ethyl 2-amino-6-methyl-4-(4-nitrophenyl)-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylate | 1571152-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 2-amino-6-methyl-4-(4-nitrophenyl)-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylate
• 英文别名: ethyl 2-amino-6-methyl-4-(4-nitrophenyl)-5-oxo-4H-pyrano[3,2-c]quinoline-3-carboxylate
• CAS: 1571152-90-3
• 化学式: C₂₂H₁₉N₃O₆
• 分子量: 421.409
• InChiKey: IHNHZYXWGAOMBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-羟基-N-甲基-2-喹啉 、 乙基 2-氰基-3-(4-硝基苯基)丙烯酸酯 在 4-二甲氨基吡啶 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 ethyl 2-amino-6-methyl-4-(4-nitrophenyl)-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis and antibacterial activity of ethyl 2-amino-6-methyl-5-oxo-4-aryl-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylate

  摘要：

  The three-component reaction of 4-hydroxy-1-methyl-2(1H)-quinolinone, aromatic aldehydes and ethyl cyanoacetate was carried out in the presence of a catalytic amount of 4-dimethyl aminopyridine (DMAP) in aqueous ethanol. The reactions result in the formation of pyranoquinoline derivatives in excellent yields. Antibacterial activity has been evaluated against Gram positive and Gram negative bacteria for some of the synthesized compounds. The results indicated that these compounds are moderately effective against bacterial growth and their effectiveness is highest against Pseudomonas aeruginosa. (C) 2013 Sakineh Asghari. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.12.010

文献信息

• DBU Acetate Mediated: One-pot Multi Component Syntheses of Dihydropyrano[3,2-c]quinolones
  作者：Rajasekar Bhupathi、Bandi Madhu、B. Rama Devi、Ch. Venkata Ramana Reddy、P. K. Dubey

  DOI：10.1002/jhet.2506

  日期：2016.11

  Three‐component reaction involving condensation of 1‐methylquinoline‐2,4(1H,3H)‐dione(1), aromatic aldehydes (2a, 2b, 2c, 2d, 2e, 2f, 2g, 2h) and malononitrile/cyanoaceticester (3a, 3b) in(1,8‐diazabicyclo[5.4.0]‐undec‐7‐en‐8‐ium acetate)}[DBU][Ac] as task‐specific ionic liquid leading to the efficient synthesis of dihydropyrano[3,2‐c]quinolones (4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m

  三组分反应涉及1-甲基喹啉-2,4（1H，3H）-二酮（1），芳香醛（2a，2b，2c，2d，2e，2f，2g，2h）和丙二腈/氰基乙酸酯（3a，3b）1,8-diazabicyclo [5.4.0] -undec-7-en-8-醋酸盐}} [DBU] [Ac]中的盐作为任务特定的离子液体，可有效合成二氢吡喃[3 ，2-c]喹诺酮类（4a，4b，4c，4d，4e，4f，4g，描述了图4h，4i，4j，4k，4l，4m，4n，4o，4p）。该方法方便，温和，无需使用柱色谱法即可提供高收率的产品。
• Tandem Protocol for the Synthesis of Pyrano[3,2-<i>c</i>]quinolone Derivatives Using Taurine as a Green Bio-Organic Catalyst in Aqueous Medium
  作者：Kamlesh Saini、Ashok K. Raigar、Manju、Dinesh K. Jangid、Jaya Mathur、Surbhi Dhadda、Anjali Guleria

  DOI：10.1021/acs.joc.2c01403

  日期：2022.11.4