Study On The Synthesis Of Monosubstituted-1,2,3-triazole

1,2,3-Triazole is a kind of five-membered aryl compounds,in which the core contains two carbon atoms and three continue nitrogen atoms.These heterocycles have been widely used in many fields including medicine,insecticide,and materials.Though the structure is simple,mono-substituted 1,2,3-triazoles are more difficult to synthesized than di-substituted ones.The main contents of the thesis are as follows:In chapter 1,we reviewed the recent progress of the 1,2,3-triazoles in recent years,mainly including its applications in medicine and organic synthesis,and the development of the preparation of mono-substituted 1,2,3-triazoles.In chapter 2,we explored the synthesis of mono-substituted 1,2,3-triazoles using propiolic alcohol as the“acetylene source”.We chose the reaction of1-azido-4-methylbenzene and propargyl alcohol as the model to explore and obtained the optimized reaction conditions as following.Step 1:1-azido-4-methylbenzenes 1?0.3 mmol?,propargyl alcohol 2?0.36 mmol?,CuI?0.03 mmol?,NaAsc?0.06 mmol?,and 2 mL solvent were added to a 15 mL pressure tube.The tube was then sealed,and the mixture was stirred at 80°C for 5 hours.Step 2:the above system was added with KMnO₄?0.75 mmol?and Na₂CO₃?0.45 mmol?,and stirred at 80°C for 8 hours until the reaction completed.Step 3:Ag₂O?0.03 mmol?and K₂S₂O₇?0.6 mmol?were added to the tube and the mixture was conducted at 100°C for 24 hours until the transformation finished.Under the optimized reaction conditions,we synthesized a series of mono-substituted 1,2,3-triazoles with good yields and good group compatibility.In chapter 3,we explored the synthesis of mono-substituted 1,2,3-triazoles using2-methyl-3-butyn-2-ol as the“acetylene source”.We chose the reaction of1-azido-4-methylbenzene and 2-methyl-3-butyn-2-ol as the model to explore and obtained the optimized reaction conditions as following:aryl azides 1?0.3 mmol?,2-methyl-3-butyn-2-ol 2?0.3 mmol?,CuI?0.015 mmol?,NaAsc?0.03 mmol?and KOH?1.5 mmol?were added to 2 mL of solvent and stirred at 130 ^oC for 48 h.Through the optimized reaction conditions,we synthesized a series of mono-substituted 1,2,3-triazoles with good yields and good group compatibility.In Chapter 4,the summary of main results of this thesis was demonstrated and further work was also proposed.