2-(4-fluorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one | 1208524-11-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-fluorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one
• CAS: 1208524-11-1
• 化学式: C₁₇H₁₂FN₃O
• 分子量: 293.3
• InChiKey: QPONDUVHYGFDBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  39.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-甲基喹啉 、 1-(4-fluorophenyl)hydrazine-1-carbonyl chloride hydrochloride 反应 2.0h， 以72%的产率得到2-(4-fluorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one
  参考文献：
  名称：

  Synthesis of 2-aryl-2H-[1,2,4]triazoloquinolin-3-one and 2-aryl-2H-[1,2,4]triazoloisoquinolin-3-one derivatives from α-chloroformylarylhydrazines hydrochloride

  摘要：

  The reaction of alpha-chloroformylarylhydrazines hydrochloride with quinoline under air provided the corresponding 2 -ary1-2H-[1,2,4] triazoloquinolin-3-ones 3a-3d in 33-42% yields and unexpected isomeric 2-aryl-2H-[1,2,4]triazoloisoquinolin-3-ones 4a-4d in 30-42% yields. These two isomers were isolated and fully characterized by spectroscopic methods including X-ray crystallography. By employing 3-methylquinoline as the starting material under the same condition, the reaction only gave compound 3e-3h as sole products in 70-82% yields without the formation of isomers. A plausible mechanism was proposed through electrophilic aromatic reaction, the tandem ring cyclization and ring-opening, and oxidation for the generation of 2-aryl-2H-[ 1,2,4]triazoloisoquinolin-3-ones (4). Crown Copyright (C) 2009 Published by Elsevier Ltd, All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.095