Studies On The Synthesis Of Substituted 1,2,3-triazoles

As one unique nitrogen-containing heterocyclic scaffold,the 1,2,3-triazole derivatives are widely used in the fields of biological science,material chemistry,pharmaceutical chemistry and organic synthesis chemistry because of their unique structure and chemical properties.Due to the importance of these compounds in many fields,they have been received extensive attention in recent years.Up to now,there are no reports on the isolation of 1,2,3-triazoles from natural products.Therefore,it is very important to develop a new,green and efficient synthetic method of 1,2,3 triazole compound.According to the different catalytic systems,the synthesis of disubstituted-1,2,3 triazole compounds can be divided into copper metal catalyzed,silver,palladium,ruthenium and non-metal catalyzed synthesis methods.In recent years,many classical organic synthesis reactions have been realized in green solvents represented by water,ionic liquids and biomass solvents.According to the detailed literature,the green solvent and the synthesis of substituted-1,2,3-triazole compounds were skillfully combined.In general,the research contents of this paper are mainly divided into two parts:First,a series of 1,4-disubstituted 1,2,3-triazoles were synthesised using a cheap and easily available combination of CuI/Et₂NH as catalyst system,using green solvent glycerol as reaction solvent from organic halides,terminal alkynes and sodium azide at room temperature.This synthesis method of"one-pot three-component"is simple and easy to operate,with wide application range,mild reaction condition,up to99%of the yield,and the amplification reaction is easy to be realized,it has high application value.Second,a series of 1,4,5-trisubstituted 1,2,3-triazoles were synthesised using a cheap and easily available combination of CuI/Et₂NH as catalyst system,using green solvent glycerol as reaction solvent from organic halides,non-terminal alkynes and sodium azide at 100?.This method has the advantages of simple operation,wide application range of substrate and mild reaction conditions.The main highlights of this paper are as follows:1.A new catalytic system was designed to catalyze and synthesize substituted 1,2,3-triazoles.The catalytic system composed of cuprous iodide and diethylamine was cheap and easy to be prepared,which made the synthesis of substituted 1,2,3-triazoles more convenient.2.The substituted 1,2,3-triazoles were successfully synthesized in green solvent glycerol,which provided a new choice for the suitable solvent of 1,2,3-triazoles.3.22 kinds of 1,4-disubstituted 1,2,3-triazoles and 12 kinds of 1,4,5-trisubstituted 1,2,3-triazoles were synthesized.The structure of synthetic compounds was determined by ¹H NMR,¹³C NMR,and high resolution mass spectrometry.4.The reaction mechanism of the synthesis of substituted 1,2,3-triazoles was studied.The reaction mechanism of 1,4 disubstituted 1,2,3-triazole compound was verified by experiments.The solvent effect of the synthesis of 1,4-disubstituted 1,2,3-triazole compound was studied.