| Recent years, the research of green chemistry is a hot topic due to the strengthening environmental consciousness. Acidic ionic liquid is an important synthetic route of green chemistry due to their unique physical and chemical properties. The preparation and development of Lewis acidic ionic liquid, Bronsted acidic ionic liquid and supported acidic ionic liquids widened the application of acidic ionic liquid in organic synthesis.Acidic ionic liquid was found to catalyze the oxa-Michael addition reaction for the first time. The experimental results demonstrated that various alcohols proceeded smoothly with methyl vinyl ketone and acrylaldehyde, furthermore, O-selectivity addition of 2-(benzylamino)ethanol was also achieved. The effect of anions and cations, amount of ionic liquid, temperature, ratio, time and the structures of alcohols on the reaction was investigated. Comparing with traditional acidic imidazolium ionic liquids and organic acids, amides-based acidic ionic liquids gave the better results. Based on the results, a mechanism was postulated and the evidence for the role of amides-based acidic ionic liquids in promoting the oxa-Michael addition reaction had been given.Acidic ionic liquid was firstly found to catalyze the selective addition of hydroxybenzenes. The selective addition reaction of various hydroxybenzenes with methyl vinyl ketone, acrylaldehyde and acrylonitrile proceeded smoothly. The effect of anions and cations, amount of ionic liquid, temperature, ratio, time and substituents on the reaction was investigated. The results demonstrated that the position and nature of substituent had important influence on the selectivity of addition. Based on the results, the possible mechanism of selective addition catalyzed by acidic ionic liquids had been given.The synthesis of 1,2,3,4-tetrahydroquinoline derivatives catalyzed by acidic ionic liquid was explored. The influences of anions and cations, amount of ionic liquid, temperature, ratio, time, solvent on the reaction was investigated. Comparing with the result in acidic ionic liquid, the better result could be obtained in acidic ionic liquid/CH3Cl and a series of novel 1,2,3,4-tetrahydroquinoline compounds were synthesized. Based on the results, a possible process of the cascade reaction was postulated and the evidence had been given. In the thesis,64 compounds were synthesized including 13 ionic liquids,18 oxa-Michael adducts,9 C-alkylated products,7 O-alkylated products,8 2-(phenylamino)ethanol derivatives,6 1,2,3,4-tetrahydroquinoline derivatives and 3 N-adducts. These compounds were characterized by 1H NMR,13C NMR, FTIR, HRMS and 30 compounds have been confirmed to be new compounds.
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