Synthesis And Characterization Of Tetrazole And Triazole Compounds

Tetrazole and triazole rings, as the representative five-membered heterocycliccompounds, are widely used in many field of chemistry because they have the uniquestructures and properties, higher nitrogen content, and aromatic properties. In recentyears, Tetrazole and triazole compounds become one of the hot topics in the study ofchemical industry. In view of their important application value, a series of tetrazoleand triazole compounds have been syntheiszed in this thesis.1. The synthesis of tetrazole compounds. Firstly,3-fluoro-4-(1H-tetrazol-5-yl)-phenol was syntheiszed by the reaction of3-fluoro-4-cyanophenol with sodium azideusing toluene as solvent, and hydrochloric acid/triethylamine as catalyst. Then fivenew tetrazole compounds, namely,2-(3-fluoro-4-(1H-tetrazol-5-yl)phenoxy)aceticacid,2-((3-fluoro-4-(1H-tetrazol-5-yl)phenoxy)methyl)-1H-benzoimidazole,1,2-bis(3-fluoro-4-(1H-tetrazol-5-yl)phenoxy)ethane,1,3-bis(3-fluoro-4-(1H-tetrazol-5-yl)-phenoxy)propane, and1,4-bis-(3-fluoro-4-(1H-tetrazol-5-yl)phenoxy)butane, weresyntheiszed by the reaction of3-fluoro-4-(1H-tetrazol-5-yl)phenol with chloroaceticacid,2-chloromethyl-1H-benzoimidazole, dichloroethane, dibromopropane anddibromobutane, respectively. These tetrazole compounds were characterized bynuclear magnetic resonance (NMR) and infrared spectrum.2. The synthesis of triazole compounds. Firstly,1-azido-4-nitrobenzene wassyntheiszed by the reaction of4-nitrobenzenamine with sodium azide and sodium nitrite in hydrochloric acid.5-Methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylic acid was syntheiszed by the reaction of1-azido-4-nitrobenzene with ethylacetoacetate in the presence of ethanol/sodium ethanolate. Similarly,5-methyl-1-(4-carboxyphenyl)-1H-1,2,3-triazole-4-carboxylic acid was syntheiszed by using4-aminobenzoic acid as starting material. These triazole compounds werecharacterized by nuclear magnetic resonance (NMR) and infrared spectrum.