. CHEM., 118,(1987) N 3, 399-407
  作者：KOCEVAR M.、 KOLLER J.、 STANOVNIK B.、 TISLER M.

  DOI：——

  日期：——
• SUBSTITUTED BIARYL-4-CARBOXYLIC ACID ARYLAMIDE ANALOGUES AS CAPSAICIN RECEPTOR MODULATORS
  申请人：NEUROGEN CORPORATION

  公开号：EP1575918A2

  公开（公告）日：2005-09-21
• PROCESS FOR THE CATALYTIC DIRECTED CLEAVAGE OF AMIDE-CONTAINING COMPOUNDS
  申请人：Universiteit Antwerpen

  公开号：EP3362436B1

  公开（公告）日：2021-06-30
• [EN] SUBSTITUTED BIPHENYL-4-CARBOXYLIC ACID ARYLAMIDE ANALOGUES<br/>[FR] ANALOGUES D'ARYLAMIDE D'ACIDE BIPHENYL-4-CARBOXYLIQUE SUBSTITUES
  申请人：NEUROGEN CORP

  公开号：WO2004056774A2

  公开（公告）日：2004-07-08

  Substituted biphenyl-4-carboxylic acid arylamide analogues of the formula (I) capable of modulating receptor activity, are provided. Such ligands may be used to modulate receptor activity in vivo or in vitro, and are particularly useful in the treatment of pain and other conditions associated with receptor activation in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and methods for treating such disorders are provided, as are methods for using such ligands for receptor localization studies.