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DMF catalytic synthesis of 1, 4, 5- three instead of -1 2, 3- three, triazole derivatives

Author: HouYaLan
Tutor: XuFeng
School: Shaanxi Normal University
Course: Organic Chemistry
Keywords: DMF the compounds of triazoles azide benzene 1,2,3-triazides
CLC: O626.2
Type: Master's thesis
Year: 2013
Downloads: 91
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Abstract


Triazoles is a kind of important compounds, it has two kinds of structure, one is1,2,3-triazide compounds and another is1,2,4-triazide compounds. Because of its unique biological activity,1,2,3-triazide compounds have drawn much attention in recent years. Due to its special resistance for strong acid and strong alkali, and lower toxicity than imidazole group,1,2,3-triazide compounds have been widely applied to organic chemistry, medicinal chemistry, material chemistry and biochemistry research field.1,2,3-triazide structure unit are frequently found in many kinds of drugs. Therefore, much attention has been paid to triazoles compounds in recent years. Synthesis1,2,3-triazide becames one of the most active research fields to synthesis chemist.At present, there are many report relevant the synthesis1,2,3-triazide compounds. The Huisgent1,3-dipolar cycloaddition reaction of azide and alkyne,which catalyzed by Cu, has attracted widespread attention for its fast reaction rate and good selectivity. But only the terminal alkyn can get good yields. Moreover, the residual copper salts aslo have cytotoxicity to organism. Although, lots of small organic molecules were developed for catalyzed synthesis of1,2,3-triazide. But there are more or less limitations for above process.Based on the above research background and predecessors’ research works, we tried to develop a new process for synthesis1,2,3-triazide compounds in order to achieve convenient operation, atom economy, shorter reaction time, high yield, which use DMF as a catalyst, azide benzene derivatives and acetyl acetone or other ketone as starting material.This thesis mainly includes three parts:First part:the new development of synthetic methods and application of the1,2,3-triazide compounds were reviewed, especially in the field of medicine. Then, the nature of DMF and its application in the organic synthesis were also introduced in the end of the part.Second part:the synthesis of azide benzene derivatives was reported. Azide benzene derivatives is one of the raw materials for synthetic1,2,3-triazide compounds, which were synthesized by aniline and its derivatives. A series of azide benzene derivatives were synthesized and characterized by IR,1H NMR and13C NMR. All the analysis data are consistent with the expected structure.Third part:The new process for synthesis of1,2,3-triazide compounds were demonstration. First, different catalyst were used to catalyz the azide benzene and acetylacetone reaction for synthesis1,2,3-triazide compounds. The result shown DMF is the best one. Then, under the DMF catalyst, azide benzene and acetylacetone were used as starting material for screening the optimum reaction condition. After the optimum reaction condition was obtained, azide benzene derivative and other acetone were used to prepare the different1,2,3-triazide compounds. All the compounds were charaterized by IR,1H NMR and13C NMR. All the analysis data are agree with the expected structure. The results prove this new process have widely applicable scope, convenient operation and fast reaction rate.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Heterocyclic compounds > Containing five pairs or more different atoms of heterocyclic
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