Synthesis And Bioactivity Study Of Tertazole, Thiadiazole Heterocyclic Derivatives

This thesis includes three sections.Section one.Chapter 1. This chapter is a brief review for the research, synthetic methods and application values of tetrazole derivatives in recent years.Chapter 2. The synthesis of arylaldehyde-N-(1-phenyl-1H-tetrazole-5-yl)thiol acetyl hydrazones under the condition of microwave irradiation conditions were elucidated. By using this method, the reaction time was shortened rapidly and the yields of the products were enhanced but the solvent was reduced. The experiment results indicated it is an efficient and convenient method for the synthesis of Arylaldehyde-N-(1-phenyl-1H-tetrazole-5-yl) thiol acetyl hydrazone compounds. Moreover, the single crystal structure of benzylaldehyde-N-(1-phenyl-1H-tetrazole -5-yl) thiol acetyl hydrazone was analyzed by X-ray diffraction. It was found that intermolecular hydrogen bond exists between N-H and O atom. The crystal structure shows that the compound has trans configuration and characteristic dimers connected by intermolecular hydrogen bond. The bioactivity screen indicated that some compounds have properties of anti-coliform.Section twoChapter 3. This chapter is a brief review for the research, synthetic methods and application values of thiadiazole derivatives in recent years.Chapter 4. Six kinds of alkyl-substitute compounds compounds and nine kinds of acylhydrazone compounds based on 2,5-bismercapto-1,3,4-thiadiazole derivatives were synthesized. The best conditions in synthesis this kind of compound were also studied. Furthermore, a series of Aroyl isothiocyanates were synthesized under the condition of solid-liquid phase transfer catalysis. Then, a series of bis-thiosemicarbazides based on thiadiazole ring could be obtained by the addition reaction between aroyl isothiocycanates with acylhydrazide. Some heterocyclic derivatives containing three thiadiazole rings could be prepared by the method of dehydration of these acylthisemicarbazides in concentrated H₂SO₄ at 0°C. The bioassay result indicated that some compounds have bioactivity of anti-bacterium or improving plant growth. All these compounds were confirmed by EA, IR, ¹H NMR and ¹³C NMR.Chapter 5. In this section, the supramolecular anion recognition using thiourea derivatives as host is reviewed. In the following parts, via the reaction between glyoxal and a series of arylthiosemicarbazides, aryloxyacetic hydrazide, nine kinds of hydrazone compounds were synthesized conveniently. The anion recognition properties of them were examined by UV-Vis and ¹H NMR spectroscopy in DMSO. The UV-Vis data indicated that a 1:1 stoichiometry complex was formed between receptors and the three anions. ¹H NMR titrations and solvation effect confirmed hydrogen interaction between the receptors and anions.