Synthesis And Properties Of New Quinoline Derivatives

In this paper, the progress of quinoline derivatives in application is summarized. According to a lot of materials, we designed the synthetic route for four novel bisquinolines-6,7-dihydro- dibenzo[b,j][1,10]quinoline derivatives and they have been synthesized successfully by Friedlander condensation reaction.At the room temperature, 2-nitro-4,5-dimethoxy-benzaldehyde (2a), 2-nitro-3,6-dimethoxy-benzaldehyde (2b) and 6-nitropiperonal (2c) have been prepared from veratraldehyde (la), 2,5-dimethoxy-benzaldehyde(1b) and piperonal (1c) in the presence of acetic anhydride with nitric acid. The reduction of (2a-2c) and o-nitrobenzadehyde (2d) with iron powder afforded the corresponding amino aldehyde (3a-3d). With sodium ethoxide as catalyst, the compounds (3a-3d) condensed with 1,2-cyclohexanedione (4) respectively to generate four novel quinoline derivatives (5a-5d). The target compounds (5a-5d) were identified and characterized by MS,UV, IR, 1H NMR and 13C NMR. The optical behavior of (5a) and (5c) were investigated by Fluorescence spectra. The single crystal data of (5a) and (5d) were obtained by X-ray technique and their structures were determined further.In this paper, the binding activities toward calf thymus (CT) DNA of (5a-5d) were investigated by means of spectrophotometric and spectrofluorimetric titrations. The results indicated that all the four target compounds exhibited DNA-binding affinities in the definited concentration.The reaction conditions of Friedlander condensation reaction such as solvent, catalyst, reaction temperature, time and so on were discussed, and every kind of spectrums of target compounds were explained in detail.