【作者】 张蕾；

【导师】 梁福顺；

【作者基本信息】 东北师范大学 ， 有机化学， 2009， 硕士

【摘要】 对三联苯及苯基联吡啶类衍生物是一类非常重要的有机中间体。对三联苯类衍生物广泛存在于蘑菇等真菌类植物中。研究发现,三联苯类衍生物具有高生物活性和低毒性等特点,目前已应用于生物、材料、农药、医药等诸多领域。日趋受到人们的关注。同时,α-羰基二硫缩烯酮在有机化学中占有一席之地。结构赋予了这类化合物化学反应的多样性,广泛应用于芳环和杂环的合成中。α-烯酰基二硫缩烯酮属于1,5-双亲电的双Michael受体,可与亲核体发生亲核加成及亲核加成消除等反应。因此,将α-羰基二硫缩烯酮类化合物与三联苯及苯基联吡啶类化合物的合成相关联是一个值得探讨得研究内容。本文以α-羰基二硫缩烯酮为基础,制备了一系列α-烯酰基二硫缩烯酮。分别选用硝基乙烷及醋酸铵为亲核试剂,利用[5+1]成环策略构筑了一系列多取代三联苯及苯基联吡啶衍生物。该种方法产率高效、条件温和、无需金属催化,并得到一组高度多官能化的三联苯及联吡啶衍生物。为三联苯类衍生物的合成提供一种简明有效的方法。更多还原

【Abstract】 p-Terphenyls and heteroaryl analogues including bipyridines are a kind of versatile intermediates in organic synthesis. Chemical investigation of p-terphenyls is one class of the pigments of mushrooms. In recent years, it has been reported that some terphenyls exhibit significant biological activities and low toxicity. Due to their presence as a structural motif in natural products, and their utility in biological, material sciences, agriculture and medicine, p-terphenyls have generated increasing research interest.On the other hand, the utility ofα-oxo ketene-(S,S)-acetals as versatile intermediates in organic synthesis has been recognized. Many compounds with special structures can be constructed from these intermediates. Due to their special synthesis and the construction of natural products,α-oxo ketene-(S,S)-acetals contain two enone fragments. So they should have the potential to be attacked two times by binucleophilic species. Therefore, the combination ofα-oxo ketene dithioacetals and the synthesis of p-terphenyls and heteroaryl analogues deserve investigation.In this thesis, p-terphenyls and heteroaryl analogues including bipyridines were prepared via [5C+1C(N)] annulation ofα-aryl-α-alkenoyl ketene-(S,S)-acetal (five carbon 1,5-bielectrophilic species) with nitroalkanes or ammonium acetate. The reaction features high versatility, mild conditions, multi-substitution, functional group tolerance and metal-catalyst-free. The present protocol provides a new alternative to the conventional methodologies for the preparation of teraryls.更多还原