The Applications Of Green Synthesis Of Gem-Diaryl Methane Via 1,6-Conjugated Addition

gem-Diaryl methane skeleton,widely existing in natural products and pharmaceutical molecules,is exhibited of significance application value due to its great antibacterial,inhibitive,and cytotoxic activity.However,current synthesis methods on the literature stick in the issues such as expensive/toxic catalysts,additives and organic solvents.(The scope of nucleophilic reagents are almost confined to silyl enol ether,1,3-dicarbonyl compounds,phosphite ester,and so on;nevertheless,rarely are sodium aryl sulfite,electron-deficient arene and N-substituted piperazidine involved.)Therefore,efficient,green,and expedience synthesis of gem-diaryl methane via 1,6-conjugated addition starting from nucleophilic reagents(sodium aryl sulfite,electrondeficient arene and N-substituted piperazidine)and para-Quinone methides display crucial topic.The work of this thesis could be generalized as following:1)We had designed and realized the organic and aqueous phase thio-1,6-conjugated addition of sodium aryl sulfite and para-Quinone methides to construct a kind of gem-diarylmethyl sulfone compound.The reaction had moderate to high yield with 46%-99% yield in organic phase and 42%-99% yield in aqueous phase,broad substrate scope,metal-free catalysis,and convenience in operation without further requirement in the amount of air and water.In addition,the product was verified by single crystal X-ray diffraction analysis to ascertain the chemical composition and spatial structure.Finally,the product was successfully transformed into 1,3-dicarbonyl compound with prochiral carbon atom and unsymmetrical triarylmethane.2)We had designed and realized 1,6-conjugated addition of N,N-dimethylaniline and para-Quinone methides in solvent-free condition to construct a kind of triarylmethane.The reaction had moderate to high yield ranged from 51% to 94% within 16 substrates in the variety of para-Quinone methides.The reaction had metalfree catalysis,and convenience in operation without further requirement in the amount of air and water.In addition,the scope of electron-deficient arene was expanded into 4-hydroxy-2H-chromen-2-one with further single crystal X-ray diffraction analysis of the product.Finally,the product was transform into bioactive 4-(diarylmethenyl)-cyclohex-2,5-dien-1-one via one-step oxidation.3)We had designed and realized a synthesis strategy toward gem-diarylmethyl piperazidine compound and triaryl methane.Compared to current reported,this work has less synthesis procedures,more reaction conditions avoiding expensive/toxic catalysts,additives and organic solvents,and more convenient work-up step.