3-[(2-methoxyphenyl)ethynyl]quinoxaline-2-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-[(2-methoxyphenyl)ethynyl]quinoxaline-2-carbonitrile
• 英文别名: 3-[2-(2-Methoxyphenyl)ethynyl]quinoxaline-2-carbonitrile；3-[2-(2-methoxyphenyl)ethynyl]quinoxaline-2-carbonitrile
• 化学式: C₁₈H₁₁N₃O
• 分子量: 285.305
• InChiKey: SOFBKMZQDPLYFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(2-methoxyphenyl)ethynyl]quinoxaline-2-carbonitrile 在 氨 、 potassium carbonate 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以88%的产率得到(Z)-3-[2-amino-2-(2-methoxyphenyl)vinyl]quinoxaline-2-carbonitrile
  参考文献：
  名称：

  Nucleophilic cyclization of 3-alkynylquinoxaline-2-carbonitriles into pyrido[3,4-b]quinoxalines

  摘要：

  3-Alkynylquinoxaline-2-carbonitriles have been synthesized from 3-chloroquinoxaline-2-carbonitrile via the Sonogashira reaction. Treatment of 3-alkynylquinoxaline-2-carbonitriles with an alkylamine or ammonia has been shown to produce stable enamines, e.g., (Z)-3-(2-aryl-2-aminovinyl)quinoxaline-2-carbonitriles. Their base-induced cyclization gave the previously unknown pyrido[3,4-b]quinoxalin-1(2H)-imines or pyrido[3,4-b]quinoxalin-1-amines. 3-Alkynylquinoxaline-2-carbonitriles were directly transformed into pyrido[3,4-b]quinoxalin-1(2H)-imines by heating with an alkylamine and K2CO3 in DMF. The ionization constants, and absorption and fluorescent properties of the resulted pyrido[3,4-b] quinoxalin-1(2H)-imines were measured. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.005
• 作为产物：
  描述：

  2-乙炔基苯甲醚 、 2-氯喹喔啉-3-甲腈 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 2.33h， 以92%的产率得到3-[(2-methoxyphenyl)ethynyl]quinoxaline-2-carbonitrile
  参考文献：
  名称：

  Nucleophilic cyclization of 3-alkynylquinoxaline-2-carbonitriles into pyrido[3,4-b]quinoxalines

  摘要：

  3-Alkynylquinoxaline-2-carbonitriles have been synthesized from 3-chloroquinoxaline-2-carbonitrile via the Sonogashira reaction. Treatment of 3-alkynylquinoxaline-2-carbonitriles with an alkylamine or ammonia has been shown to produce stable enamines, e.g., (Z)-3-(2-aryl-2-aminovinyl)quinoxaline-2-carbonitriles. Their base-induced cyclization gave the previously unknown pyrido[3,4-b]quinoxalin-1(2H)-imines or pyrido[3,4-b]quinoxalin-1-amines. 3-Alkynylquinoxaline-2-carbonitriles were directly transformed into pyrido[3,4-b]quinoxalin-1(2H)-imines by heating with an alkylamine and K2CO3 in DMF. The ionization constants, and absorption and fluorescent properties of the resulted pyrido[3,4-b] quinoxalin-1(2H)-imines were measured. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.005

文献信息

• Nucleophilic cyclization of 3-alkynylquinoxaline-2-carbonitriles into pyrido[3,4-b]quinoxalines
  作者：Alexander S. Tyaglivy、Anna V. Gulevskaya、Alexander F. Pozharskii、Olga I. Askalepova

  DOI：10.1016/j.tet.2013.09.005

  日期：2013.11

  3-Alkynylquinoxaline-2-carbonitriles have been synthesized from 3-chloroquinoxaline-2-carbonitrile via the Sonogashira reaction. Treatment of 3-alkynylquinoxaline-2-carbonitriles with an alkylamine or ammonia has been shown to produce stable enamines, e.g., (Z)-3-(2-aryl-2-aminovinyl)quinoxaline-2-carbonitriles. Their base-induced cyclization gave the previously unknown pyrido[3,4-b]quinoxalin-1(2H)-imines or pyrido[3,4-b]quinoxalin-1-amines. 3-Alkynylquinoxaline-2-carbonitriles were directly transformed into pyrido[3,4-b]quinoxalin-1(2H)-imines by heating with an alkylamine and K2CO3 in DMF. The ionization constants, and absorption and fluorescent properties of the resulted pyrido[3,4-b] quinoxalin-1(2H)-imines were measured. (C) 2013 Elsevier Ltd. All rights reserved.