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有机化学
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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

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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2a～2d 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3a～3d, 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 2a～2d 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 3a～3d by nucleophilic substitution reaction in alkaline solutions. The structures of the title compounds 2a～2d and 3a～3d 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