3,9-dichloro-[1,2,3]triazolo[1,5-a]quinoline | 1165569-14-1

• 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: 3,9-dichloro-[1,2,3]triazolo[1,5-a]quinoline
• 英文别名: 3,9-Dichlorotriazolo[1,5-a]quinoline；3,9-dichlorotriazolo[1,5-a]quinoline
• CAS: 1165569-14-1
• 化学式: C₁₀H₅Cl₂N₃
• 分子量: 238.076
• InChiKey: IXJPGPFLQYXMCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,9-dichloro-[1,2,3]triazolo[1,5-a]quinoline 在 硫酸 、 水 作用下， 反应 24.0h， 以77%的产率得到8-氯-2-喹啉甲醛
  参考文献：
  名称：

  The deprotonative metalation of [1,2,3]triazolo[1,5-a]quinoline. Synthesis of 8-haloquinolin-2-carboxaldehydes

  摘要：

  New highly functionalized triazoloquinolines were synthesized by applying polar organometallic methods. Double metalation and functionalization provided 3,9-dihalogenated triazoloquinolines. Ring opening of the triazole with loss of nitrogen has been performed for the first time with 3,9-dihalogenated triazoloquinolines allowing the access toward 8-haloquinolin-2-carboxaldehydes under oxidant-free conditions. This approach demonstrates that the triazole ring can be used as protecting group of 2-quinolinecarboxaldehydes, activating the C9-position for lithiation and functionalization by triazole ring opening. 8-Haloquinoline-2-carbaldehydes become in this way readily available. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.058
• 作为产物：
  描述：

  [1,2,3]triazolo[1,5-a]quinoline 在 正丁基锂 、 1,1,2-三氯三氟乙烷（CFC-113） 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以71%的产率得到3,9-dichloro-[1,2,3]triazolo[1,5-a]quinoline
  参考文献：
  名称：

  The deprotonative metalation of [1,2,3]triazolo[1,5-a]quinoline. Synthesis of 8-haloquinolin-2-carboxaldehydes

  摘要：

  New highly functionalized triazoloquinolines were synthesized by applying polar organometallic methods. Double metalation and functionalization provided 3,9-dihalogenated triazoloquinolines. Ring opening of the triazole with loss of nitrogen has been performed for the first time with 3,9-dihalogenated triazoloquinolines allowing the access toward 8-haloquinolin-2-carboxaldehydes under oxidant-free conditions. This approach demonstrates that the triazole ring can be used as protecting group of 2-quinolinecarboxaldehydes, activating the C9-position for lithiation and functionalization by triazole ring opening. 8-Haloquinoline-2-carbaldehydes become in this way readily available. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.058

文献信息

• The deprotonative metalation of [1,2,3]triazolo[1,5-a]quinoline. Synthesis of 8-haloquinolin-2-carboxaldehydes
  作者：Rafael Ballesteros-Garrido、Frédéric R. Leroux、Rafael Ballesteros、Belén Abarca、Françoise Colobert

  DOI：10.1016/j.tet.2009.03.058

  日期：2009.5

  New highly functionalized triazoloquinolines were synthesized by applying polar organometallic methods. Double metalation and functionalization provided 3,9-dihalogenated triazoloquinolines. Ring opening of the triazole with loss of nitrogen has been performed for the first time with 3,9-dihalogenated triazoloquinolines allowing the access toward 8-haloquinolin-2-carboxaldehydes under oxidant-free conditions. This approach demonstrates that the triazole ring can be used as protecting group of 2-quinolinecarboxaldehydes, activating the C9-position for lithiation and functionalization by triazole ring opening. 8-Haloquinoline-2-carbaldehydes become in this way readily available. (C) 2009 Elsevier Ltd. All rights reserved.