The Preparation And Characterization Of Poly-substituted Triazole Compounds Basing On The Click Reaction Of Terminal Alkynes And Azides

Multi-component and one-pot reaction is one of the hottest research of organic synthetic methodology at present.1,2,3-Triazole compounds have been widely used in organic synthesis,medicinal chemistry and materials chemistry and other fields. The organic chemists are paying more and more attention to design 1,2,3-Triazole compounds containing novel structure and functional groups, and seek a mild synthetic conditions. In this paper,we used 2,3-dibromo-propylene,terminal alkynes,sodium azide,and sodium iodide as raw materials to take one-pot reaction of three or four components. By this way,we synthesized the 1-allene-4-subsitituted-1,2,3-triazol and such new heterocyclic compounds. We provided theory and experimental basis and its application method for the synthesis of 1,2,3-triazole.The main work of this paper is as follows:Firstly,we used 2,3-dibromo-propylene as raw material,in the presence of Cu(I) catalytic system, reaction with sodium azide and terminal alkyne by Huisgen 1,3-dipolar cycloaddition reaction, a series of corresponding 1-(2-bromo-2-propenyl)-4-substituted-1,2,3-triazole compounds have been made. Followed by the DBU and potassium t-butoxide promote eliminating reaction and rearrangement reaction of double bond to give the novel 1-allene-4-substituted-1,2,3-triazole compounds. This method is simple operation with mild reaction conditions and give high yield.Secondly,we used 2,3-dibromo-propylene as raw material,in the presence of Cu(I) catalytic system,reaction with sodium azide,terminal alkyne and sodium iodide by on-pot of four components Huisgen 1,3-dipolar cycloaddition reaction. We got a series of 1-(2-bromo-2-propenyl)-4-substituted-5-iodo-1,2,3-triazole compounds. This method is simple operation and provided theory and experimental basis and its application method for the synthesis of 1,2,3-triazole.