5,8-Dichloro-3-(4-chloropyridin-2-yl)-1,2,4-benzotriazine | 1426143-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 5,8-Dichloro-3-(4-chloropyridin-2-yl)-1,2,4-benzotriazine
• 英文别名: 5,8-dichloro-3-(4-chloropyridin-2-yl)-1,2,4-benzotriazine
• CAS: 1426143-03-4
• 化学式: C₁₂H₅Cl₃N₄
• 分子量: 311.558
• InChiKey: RRLGWLZTSBBMMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 吡啶 作用下， 以 二甲基亚砜 为溶剂， 生成 5,8-Dichloro-3-(4-chloropyridin-2-yl)-1,2,4-benzotriazine
  参考文献：
  名称：

  First synthesis of 5,8-dichloro-3-(2-pyridyl)benzo[e][1,2,4]triazines by reaction of 3,3,6,6-tetrachloro-1,2-cyclohexanedione with 2-pyridylamidrazones. Characterization of unexpected bishemiaminal intermediates

  摘要：

  A new approach to selected 1,2,4-benzotriazines has been developed. 3,3,6,6-Tetrachloro-1,2-cyclohexanedione reacted with 2-pyridylamidrazones to give unexpected isolable bishemiaminal intermediates instead of the corresponding ketodiazenes. Subsequent dehydration gave 5,5,8,8-tetrachloro-3-(2-pyridyl)-5,6,7,8-tetrahydrobenzo[e][1,2,4]triazines, which were converted into previously unknown 5,8-dichloro-3-(2-pyridyl)benzo[e][1,2,4]triazines by dehydrochlorination under basic conditions. Severe limitations of reactions between o-benzoquinones with amidrazones have been circumvented in this manner. This preparative process has also been adapted to a one-pot protocol. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.022

文献信息

• First synthesis of 5,8-dichloro-3-(2-pyridyl)benzo[e][1,2,4]triazines by reaction of 3,3,6,6-tetrachloro-1,2-cyclohexanedione with 2-pyridylamidrazones. Characterization of unexpected bishemiaminal intermediates
  作者：Antonio Guirado、José I. López Sánchez、Rubén Moreno、Jesús Gálvez

  DOI：10.1016/j.tetlet.2013.01.022

  日期：2013.3

  A new approach to selected 1,2,4-benzotriazines has been developed. 3,3,6,6-Tetrachloro-1,2-cyclohexanedione reacted with 2-pyridylamidrazones to give unexpected isolable bishemiaminal intermediates instead of the corresponding ketodiazenes. Subsequent dehydration gave 5,5,8,8-tetrachloro-3-(2-pyridyl)-5,6,7,8-tetrahydrobenzo[e][1,2,4]triazines, which were converted into previously unknown 5,8-dichloro-3-(2-pyridyl)benzo[e][1,2,4]triazines by dehydrochlorination under basic conditions. Severe limitations of reactions between o-benzoquinones with amidrazones have been circumvented in this manner. This preparative process has also been adapted to a one-pot protocol. (c) 2013 Elsevier Ltd. All rights reserved.