6-dimethylamino-2-oxo-1,2-dihydro-pyridine-3-carbonitrile | 64792-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-dimethylamino-2-oxo-1,2-dihydro-pyridine-3-carbonitrile
• 英文别名: Otohynunjoienn-uhfffaoysa-；6-(dimethylamino)-2-oxo-1H-pyridine-3-carbonitrile
• CAS: 64792-43-4
• 化学式: C₈H₉N₃O
• 分子量: 163.179
• InChiKey: OTOHYNUNJOIENN-UHFFFAOYSA-N

物化性质

• 熔点：
  282-283 °C(Solv: ethanol (64-17-5))
• 沸点：
  312.2±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-2-Cyano-5,5-bis-dimethylamino-penta-2,4-dienoic acid amide 反应 0.5h， 以93%的产率得到6-dimethylamino-2-oxo-1,2-dihydro-pyridine-3-carbonitrile
  参考文献：
  名称：

  Orthoamide. LI. Push-Pull-Butadiene und Heterocyclen aus CH2-aciden Verbindungen und Orthoamiden von Alkincarbons�uren

  摘要：

  The acetylides 4b, 4f react with N,N,N',N',N ",N "-hexamethylguanidiniumchloride (5) to give the orthoamides 6b, 6f, resp. From CH2-acidic compounds and the orthoamides 6a, c, e can be obtained the push-pull-substituted butadienes 8a-8aj. The 2,3,5-trimethyl-thiadiazolium salt 9 does not condense with 6e, as other CH2-acidic compounds do, instead the vinylogous guanidinium salt 10a is produced. On healing, the ketenaminals 8d, aa cyclize to give the pyridone-carbonitriles 11a, b, resp. From di-amino-coumarins 12 and the ortho-carboxylic acid amideacetals 13a, b and the ketenaminal 16 resp., the amidines 14a-c and the heterocyclic compounds 15a-c resp., are formed. The enamines 17a-c, 19a, b react with the orthoamides 6a-f to give the pyridine derivatives 18a-l, 20a-h and 21a, b, resp. Analogously, from 6-amino-uracil 22 and 6a, b, e, fare formed the pure 7-dimethylaminopyrido[2,3-d] pyrimidines 23a, b or mixtures of compounds 23c, d and the isomeric 4-dimethylamino-pyrido[2,3d]pyrimidines 24a, b resp., which can be separated via their salts 25a,b/26a,b. The heterocyclic compounds 30a-d, 32a,16 can be prepared from the pyrazole derivatives 28, 31 resp. and the orthoamides 6a-f.

  DOI：

  10.1002/prac.19983400503

文献信息

• Reaction of diendiaminodiketones with nucleophilic reagents. Synthesis of 2-pyridone and 2-pyridinethione derivatives
  作者：A. K. Shanazarov、V. G. Granik

  DOI：10.1007/bf00762005

  日期：1987.3
• SHANAZAROV A. K.; GRANIK V. G., XIMIYA GETEROTSIKL. SOED.,(1987) N 3, 423-424
  作者：SHANAZAROV A. K.、 GRANIK V. G.

  DOI：——

  日期：——
• Orthoamide. LI. Push-Pull-Butadiene und Heterocyclen aus CH2-aciden Verbindungen und Orthoamiden von Alkincarbons�uren
  作者：Willi Kantlehner、Markus Vettel、Hansj�rg Lehmann、Kai Edelmann、R�diger Stieglitz、Ivo C. Ivanov

  DOI：10.1002/prac.19983400503

  日期：——

  The acetylides 4b, 4f react with N,N,N',N',N ",N "-hexamethylguanidiniumchloride (5) to give the orthoamides 6b, 6f, resp. From CH2-acidic compounds and the orthoamides 6a, c, e can be obtained the push-pull-substituted butadienes 8a-8aj. The 2,3,5-trimethyl-thiadiazolium salt 9 does not condense with 6e, as other CH2-acidic compounds do, instead the vinylogous guanidinium salt 10a is produced. On healing, the ketenaminals 8d, aa cyclize to give the pyridone-carbonitriles 11a, b, resp. From di-amino-coumarins 12 and the ortho-carboxylic acid amideacetals 13a, b and the ketenaminal 16 resp., the amidines 14a-c and the heterocyclic compounds 15a-c resp., are formed. The enamines 17a-c, 19a, b react with the orthoamides 6a-f to give the pyridine derivatives 18a-l, 20a-h and 21a, b, resp. Analogously, from 6-amino-uracil 22 and 6a, b, e, fare formed the pure 7-dimethylaminopyrido[2,3-d] pyrimidines 23a, b or mixtures of compounds 23c, d and the isomeric 4-dimethylamino-pyrido[2,3d]pyrimidines 24a, b resp., which can be separated via their salts 25a,b/26a,b. The heterocyclic compounds 30a-d, 32a,16 can be prepared from the pyrazole derivatives 28, 31 resp. and the orthoamides 6a-f.