1-(4-chlorophenyl)-1,2,4-triazolo[4,3-a]quinoxaline | 478189-64-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-chlorophenyl)-1,2,4-triazolo[4,3-a]quinoxaline
• 英文别名: 1-(4-Chlorophenyl)-[1,2,4]triazolo[4,3-A]quinoxaline；1-(4-chlorophenyl)-[1,2,4]triazolo[4,3-a]quinoxaline
• CAS: 478189-64-9
• 化学式: C₁₅H₉ClN₄
• 分子量: 280.716
• InChiKey: GPCOJJLGPHPFOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-1,2,4-triazolo[4,3-a]quinoxaline 、 苯乙炔 在 palladium 10% on activated carbon 、 potassium carbonate 作用下， 反应 12.0h， 以86%的产率得到1-(4-chlorophenyl)-4-(2-phenylethynyl)[1,2,4]triazolo[4,3-a]quinoxaline
  参考文献：
  名称：

  Pd/C-catalyzed, copper-free Sonogashira coupling: one-pot synthesis of 1-aryl-4-(2-phenylethynyl)[1,2,4]triazolo[4,3-a]quinoxalines in water

  摘要：

  Copper-free, Pd/C-catalyzed, one-pot reaction of 2,3-dichloroquinoxaline with hydrazine hydrate, bromine, phenylacetylene, and a variety of aldehydes provides an efficient and direct method for the preparation of 1-aryl-4-(2-phenylethynyl)[1,2,4]triazolo[4,3-a]quinoxalines in water at 70 A degrees C. This methodology involves the use of inexpensive reagents or catalysts, and thus permits a new and practical access to triazolo[4,3-a]quinoxalines.

  DOI：

  10.1007/s00706-012-0904-4
• 作为产物：
  描述：

  2-肼基喹喔啉 在 copper dichloride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.66h， 生成 1-(4-chlorophenyl)-1,2,4-triazolo[4,3-a]quinoxaline
  参考文献：
  名称：

  A convenient new synthesis of fused 1,2,4-triazoles: the oxidation of heterocyclic hydrazones using copper dichloride

  摘要：

  A series of 1,2,4-triazoles have been prepared by oxidative intramolecular cyclization of heterocyclic hydrazones with copper dichloride. General applicability of this simple transformation was confirmed by the synthesis of moderate to high yields of 1,2,4-triazolo[4,3-a]pyridines, 1,2,4-triazolo[4,3-a]pyrimidines, 1,2,4-triazolo[4,3-b]pyridazines, 1,2,4-triazolo[4,3-a]phthalazines, and 1,2,4-triazolo[4,3-a]quinoxalines. A 1,2,4-triazolo[4,3-e]purine-6,8(7H)-dione was obtained in a lower yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.111

文献信息

• A convenient new synthesis of fused 1,2,4-triazoles: the oxidation of heterocyclic hydrazones using copper dichloride
  作者：Michael Ciesielski、Daniela Pufky、Manfred Döring

  DOI：10.1016/j.tet.2005.01.111

  日期：2005.6

  A series of 1,2,4-triazoles have been prepared by oxidative intramolecular cyclization of heterocyclic hydrazones with copper dichloride. General applicability of this simple transformation was confirmed by the synthesis of moderate to high yields of 1,2,4-triazolo[4,3-a]pyridines, 1,2,4-triazolo[4,3-a]pyrimidines, 1,2,4-triazolo[4,3-b]pyridazines, 1,2,4-triazolo[4,3-a]phthalazines, and 1,2,4-triazolo[4,3-a]quinoxalines. A 1,2,4-triazolo[4,3-e]purine-6,8(7H)-dione was obtained in a lower yield. (c) 2005 Elsevier Ltd. All rights reserved.
• Pd/C-catalyzed, copper-free Sonogashira coupling: one-pot synthesis of 1-aryl-4-(2-phenylethynyl)[1,2,4]triazolo[4,3-a]quinoxalines in water
  作者：Mohammad Bakherad、Saeideh Jajarmi

  DOI：10.1007/s00706-012-0904-4

  日期：2013.6

  Copper-free, Pd/C-catalyzed, one-pot reaction of 2,3-dichloroquinoxaline with hydrazine hydrate, bromine, phenylacetylene, and a variety of aldehydes provides an efficient and direct method for the preparation of 1-aryl-4-(2-phenylethynyl)[1,2,4]triazolo[4,3-a]quinoxalines in water at 70 A degrees C. This methodology involves the use of inexpensive reagents or catalysts, and thus permits a new and practical access to triazolo[4,3-a]quinoxalines.