Synthesis Of Novel Monocyclic β-Lactams And 1,2,4--oxadiazolines Drivatives Containing 2-phenyl-1,2,3-trizaoyl

The structure of β-lactams is the active part of many antibiotics. Monocycllic β-lactams antibiotics are known to possess good and antibacterial properties, and the structure is simple so that it can be synthesized easily. As a result, they have been immensely applied in chemotherapy. It is the important position of such compounds in the pharmacological research field that attracts more and more people's interest. Furthermore, many compounds containing 1,2,3-trizolyl have become a hot topic in research of azole compounds because of their vasodilator, anticancer as well as antivirus activites. It has been shown in recent that the pharmacological activities of parent molecules will apparently be improved with the introduction of 1,2,3-triazolyl to some active molecules, such as Penicillin, Cephalosporins and so on. These kinds of compounds have wide applicative prospect. Therefore, we expect to realize reinforcement of physiological activities by means of combining the novel group 2-phenyl-1,2,3-trizolyl with β-lactarn ring and 1,2,4-oxadiazoline ring.In this paper, through modified and controled the experimental conditions of [2+2] cycloaddition reaction, we introduced successfully the group 2-phenyl-1,2,3-triazolyl into monocyclic β-lactam ring. We also introduced the group 1,2,3-triazolyl into 1,2,4-oxadiazoline ring by means of 1,3-dipolar cycloaddition reaction, and a series of derivatives with novel structures were synthesized. It extended the research field of such compounds and provided abundant leading compounds for later selecting work of active compounds.This thesis includes two major parts:The first part is about literature review. The progress in application and synthesis of β -lactams and the progress on 1,3-dipolar cycloaddition reaction in organic synthesis were explicated systematically. In this part, 54 item references were cited.The second part is about experimental content. Major work as follows:1. Synthesis of novel monocyclic β -lactams and 4-thiazolidinones containing 2-phenyl-l, 2,3-triazolyl.We synthesized 2-phenyl-4-formyl-l, 2,3-triazole from glucose via glucosazone-forming, ring closing and oxidation. Condensation of it with arylamine gave imine compounds (Schiff base). Then the Schiff base reacted with chloroacetyl chloride and phenoxyacetyl chloride in presence of triethylamine to yield monocyclic β-lactams derivatives by [2+2] cycloaddition. 4-Thiazolidinones were formed by cyclocondensation of Schiff base and thioglycollic acid. And the spectral properties of products were studied.2.ynthesis of some 3-phthalimido monocyclic β-lactams containing 2-phenyl-l,2,3-triazolylPhthalic anhydride reacted respectively with glycine, L-alanine and DL-alanine, then continue to react with PCls, which produce phthaloylglycyl chloride and phthaloylalanyl chloride. The Schiff base containing 2-phenyl-l,2,3-triazolyl reacted with it in presence of triethylamine to yield monocycllic β-lactams with high stereoselectivity [2+2] cycloaddition. The configration of all new monocyclic β-lactams are all -trans. And the spectral properties of products were studied.3.Synthsis of novel 1,2,4-oxadiazolines containing 2-phenyl-l, 2,3-triazolyl by 1,3-dipolar cycloaddition reaction.The reaction of benzhydroximinoyl chloride, 4-methoxybenzhydroximoyl chloride or 4-nitrohydroximoyl chloride with triethylamine in dry ether gave 1,3-dipolar aryl nitrile oxides. And Schiff base reacted with aryl nitrile oxides, which generated in situ and 21 new 1,2,4-oxadiazolines derivatives containing 2-phenyl-l, 2,3-triazolyl were obtained in good yield by modifying experimental conditions. And spetctral properties were studied.The structrures of all these new compounds that were synthesized were confirmed by elemental analysis, IR, 1H NMR and MS spectral data. The mass spectrums were explained in detail. The cis- or trans- configrations of jtf-lactams were confirmed by certain vicinal proton-proton coupling constants. Some trans-configrations were confirmed by NOESY spectra.The synthesi...