Methyl 3-amino-5,6,7,8-tetrahydrothieno[2,3-b]quinoline-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: Methyl 3-amino-5,6,7,8-tetrahydrothieno[2,3-b]quinoline-2-carboxylate
• 化学式: C₁₃H₁₄N₂O₂S
• 分子量: 262.332
• InChiKey: GVZNNNWVSDWYFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 3-amino-5,6,7,8-tetrahydrothieno[2,3-b]quinoline-2-carboxylate 、 1-氰基乙酰-3,5-二甲基吡唑 以 甲苯 为溶剂， 反应 5.0h， 以70%的产率得到methyl 3-[(cyanoacetyl)amino]-5,6,7,8-tetrahydrothieno[2,3-b]quinoline-2-carboxylate
  参考文献：
  名称：

  Synthesis and Cyclizations of N-(Thieno[2,3-b]pyridin-3-yl)cyanoacetamides

  摘要：

  3-Aminothieno[2,3-b]pyridine-2-carboxylic acid esters readily reacted with 3,5-dimethyl-1-(cyanoacetyl)-1H-pyrazole to give previously unknown N-(thieno[2,3-b]pyridin-3-yl)cyanoacetamides. Reactions of the latter with 2-(arylmethylidene)malononitriles were nonselective, and mixtures of different heterocyclization products were generally formed. The cyclization of ethyl 4,6-dimethyl-3-[(cyanoacetyl)amino]thieno[2,3-b]pyridine-2-carboxylate afforded 2,4-dihydroxy-7,9-dimethylthieno[2,3-b : 4,5-b']dipyridine-3-carbonitrile whose tautomeric equilibrium was studied by DFT quantum chemical calculations. In silico analysis of biological activity of the synthesized compounds was performed.

  DOI：

  10.1134/s1070363219100062

文献信息

• Synthesis and Cyclizations of N-(Thieno[2,3-b]pyridin-3-yl)cyanoacetamides
  作者：E. A. Chigorina、A. V. Bespalov、V. V. Dotsenko

  DOI：10.1134/s1070363219100062

  日期：2019.10

  3-Aminothieno[2,3-b]pyridine-2-carboxylic acid esters readily reacted with 3,5-dimethyl-1-(cyanoacetyl)-1H-pyrazole to give previously unknown N-(thieno[2,3-b]pyridin-3-yl)cyanoacetamides. Reactions of the latter with 2-(arylmethylidene)malononitriles were nonselective, and mixtures of different heterocyclization products were generally formed. The cyclization of ethyl 4,6-dimethyl-3-[(cyanoacetyl)amino]thieno[2,3-b]pyridine-2-carboxylate afforded 2,4-dihydroxy-7,9-dimethylthieno[2,3-b : 4,5-b']dipyridine-3-carbonitrile whose tautomeric equilibrium was studied by DFT quantum chemical calculations. In silico analysis of biological activity of the synthesized compounds was performed.