2-oxo-6-(3-pyridinyl)-4-[4-(2-pyridinyl)-1-piperazinyl]-2H-pyran-3-carbonitrile | 518308-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-oxo-6-(3-pyridinyl)-4-[4-(2-pyridinyl)-1-piperazinyl]-2H-pyran-3-carbonitrile
• 英文别名: 2-oxo-6-pyridin-3-yl-4-(4-pyridin-2-ylpiperazin-1-yl)pyran-3-carbonitrile
• CAS: 518308-93-5
• 化学式: C₂₀H₁₇N₅O₂
• 分子量: 359.387
• InChiKey: CKOBNZCBNTZETE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-oxo-6-(3-pyridinyl)-4-[4-(2-pyridinyl)-1-piperazinyl]-2H-pyran-3-carbonitrile 在 吡啶 、 ammonium carbonate 作用下， 以46%的产率得到4-(4-pyridin-2-yl-piperazin-1-yl)-[2,3']bipyridin-6-ylamine
  参考文献：
  名称：

  Synthesis of Aminonicotinonitriles and Diaminopyridines through Base-Catalyzed Ring Transformation of 2H-Pyran-2-ones

  摘要：

  An efficient and convenient synthesis of 2-amino-6-aryl-4-methylsulfanylnicotinonitriles (2), 2-amino-6-aryl-4-substituted-aminonicotinonitriles (4), and 2-amino-6-aryl-4-substituted-aminopyridines (6) has been delineated and illustrated through base-catalyzed ring transformation of 6-aryl-3-cyano-4-methylsulfanyl/substituted-amino-2H-pyran-2-ones (1, 3, and 5) with cyanamide and ammonium carbonate separately.

  DOI：

  10.1021/jo0204496
• 作为产物：
  描述：

  4-methylsulfanyl-2-oxo-6-pyridin-3-yl-2H-pyran-3-carbonitrile 、 1-(2-吡啶基)哌嗪 以63%的产率得到2-oxo-6-(3-pyridinyl)-4-[4-(2-pyridinyl)-1-piperazinyl]-2H-pyran-3-carbonitrile
  参考文献：
  名称：

  Synthesis of Aminonicotinonitriles and Diaminopyridines through Base-Catalyzed Ring Transformation of 2H-Pyran-2-ones

  摘要：

  An efficient and convenient synthesis of 2-amino-6-aryl-4-methylsulfanylnicotinonitriles (2), 2-amino-6-aryl-4-substituted-aminonicotinonitriles (4), and 2-amino-6-aryl-4-substituted-aminopyridines (6) has been delineated and illustrated through base-catalyzed ring transformation of 6-aryl-3-cyano-4-methylsulfanyl/substituted-amino-2H-pyran-2-ones (1, 3, and 5) with cyanamide and ammonium carbonate separately.

  DOI：

  10.1021/jo0204496

文献信息

• Carbanion induced synthesis of annulated unsymmetrical biaryls through ring transformation of 2H-pyran-2-oneCentral Drug Research Institute communication no. 6207
  作者：Vishnu Ji Ram、Nidhi Agarwal、Abhishek S. Saxena、Ashoke Sharon、Prakas R. Maulik

  DOI：10.1039/b203544h

  日期：2002.6.7

  An innovative and convenient one-pot synthesis of unsymmetrical macrocyclic biaryls (3, 5 and 8), dibenzo[a,c]cycloheptenes (10), 3,4-dihydro-2(1H)-naphthones (15), tetrahydroisoquinolines (18), dihydro-1H-isothiochromenes (20), benzo[c]thiochromenes (22) and 2,3-dihydro-1-benzothiophenes (24) is described. These compounds are obtained through base-catalyzed ring transformation reactions of suitably functionalized 2H-pyran-2-ones (1,6) by a carbanion, generated from cycloalkanone (2,4,7), benzosuberone (9), cyclohexanedione monoketal (12), 4-piperidone (17), tetrahydrothiopyran-4-one (19), thiochroman-4-one (21) or tetrahydrothiophene-3-one (23).

  创新而便捷地一步合成非对称大环双芳酯（3、5 和 8）、二苯并[a,c]环庚烯（10）、3,4-二氢-2(1H)-萘酮（15）、四氢异喹啉（18）、二氢-1H-异硫代苯（20）、苯并[c]硫代苯（22）和 2,3-二氢-1-苯并[c]环庚烯（22）、本研究描述了通过碱-化学反应获得的四氢异喹啉 (18)、二氢-1H-异硫代苯 (20)、苯并[c]硫代苯 (22) 和 2,3-二氢-1-苯并噻吩 (24)。这些化合物是通过环烷酮（2,4,7）、苯并环戊酮（9）、环己二酮单酮（12）、4-哌啶酮（17）、四氢噻喃-4-酮（19）、硫代苯并二氢吡喃-4-酮（21）或四氢噻吩-3-酮（23）中的一个碳离子对适当官能化的 2H-吡喃-2-酮（1,6）进行碱催化环转化反应而得到的。
• Synthesis of Aminonicotinonitriles and Diaminopyridines through Base-Catalyzed Ring Transformation of 2<i>H</i>-Pyran-2-ones
  作者：Farhanullah、Nidhi Agarwal、Atul Goel、Vishnu Ji Ram

  DOI：10.1021/jo0204496

  日期：2003.4.1

  An efficient and convenient synthesis of 2-amino-6-aryl-4-methylsulfanylnicotinonitriles (2), 2-amino-6-aryl-4-substituted-aminonicotinonitriles (4), and 2-amino-6-aryl-4-substituted-aminopyridines (6) has been delineated and illustrated through base-catalyzed ring transformation of 6-aryl-3-cyano-4-methylsulfanyl/substituted-amino-2H-pyran-2-ones (1, 3, and 5) with cyanamide and ammonium carbonate separately.