| 1374865-47-0

• 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
• CAS: 1374865-47-0
• 化学式: C₁₆H₁₀ClN₃O₂
• 分子量: 311.727
• InChiKey: CWEJYFWLJKRYNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.39
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  、 巯基乙酸 在 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以57%的产率得到2-(2-chloroquinoline-3-yl)-3-(3-nitrophenyl)thiazolidin-4-one
  参考文献：
  名称：

  Quinoline-based azetidinone and thiazolidinone analogues as antimicrobial and antituberculosis agents

  摘要：

  New azetidinone and thiazolidinone class of bioactive agents based on quinoline nucleus have been synthesized. 2-Chloroquinoline-3-carbaldehyde reacted with various substituted amine to form the corresponding Schiff base intermediates. We have derived final azetidinone and thiazolidinone analogues from Schiff bases using chloroacetyl chloride and 2-mercaptoacetic acid, respectively. The newly synthesized analogues were then examined for their antimicrobial activity against some bacterial and fungal strains as two gram -ve bacteria (Escherichia coli MTCC 739 and Pseudomonas aeruginosa MTCC 741), two gram +ve bacteria (Staphylococcus aureus MTCC 96 and Bacillus subtilis MTCC 430), two fungal species (Aspergillus niger MTCC 282 and Candida albicans MTCC 183) as well as against Mycobacterium tuberculosis strain H37Rv to develop a novel class of bioactive agents. The results of bioassay showed that some of the newly synthesized azetidinones and thiazolidinones emerged as lead molecules with excellent MIC (mg/mL) values against mentioned microorganisms compared to standard drugs. The structure of the final analogues has been confirmed on the basis of IR, H-1 NMR, C-13 NMR, and elemental analysis.

  DOI：

  10.1007/s00044-012-0061-7
• 作为产物：
  描述：

  苯胺 在 硫酸 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Quinoline-based azetidinone and thiazolidinone analogues as antimicrobial and antituberculosis agents

  摘要：

  New azetidinone and thiazolidinone class of bioactive agents based on quinoline nucleus have been synthesized. 2-Chloroquinoline-3-carbaldehyde reacted with various substituted amine to form the corresponding Schiff base intermediates. We have derived final azetidinone and thiazolidinone analogues from Schiff bases using chloroacetyl chloride and 2-mercaptoacetic acid, respectively. The newly synthesized analogues were then examined for their antimicrobial activity against some bacterial and fungal strains as two gram -ve bacteria (Escherichia coli MTCC 739 and Pseudomonas aeruginosa MTCC 741), two gram +ve bacteria (Staphylococcus aureus MTCC 96 and Bacillus subtilis MTCC 430), two fungal species (Aspergillus niger MTCC 282 and Candida albicans MTCC 183) as well as against Mycobacterium tuberculosis strain H37Rv to develop a novel class of bioactive agents. The results of bioassay showed that some of the newly synthesized azetidinones and thiazolidinones emerged as lead molecules with excellent MIC (mg/mL) values against mentioned microorganisms compared to standard drugs. The structure of the final analogues has been confirmed on the basis of IR, H-1 NMR, C-13 NMR, and elemental analysis.

  DOI：

  10.1007/s00044-012-0061-7

文献信息

• Synthesis of 2-azetidinones substituted quinoline derivative
  作者：Uday Mashelkar、Mukesh Jha、Beena Mashelkar

  DOI：10.2298/jsc120617081m

  日期：——

  Acetanilide is converted into 2-chloro-3-formyl quinoline by reacting with DMF-POCl3 at 80-90?C and then condensed with aromatic primary amines to give Schiff bases (3a-3c). These Schiff bases are then reacted with acid chlorides in the presence of base in toluene to give 1, 3, 4-substituted 2-azetidinones.

  乙酰苯胺在 80-90 摄氏度下与 DMF-POCl3 反应生成 2-氯-3-甲酰基喹啉，然后与芳香族伯胺缩合生成芳香族伯胺。 DMF-POCl3在 80-90 摄氏度下反应转化为 2-氯-3-甲酰基喹啉，然后与芳香族伯胺缩合得到 希夫碱（3a-3c）。然后这些希夫碱与酸氯化物反应 反应，得到 1、3、4-取代的 2-氮杂环丁酮。
• An efficient synthesis of strained thio-bridged compounds via Pd(0) catalyzed intramolecular Csp2(aryl)-Csp3(alkyl) cross dehydrohalogenative coupling reaction
  作者：Mayur I. Morja、Janki J. Patel、Prakashsingh M. Chauhan、Kishor H. Chikhalia

  DOI：10.1016/j.tet.2020.131348

  日期：2020.8

  An operationally simple and efficient strategy employing palladium(0) catalyst to construct a wide range of thiobridged compounds through intramolecular Csp2(aryl)-Csp3(alkyl) cross-dehydrohalogenative coupling reaction has been reported. This methodology proceeds smoothly through six-membered palladacycles and serving as a keystone for the generation of C–C bond to furnish thiobridged derivative in

  已经报道了一种使用钯（0）催化剂通过分子内Csp 2（芳基）-Csp 3（烷基）交叉脱卤化氢偶合反应构建各种硫桥化合物的操作简单有效的策略。该方法通过六元的palladacycles顺利进行，并成为生成C–C键的基石，从而以良好或优异的产率提供硫桥化合物。