有机化学 ›› 2010, Vol. 30 ›› Issue (08): 1180-1184. 上一篇    下一篇

研究论文

Friedl?nder反应合成新型喹啉衍生物及其结构表征

吴利欢*,1,杨定乔2   

  1. (1肇庆学院化学化工学院 肇庆 526060)
    (2华南师范大学化学与环境学院 广州 510006)
  • 收稿日期:2009-11-25 修回日期:2010-02-05 发布日期:2010-03-10
  • 通讯作者: 吴利欢 E-mail:zqwlh@126.com

Friedl?nder Synthesis and Structure Characterization of Novel Qui-noline Derivatives

Wu Lihuan*,1 Yang Dingqiao2   

  1. (1 School of Chemistry and Chemical Engineering, Zhaoqing University, Zhaoqing 526060)
    (2 School of Chemistry and Environment, South China Normal University, Guangzhou 510006)
  • Received:2009-11-25 Revised:2010-02-05 Published:2010-03-10

以取代和未取代的邻氨基苯甲醛与6-氟-4-色满酮为原料, 在碱性的醇溶液中发生Friedl?nder 缩合反应, 除了得到预期的 2-氟-6H-色满并[4,3-b]喹啉及其衍生物2a2d 外, 还发现这类化合物在碱性溶液中会进一步发生亲核取代反应, 生成2-(3-乙氧甲基)喹啉基-4-氟苯酚及其衍生物3a3d, 它们的结构通过元素分析, IR, 1H NMR和MS进行了鉴定和表征, 并用X射线衍射法测定了化合物3d的晶体结构.

关键词: Friedl?nder缩合反应, 亲核取代反应, 6-氟-4-色满酮, 晶体结构

A series of 2-fluoro-6H-chromeno[4,3-b]quinoline derivatives 2a2d were synthesized by the Friedländer condensation of substituted (unsubstituted) o-aminobenzaldehyde with 6-fluorochroman-4-one in alkaline ethanol solutions. In addition, the expected products can give 2-(3-(ethoxymethyl)quinolin-2-yl)- 4-fluorophenol derivatives 3a3d by nucleophilic substitution reaction in alkaline solutions. The structures of the title compounds 2a2d and 3a3d were characterized by elemental analysis, IR, 1H NMR and MS techniques. The compound 3d was confirmed by X-ray single crystal diffraction analysis.

Key words: Friedländer condensation, nucleophilic substitution reaction, 6-fluorochroman-4-one, crystal structure