【摘要】：咪唑并雜環(huán)和吡咯是重要的藥物優(yōu)勢(shì)骨架,廣泛存在于天然產(chǎn)物及藥物分子之中,大部分具有獨(dú)特的生物活性,在生物醫(yī)藥、功能材料等領(lǐng)域有著廣泛的應(yīng)用。因此,探索和研究咪唑并雜環(huán)和吡咯的合成以及基于其骨架的修飾一直是有機(jī)化學(xué)研究的熱點(diǎn)。面對(duì)日益突出的環(huán)境問題,發(fā)展咪唑并雜環(huán)和吡咯的綠色合成方法顯得尤為重要。本論文基于綠色化學(xué)發(fā)展的理念,重點(diǎn)研究了咪唑并雜環(huán)碳?xì)涔倌軋F(tuán)化與構(gòu)建吡咯環(huán)的新方法。本論文分為五部分:(1)歸納總結(jié)了近年來吡咯并喹啉的合成方法;對(duì)咪唑并雜環(huán)碳?xì)涔倌芑姆磻?yīng)類型進(jìn)行了歸納,分別對(duì)咪唑并雜環(huán)的芳基化、烯基化、羰基化、硫化等反應(yīng)進(jìn)行了評(píng)述。(2)探究了六氟磷酸銨促進(jìn)的α-氨基酮的碳?xì)洵h(huán)化,有效合成吡咯并喹啉和吲哚衍生物的反應(yīng)。該反應(yīng)無金屬參與、唯一的副產(chǎn)物是水、后處理簡單、溶劑易于回收循環(huán)使用,有利于環(huán)境保護(hù)。(3)探究了咪唑并雜環(huán)與硫醚的選擇性碳?xì)滏I硫化反應(yīng)。該反應(yīng)以碘為催化劑,過氧化氫為氧化劑,乙醇為溶劑,室溫下反應(yīng)。通過這一綠色的策略能夠在溫和條件下合成多樣性的硫代咪唑并雜環(huán)。(4)探究了咪唑并雜環(huán)與Langlois試劑的選擇性碳?xì)滏I三氟甲基化反應(yīng)。該反應(yīng)是在綠色溶劑離子液體和水的混合溶液中進(jìn)行的。反應(yīng)官能團(tuán)兼容性好,利用這一綠色的策略可以合成多種三氟甲基化的咪唑雜環(huán),也可以合成多種三氟甲基化的苯基取代的咪唑。(5)探究了咪唑并雜環(huán)與2-氨基苯并噻唑的選擇性碳?xì)滏I雜芳基化反應(yīng)。該反應(yīng)無需過渡金屬參與,在亞硝酸叔丁基酯作用下,首次實(shí)現(xiàn)了咪唑并雜環(huán)與2-氨基苯并噻唑的氧化脫氨交叉偶聯(lián)反應(yīng),通過這種簡單、實(shí)用的方法合成了多種高度共軛的雜環(huán)化合物,副產(chǎn)物是水和氮?dú)狻?br/>[Abstract]:Imidazolium heterocyclic and pyrrole are important drug dominant skeletons, which widely exist in natural products and drug molecules. Most of them have unique biological activities and are widely used in biomedicine, functional materials and other fields. Therefore, exploring and studying the synthesis of imidazolium heterocyclic and pyrrole and modification based on its skeleton has been a hot spot in organic chemistry. In the face of increasingly prominent environmental problems, it is particularly important to develop green synthesis methods of imidazole heterocyclic and pyrrole. Based on the concept of green chemistry, this paper focuses on the study of imidazolium heterocyclic hydrocarbon functionalization and the construction of pyrrole ring. This paper is divided into five parts: (1) summarized the synthesis methods of pyrrolidone quinoline in recent years; The reaction types of imidazolium heterocyclic hydrocarbon functionalization were summarized, and the arylation, alkylation, carbonylation of imidazolium heterocyclic were summarized, respectively. (2) the hydrocarbon cyclization of 偽 -aminophenone promoted by ammonium hexafluorophosphate was investigated, and the reaction of pyrroroquinoline and indole derivatives was effectively synthesized. There is no metal participation in the reaction, the only by-product is water, the reprocessing is simple, the solvent is easy to recycle, which is beneficial to environmental protection. (3) the selective hydrocarbon bond vulcanization reaction between imidazolium heterocyclic and sulfides was studied. The reaction was carried out with iodine as catalyst, hydrogen peroxide as oxidant and ethanol as solvent at room temperature. Through this green strategy, various thioimidazole heterocycles can be synthesized under mild conditions. (4) the selective hydrocarbon bond trifluoromethylation of imidazolidazole heterocycles with Langlois reagent was investigated. The reaction was carried out in a mixture of green solvent ionic liquids and water. This green strategy can be used to synthesize various trifluoromethylated imidazole heterocycles. A variety of trifluoromethylphenyl substituted imidazoles can also be synthesized. (5) the selective hydrocarbon bond arylation of imidazolyl heterocycles with 2-aminobenzothiazole was investigated. In the presence of tert-Ding Ji nitrite, the oxidative deamination of 2-aminobenzothiazole with imidazolium heterocyclic was first realized without transition metal participation. A variety of highly conjugated heterocyclic compounds have been synthesized by the practical method. The by-products are water and nitrogen.
【學(xué)位授予單位】：溫州大學(xué)
【學(xué)位級(jí)別】：碩士
【學(xué)位授予年份】：2016
【分類號(hào)】：O626

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