Synthesis Of Novel Thiobenzenesulfonate Derivatives And Polycyclic Quinolinesulfonamides

Nitrogenous heterocyclic compounds become a focal point of research due to the characteristics of structural changes and their high biological activities. The nitrogenous heterocyclic compounds can be modified easily structurally with various functional groups. Glucosinolates benzene sulfonic acid esters derivatives have many good biological activities, which synthesized based on the formation of C-S bond, are widely used in medicine and pesticide industry. Quinoline derivatives are a kind of important nitrogen heterocyclic compounds. In recent years, numerous reports have been developed for quinoline compounds because of their wide range of biological activities: anti-inflammatory, malaria, antibacterial, anti alzheimer’s disease, antihypertensive and anti-HIV activity, and they also can be used as the intermediate of synthesis of other nitrogen heterocyclic compounds, quinoline compounds has attracted a lot of attention. Recently, about polycyclic quinoline derivatives such as camptothecin, indene and quinoline derivatives can effectively inhibit topoisomerase I, it has been widely applicated and attracted a lot of attention in the medical industry and clinical treatment. This paper has carried out the following main work because of the above two compounds of pharmacological activities.In chapter one, the recent research progress of heterocyclic ketene amine has been reviewed.In chapter two, an efficient and convenient method was developed for the preparation of2-benzenesulfonothiol-HKAs via a silver(Ⅰ)-mediated direct sulfenylation of heterocyclic ketene aminals (HKAs). With heterocyclic ketene amine1-3and benzene sulfonyl double4as raw materials, using silver acetate as catalyst and reflux in dioxane, a seires of highly selective sulfone compounds5-7with potential biological activites has been synthesized. The method involves a variety of functionalized substrates, leading to a-arylthioyl HKAs in a mild, easy operation, and mild reaction conditions. In chapter three, an efficient method was developed for the synthesis of novel polycyclic quinoline sulfonamide with heterocyclic ketene aminals as building block. Firstly, indole sulfonyl chloride3was synthesized from indole quinone2. Then3react with HKAs under the catalysis trimethylamine to give29novel polycyclic quinoline sulfonamide compounds10-12and17-18. The reaction has the advantages of readily available starting materials, simple synthetic route, high yields and simple work-up procedures.The structure of the above two categories, a total of47compounds were characterized by IR,1H NHR,13C NMR and MS spectra.one of the compounds are characterized by x-ray.