3-cyano-4-phenylamino-1,2-dihydropyridin-2-one | 103607-70-1

• 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: 3-cyano-4-phenylamino-1,2-dihydropyridin-2-one
• 英文别名: 1-cyano-4-phenylamino-1,2-dihydropyrid-2-one；4-anilino-3-cyano-2-oxo-1,2-dihydropyridine；3-Cyano-4-phenylamino-2-pyridone；4-anilino-3-cyanopyridin-2-one；3-cyano-4-anilino-2-pyridone；2-Oxo-4-(phenylamino)-1,2-dihydropyridine-3-carbonitrile；4-anilino-2-oxo-1H-pyridine-3-carbonitrile
• CAS: 103607-70-1
• 化学式: C₁₂H₉N₃O
• mdl: MFCD00563978
• 分子量: 211.223
• InChiKey: NCENGPGNURJGGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  64.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-cyano-4-phenylamino-1,2-dihydropyridin-2-one 在 potassium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 6.0h， 以41%的产率得到4-phenylamino-1H-pyridin-2-one
  参考文献：
  名称：

  氨基胍和胍与 3-和 5-甲酰基-4-芳基氨基吡啶酮的反应

  摘要：

  脒腙是通过 4-arylamino-2-oxo-5-formyl-1,2-dihydropyridine-3-carbonitriles 和 4-arylamino-2-oxo-1,2-dihydropyridine-3-carbaldehydes 与氨基胍碳酸盐与目的是研究它们作为推定的 NO 供体的生物活性。研究了 5- 和 3-甲酰基吡啶酮与碳酸二胍的反应。发现了 4-芳基氨基-5-甲酰基-2-氧代-1,2-二氢吡啶-3-甲腈与氨基胍和胍的稳定复合物的形成。获得的脒腙具有抗炎、抗糖尿病和抗高血压活性。

  DOI：

  10.1007/s11172-010-0385-8
• 作为产物：
  描述：

  (Z)-3-anilino-2-cyanobut-2-enamide 在 氢氧化钾 、 水 作用下， 以 甲苯 为溶剂， 反应 13.0h， 生成 3-cyano-4-phenylamino-1,2-dihydropyridin-2-one
  参考文献：
  名称：

  Synthesis and hydrolytic cleavage of 1-aryl-5-cyano-6-(2-dimethylaminovinyl)-4-oxo(thioxo)-1,4-dihydropyrimidines

  摘要：

  1-Aryl-5-cyano-6-(2-dimethylaminovinyl)-4-oxo-1,4-dihydropyrimidines and their 4-thioxo analogs, which were prepared in three steps from cyanoacetamide and cyanothioacetamide, respectively, were subjected to hydrolysis. In aqueous AcOH, hydrolysis of N-(dimethylaminomethylene)-2-cyano-5-dimethylamino-2,4-pentadieneamide derivatives containing amino groups at position 3 afforded formylpyridones. The reaction of 2-cyano-3-dimethylaminothiocrotonamide with DMF dimethyl acetal gave rise to 3-cyano-4-dimethylamino-2-methylthiopyridine.

  DOI：

  10.1023/b:rucb.0000037857.07190.75

文献信息

• Synthesis and functionalization of 4-arylamino-2-pyridone derivatives
  作者：N. Z. Tugusheva、L. M. Alekseeva、A. S. Shashkov、V. V. Chernyshev、V. G. Granik

  DOI：10.1007/s11172-006-0443-4

  日期：2006.8

  New approaches to the synthesis of the previously unknown pyrimidine, 4-amino-2-pyridone, and 4-aminopyridine derivatives were developed based on the reactions of enaminoamides with dimethylformamide dimethyl acetal. New structural modifications of 4-amino-2-pyridone derivatives were performed. Numerous compounds of this type, which are of interest for biological studies, were prepared.

  根据烯酰胺与二甲基甲酰胺二甲基缩醛的反应，开发了合成以前未知的嘧啶、4-氨基-2-吡啶酮和 4-氨基吡啶衍生物的新方法。对 4-氨基-2-吡啶酮衍生物进行了新的结构改造。制备出了许多对生物研究有意义的此类化合物。
• ——
  作者：A. S. Ivanov、N. Z. Tugusheva、N. P. Solov"eva、V. G. Granik

  DOI：10.1023/a:1021636632164

  日期：——

  The reactions of 3-chloro-4-cyanobenzo[b][1,6]naphthyridine (4) with S-, C-, and N-nucleophiles afford stable sigma-adducts at position 10. In the base-catalyzed reactions of compound 4 with thiols, the resulting sigma-complexes are rearranged into sulfides 14a-c. Sulfides 14b,c undergo the Thorpe-Ziegler cyclization to give 1-aminobenzo[b]thieno[2,3-h][1,6]naphthyridine derivatives 15a,b. The reaction of naphthyridine 4 with aniline affords a mixture of sigma-adducts of the C-N and C-C types, while those with aliphatic amines yield 3-amino derivatives 17a-c. In the presence of H2O2, benzonaphthyridine 4 adds peroxycarboxylic acids to give compounds 8a,b. In alkaline medium, adduct 8a is rearranged into 4-aminopyridine-3-carbaldehyde derivative 10.
• Search for β-adrenoblockers in the 2-(2'-hydroxy-3'-isopropylaminopropoxy]-3-cyano-4-aminopyridine series
  作者：V. A. Azimov、V. G. Granik、S. I. Grizik、L. V. Ershov、N. I. Smetskaya、S. O. Yuzhakov、M. D. Mashkovskii、L. N. Yakhontov

  DOI：10.1007/bf00767827

  日期：1985.8
• ——
  作者：S. A. Ryndina、A. V. Kadushkin、N. P. Solov'eva、V. G. Granik

  DOI：10.1023/a:1017566212124

  日期：——
• AZIMOV, V. A.;GRANIK, V. G.;GRIZIK, S. I.;ERSHOV, L. V.;SMETSKAYA, N. I.;+, XIM.-FARMATS. ZH., 1985, 19, N 8, 947-952
  作者：AZIMOV, V. A.、GRANIK, V. G.、GRIZIK, S. I.、ERSHOV, L. V.、SMETSKAYA, N. I.、+

  DOI：——

  日期：——