本文選題：無過渡金屬　切入點(diǎn)：環(huán)己酮　出處：《湘潭大學(xué)》2017年碩士論文　論文類型：學(xué)位論文

【摘要】：咔唑類化合物是一類重要的有機(jī)含氮雜環(huán)化合物,普遍存在于自然界中,在醫(yī)藥、染料和有機(jī)光電材料等領(lǐng)域中有著廣泛地應(yīng)用,在人類日常生活中具有重要的意義。發(fā)展高效綠色的咔唑合成方法成是有機(jī)合成的研究熱點(diǎn)之一。廉價(jià)易得非芳香性的環(huán)己酮類化合物經(jīng)“脫氫”芳構(gòu)化可以作為潛在的芳基來源,并且已經(jīng)被成功應(yīng)用于有機(jī)合成中。在光電功能材料和藥物合成中重金屬污染與殘留是必須考慮的問題之一,在無過渡金屬參與條件下采用廉價(jià)易得的環(huán)己酮作為芳基來源構(gòu)建咔唑骨架可以提供一條環(huán)境友好的新途徑。本論文以環(huán)己酮為原料在無過渡金屬催化下合成一系列非對稱的N-芳基咔唑類化合物。主要研究內(nèi)容如下:1、發(fā)展了一類以苯基脲類化合物與環(huán)己酮類化合物為原料在無過渡金屬催化下合成非對稱的N-芳基咔唑的方法。該方法無需使用過渡金屬催化劑,官能團(tuán)兼容性較好,咔唑骨架除氮原子外所有原子來源于非芳香性的環(huán)己酮。碘化鉀與單質(zhì)碘共同作為促進(jìn)劑有效促進(jìn)該反應(yīng)的轉(zhuǎn)化,具有中等至優(yōu)良的產(chǎn)率。該反應(yīng)為合成非對稱的N-芳基咔唑提供了一條高效綠色的合成途徑。2、發(fā)展了一類以苯胺類化合物與環(huán)己酮化合物或者與苯乙酮化合物合成咔唑類以及吡咯類化合物的方法。該方法在合成咔唑類化合物時(shí),采用“一鍋兩步”,使用KI/I2作為促進(jìn)劑,以廉價(jià)易得的芳香胺作為氮芳基的來源,合成一系列中等至良好產(chǎn)率的2,6-二取代-9-芳基咔唑。同時(shí),KI單獨(dú)存在時(shí),以苯胺和苯乙酮為原料合成一系列1,2,4-三芳基吡咯。該方法以廉價(jià)易得的芳香胺與環(huán)己酮或苯乙酮為原料,為合成非對稱的N-芳基咔唑或吡咯提供了一條新途徑。
[Abstract]:Carbazole compounds are a kind of important organic heterocyclic compounds, which are widely used in the fields of medicine, dyes and organic optoelectronic materials. The development of efficient green carbazole synthesis method is one of the research hotspots in organic synthesis. Cyclohexanone compounds with low cost and easy to get non-aromatic can be used as aromatization by "dehydrogenation" of cyclohexanone. For potential aryl sources, And has been successfully used in organic synthesis. In photovoltaic functional materials and drug synthesis, heavy metal contamination and residue is one of the problems that must be considered. Using cheap and easily available cyclohexanone as aryl source to construct carbazole skeleton without transition metal participation can provide a new environmentally friendly approach. In this thesis, cyclohexanone was synthesized from cyclohexanone under the catalysis of transition metal. A series of asymmetric N-aryl carbazole compounds. The main contents of this study are as follows: 1. The synthesis of asymmetric N-aryl carbazole from phenylurea compounds and cyclohexanone compounds without transition metal catalysis was developed. Method. The method does not require the use of transition metal catalysts, The carbazole skeleton all the atoms except nitrogen come from non-aromatic cyclohexanone. Potassium iodide and simple iodine act as accelerators to promote the conversion of the reaction. The reaction provides an efficient green synthesis pathway for the synthesis of asymmetric N-aryl carbazole, and develops a class of aniline compounds with cyclohexanone or acetophenone compounds. A method for forming carbazole and pyrrole compounds. In the synthesis of carbazole compounds, Using "one pot and two steps", using KI/I2 as accelerator, using cheap and easily available aromatic amine as the source of nitrogen aryl, a series of 2C6-disubstituted -9-aryl carbazoles with medium to good yield were synthesized. Using aniline and acetophenone as raw materials, a series of 1'2'2'4- triarylpyrrole were synthesized. This method provides a new way for the synthesis of asymmetric N-aryl carbazole or pyrrole by using cheap and easily available aromatic amine and cyclohexanone or acetophenone as raw materials.
【學(xué)位授予單位】：湘潭大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2017
【分類號】：O626

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