Synthesis Of New 1,5-benzodiazepine Derivat-ives Containing 2-Phenyl-1,2,3-trizaole And Pyrazoles Derivatives

The 1,5-benzodiazepine is an important kind of seven-membered ring heterocycliccompound, which is widely used in synthetic drugs. 1,5-benzodiazepine and itsderivatives have a wide range of biological activities such as anticonvuisant,antianxiety, antidepression and so on. They are often used as tranquilizer-hypnoticsand antiviral drugs. So, scientists pay great attention to their synthesis, structure, andavtivites research. Compounds containing 1,2,3-triazole exhibit great pharmacologicalactivites, including antibiosis, anti-HIV and so on. Therefore, we synthesized a seriesof novel 1,5-benzodiazepines. Much research work has been shown that compoundswith 1,2,4-oxadizole have the properties of antibiosis and anti-inflammatory. Wecombined 1,2,4-oxadizole with 1,5-benzodiazepines by 1,3-dipolar cycloadditionreaction, and obtained a series of novel tricyclic condenst 1,5-benzothiazepinesderivatives. In addition, compounds with a pyrazole ring have insecticidal andherbicidal activites. They play an important role in medicine and pesticide. Weobtained a series of pyrazoles derivatives by the reaction ofα,β-unsaturated ketoneswith thiosemicarbazide, sydnone.The thesis includes two major parts:The first part is about literature review:In this part, the important synthetic methods, activities of l,5-benzodiazepinederivatives that have been studied in China and other countries were explicatedsystematically; and also introduced a more comprehensive properties and syntheticmethods of 1,2,3-triazole; and briefly elucidated 1,3-dipolar cycoladdition reactionand the synthetic methods of pyrazoles.The second part is about experimental content. Major works as follows:1. Synthesis and characterization of 3-aryl-5-(2-aryl-1,2,3-triazol-4-yl)-1-(4-aryl-2- thiazoyl)-pyrazolines1-aryl-3-(2-aryl-1,2,3-triazol-4-yl)-2-propen-1-ones were obtained by the reaction of 2-aryl-4-formyl-1,2,3-triazoles with 1-arylethanones, then the reaction of the compuonds withthiosemicarbazide afforded the key intermediates 3-aryl-5-(2-aryl-1,2,3-triazol-4-yl)-1-thiocarbamoyl-pyrazolines, the condensation of these compounds with 2-bromo-1-arylethanonesresulted in the formation of 3-aryl-5-(2-aryl-4-1,2,3-triazolyl)-1-(4-aryl-2-thiazoyl)-pyrazolines.2. Synthesis and characterization of 4-benzoyl-3-phenyl-5-(2-phenyl-1,2,3-triazol-4- yl)-isoxazolines and 1-aryl-3-(2-phenyl-1,2,3-triazol-4-yl)-4-arylformyl-pyrazolesThe reaction of chalcones containing 2-phenyl-1,2,3-triazole ring withchlorobenzoldoxime, syndone afforded a series of isoxazolines and pyrazolesderivatives containing 2-phenyl-1,2,3-triazole ring.3. Synthesis and characterization of novel 1,5-benzodiazepines with 2-phenyl-1,2,3-triazole ring and their derivatives1,5-benzodiazepines with 2-phenyl-1,2,3- triazole ring were obtained by thereaction of chalcones containing 2-phenyl-1,2,3-triazole and o-phenylenediamine,then the reaction of the ptoducts and chlorobenzoldoxime afforded the1,5-benzodiazepines derivatives with both 1,2,3-triazole ring and 1,2,4-furodiazolering.Above all, the structures of the new compounds were confirmed by elememtalanalysis, IR, 1H NMR and MS spectral data, and their spectral property were alsodiscussed.