The Synthesis Research Of N-(1-Alkenyl) Azoles

N-(1-Alkenyl)azoles have showed excellent biological activities,such as inantibacterial,anticancer and antiviral etc.N-(1-Alkenyl)azoles also are important building blocks in the synthesis of many biologically active molecules.Thus,the synthesis of N-(1-Alkenyl)azoles had been focused.Firstly,the biological activities and synthetic methods of N-(1-unsaturated hydrocarbon)azoles were reviewed.On this basis,this thesis described a new method to synthesis N-(1-Alkenyl)azoles with 1,1-dihaloalkenes and 1H-azoles as starting materials in the present of base.The optimized reaction condition was determined : at the present of NaOH without catalyst.A series of N-(1-Alkenyl)azoles were obtained with good yields which 29 1,1'-(1,1-diyl)bis(1H-azoles)and 12 1,1'-(1,2-diyl)bis(1H-azoles),all the synthesised compounds were not reported yet.The structures of new compounds were characterized by NMR,Single crystal X-ray diffraction,IR and MS.Secondly,the application scope of the reaction conditions was explored.1,1-dibromo-2-aromatic hydrocarbons substituted vinyl and 1,1-dibromo-2-aliphatic hydrocarbons substituted vinyl were conducted in the optimized reaction condition,both the two compounds showed a good reaction activity with yields between 46% to 95%;The reaction activity of(2,2-dichlorovinyl)benzene was also explored,and the yields were above 60%.This method also performed well with 1H-azoles,the yields of 1H-pyrazoles,1H-imidazoles and 1H-triazoles reacted to 2,4-dichloro-1-(2,2-dibromovinyl)benzene were above 60%.At last,the mechanism of this reaction was proposed and studied.The intermediates of bromoethyne were synthesized,then bromoethynes reacted with 1H-azoles leading to 1-ethynyl-1H-azoles in the present of NaOH.Finally 1H-azoles added to 1-ethynyl-1H-azoles form N-(1-Alkenyl)azoles in the present of NaOH.