Friedlnder反应合成新型喹啉衍生物及其结构表征

Friedlnder Synthesis and Structure Characterization of Novel Quinoline Derivatives

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,1HNMR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.

A series of 2-fluoro-6H-chromeno4,3-bquinoline derivatives 2a～2d were synthesized by the Friedlander 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.