9-fluoro-5-phenyl-[1,2,3]triazolo[5,1-a]isoquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 9-fluoro-5-phenyl-[1,2,3]triazolo[5,1-a]isoquinoline
• 英文别名: 9-Fluoro-5-phenyltriazolo[5,1-a]isoquinoline；9-fluoro-5-phenyltriazolo[5,1-a]isoquinoline
• 化学式: C₁₆H₁₀FN₃
• 分子量: 263.274
• InChiKey: ABIBDHMVLBAYJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  30.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-氟-2-(2-苯乙炔基)苯甲醛 在 sodium azide 、 ammonium acetate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.5h， 生成 9-fluoro-5-phenyl-[1,2,3]triazolo[5,1-a]isoquinoline
  参考文献：
  名称：

  Synthesis of Triazolo Isoquinolines and Isochromenes from 2-Alkynylbenzaldehyde via Domino Reactions under Transition-Metal-Free Conditions

  摘要：

  We describe two simple straightforward syntheses of triazolo isoquinolines (3) and isochromenes (7) from 2-alkynylbenzaldehydes (1) as a common synthon. The synthetic strategy for 3 involves formation of the (E)-1-(2-nitrovinyl)-2-(alkynyl)benzene species 2 via condensation of synthon 1 with nitromethane followed by a [3 + 2] cycloaddition/extrusion of the nitro group/regioselective 6-endo cyclization domino sequence. In yet another strategy, the synthon 1 was condensed with nitromethane followed by electrophilic iodo cyclization of the resulting 2-nitro-1-(2-(alkynyl)phenyl)ethanol (6) to furnish iodo isochromene derivatives. The salient feature of the above two strategies involves formation of the corresponding heterocycles under metal-free conditions in good yields.

  DOI：

  10.1021/jo401929q

文献信息

• Facile Synthesis of [1,2,3]Triazolo[5,1-<i>a</i>]isoquinolines through a Copper-Catalyzed Tandem Sonogashira Coupling/Cyclization Reaction
  作者：Mingzhu Fan、Yi Liu、Qinquan Hu、Lihui Jia、Yunfeng Chen

  DOI：10.1002/ejoc.201601188

  日期：2016.11

  A highly efficient synthesis of [1,2,3]triazolo[5,1-a]isoquinoline derivatives was developed that proceeds through copper-catalyzed tandem Sonogashira coupling/regioselective 6-endo cyclization. This NH-triazole-directed annulation approach showed good functional-group tolerance and gave the corresponding N-fused heterocycles in good to excellent yields.

  开发了 [1,2,3] 三唑并 [5,1-a] 异喹啉衍生物的高效合成，其通过铜催化串联 Sonogashira 偶联/区域选择性 6-内环化进行。这种 NH-三唑导向的环化方法显示出良好的官能团耐受性，并以良好到极好的产率得到相应的 N-稠合杂环。