1,2 - The Reduction Reaction Of The Imidazoline Two Fluorescent Probes Dyes Carbon Rhodamine Intermediates Synthesized

This thesis contains two parts:research on the reduction reaction of 2-imidazoline and the synthesis of fluorescence probe dyes carbon-rhodamine analogues intermediates.Part I:Research on the reduction reaction of 2-imidazoline. As an important kind of heterocyclic scaffolds,2-imidazolines drawed the attention from the chemists interested in pharmaceutical chemistry, synthetic organic chemistry, natural products, coordination chemistry, homogeneous catalysis and so on. In the past two decades, in order to fulfill the demand of structural diversity, many synthesis methods have been improved. Though the synthesis methods almost approaches the perfect, there is little research on the reduction of 2-imidazoline. At present, only our research group has preliminary studied on 2-imidazolines's reduction under NaBH4/HCl system.In this thesis, the new reduction reaction of 2-imidazoline was studied in this thesis. Six representative 2-imidazolines were prepared and their reductions were studied under NaBH4/I2 system, NaBH4/CoCl2 system, NaBH4/AlCl3 system, NaBH4/ZnCl2 system, NaBH4/CeCl3 system and NaBH4/TiCl4 system. The chemical structures of the products were identified and confirmed by IR, MS, GC-MS,1H NMR and so on. The effects of different reduction systems and different 2-imidazolines on reduction reactions were studied in this work, and at the same time, the reduction mechanisms of different reaction systems were discussed in this thesis. The results show that 2- imidazolines opened their rings under these six reduction systems, produced unsymmetrical substituted ethylenediamine derivatives. Among these reduction systems, NaBH4/12 system shows the best reduction ability. Not only the reduction reactions under different NaBH4 systems, but also an important method in organic synthesis for unsymmetrical substituted ethylenediamine derivatives was provided in this thesis. This work plays an important role in basic research in organic chemistry and applied research.PartⅡ:The synthesis of fluorescence probe dyes carbon-rhodamine analogues intermediates. The design and synthesis of organic fluorescent dyes and their biological applications are a hot topic in organic chemistry and biology research. Because they can effectively avoid the interference from the biological background fluorescence and have good penetration to cells, long-wavelength fluorescent probe dyes are popular used. Carbon-rhodamine is a class of very good performance potential fluorescent probes dyes, which has high fluorescence quantum yields and big fluorescence spectra red-shift amplitude. At present, a little synthesis methods have been reported.This thesis designs to synthesize a new type of carbon-rhodamine organic fluorescent dyes. This experiment first designed to synthesize N, N-dibenzylamino-3-isopropenyl aniline (intermediateⅠ) and 2-(4'-N, N-Dibenzylamino) benzoic acid (intermediateⅡ), and then these two intermediates occur electrophilic substitution reaction on the aromatic ring to the obtain target compound in acidic conditions. The intermediate (Ⅰ) of dye was prepared by esterified, amido-protected, alcoholized and dehydrated from m-aminobenzoic acid. The chemical structures of the products were identified and confirmed by IR and GS-MS. The synthesis of intermediate (Ⅱ) is in progress. The synthesis of intermediate (Ⅰ) provides a theoretical basis and practical combination of process parameters for the further synthesis.