Synthesis Of 1,4-Substituted 1,2,3-Triazoles And Amination Reaction Of Aryl Halides Catalyzed By Cu-MOF

Nitrogen-containing compounds have wide applications in functional materials,chemical production,natural products,and active pharmaceutical ingredients.Therefore,it is an active research field to find alternative methods to construct carbon-nitrogen bonds easily.1,2,3-Triazole is an important nitrogen-containing heterocyclic and structure method in lots of chemical molecules,which are widely used in medicinal chemistry,chemical engineering,biological sciences,and materials science.The amination of aryl halides to prepare arylamines and diarylamines is also a very important method in the construction of C-N bond.Nowadays,the increasing environmental awareness encourages chemiststo seek for more environmentally friendly chemical production processes.For these purposes,the development of new heterogeneous recyclable catalysts and the use of less toxic materials as solvents and reagents are two important challenges.The thesis consists of three chapters:Chapter 1: Methods for the syntheses of 1,2,3-triazole derivatives are summarized.The research progress of the amination reaction of aryl halides is also reviewed in detail.Chapter 2: A simple and efficient method for thesynthesis of 1,4-disubstituted 1,2,3-triazolesderivatives is developed.Under mild reaction conditions,Cu(BTC)-MOF was used as the catalytic material for three-component cycloaddition of terminal acetylene,alkyl halides and sodium azide to obtain 1,4-disubstituted 1,2,3-triazole derivatives.The reaction was conducted inmethanolat room temperature.22 examples were given with the product yield up to 91 %.The catalytic material was recycled to use at least three times without significant loss of catalytic activity.The advantages of this method are mild reaction conditions,simple procedure,wide scope of substrates,cleaner process and good to excellent product yields.Chapter 3: In this chapter,amination reaction of aryl halides or heteroaryl halides catalyzed by Cu(BTC)-MOF is described.The reaction was performed with ammonia water as an aminating agent at 120 °C for 30 minutes and diarylamines was obtained exclusively in most cases with the yield of 54 % ~ 89 %.Obviously,it is a practiceable method for the amination of aryl halides by using cheap copper catalyst and ammonia water as a nitrogen source.