苯并咪唑化合物和1,2,4-三氮唑化合物的合成研究
发布时间：2018-11-07 20:14
【摘要】：苯并咪唑化合物是一类重要的含氮杂环化合物,普遍存在于天然化合物与合成化合物中,是多种药物的活性结构单元。鉴于苯并咪唑化合物其独特的结构特性、反应活性和生理活性等如此广泛的应用价值以及广阔的市场前景,因此发展一种简便,实用的苯并咪唑化合物的合成方法越来越受到科学家们的关注。在本论文中,我们首次阐述了一种简便的铜盐催化、叠氮化钠参与的快速合成苯并咪唑化合物的方法。该方法具有良好的官能团容忍性、反应条件温和、催化剂廉价易得等优点。其中碘化亚铜引发SNAr反应并辅助后续的单电子转移氧化过程,以及促进随后的脱氮、环化过程,最终生成苯并咪唑化合物。1,2,4-三氮唑化合物也是一类重要的含氮杂环化合物,普遍存在于天然化合物与功能材料中。以1,2,4-三氮唑为核心的化合物,已经在生物和药物领域以及材料科学领域中得到了广泛的应用。同时1,3,5-三芳基取代-1,2,4-三氮唑化合物在太阳能电池、图像传感器、染料激光器和电致发光器件等领域中也有广泛的应用。因此,发展一种高效、简便、温和的制备方法备受科学家们的普遍关注。在本论文中,我们阐述了一种简便、快速有效的以非金属碘为催化剂,过氧化叔丁醇(70%水溶液)为氧化剂,以醛腙和脂肪胺为底物,发生自由基氧化偶联反应,在空气条件下即可高效合成一系列具有重要生物活性的1,3,5-三取代-1,2,4-三氮唑化合物的合成方法。该方法起始原料廉价易得,反应条件温和易控,反应底物范围广泛,官能团容忍性好并且可以轻易扩大至克级,为合成1,3,5-三取代-1,2,4-三氮唑衍生物提供了一种简便高效的方法。同时我们还应用此方法合成了含有1,2,4-三氮唑结构单元的芴类衍生物,并测定了其荧光性能。
[Abstract]:Benzimidazole compounds are a kind of important nitrogen-containing heterocyclic compounds, which are widely found in natural compounds and synthetic compounds, and are active structural units of many kinds of drugs. In view of the unique structural properties of benzimidazole compounds, their wide application value such as reaction activity and physiological activity, and their broad market prospects, they have developed a simple and convenient method for the development of benzimidazole compounds. The practical synthesis of benzimidazole compounds has attracted more and more attention of scientists. In this paper, we first described a simple method for the rapid synthesis of benzimidazole compounds catalyzed by copper salt and with the participation of sodium azide. The method has the advantages of good functional group tolerance, mild reaction conditions and cheap catalyst. Copper iodide initiated the SNAr reaction and assisted in the subsequent single electron transfer oxidation process, and promoted the subsequent denitrification and cyclization process to form benzimidazole compound. 4-triazole compounds are also an important class of nitrogen-containing heterocyclic compounds, which are widely found in natural compounds and functional materials. The compounds with the core of 1C 2N 4-triazole have been widely used in the fields of biology, medicine and material science. At the same time, 1C ~ (3) O _ (5) -triarylsubstituted -1H _ (2) O _ (4) -triazole compounds have been widely used in solar cells, image sensors, dye lasers and electroluminescent devices. Therefore, the development of an efficient, simple and mild preparation method has attracted widespread attention of scientists. In this paper, we described a simple, rapid and effective oxidative coupling reaction of tert butanol peroxide (70% aqueous solution) with nonmetallic iodine as catalyst, aldehyde-hydrazone and aliphatic amine as substrates. A series of important bioactive compounds of 1 ~ (3) O _ (5) -1 ~ (2 +) ~ (2) C _ (2) O _ (4-triazole) can be synthesized efficiently under air conditions. The initial raw material is cheap and easy to obtain, the reaction conditions are mild and easy to control, the reaction substrate is wide, the functional group tolerance is good and can be easily extended to gram class. 4-triazole derivatives provide a simple and efficient method. At the same time, we have synthesized fluorene derivatives containing 1 ~ (2) O ~ (4) -triazole structure unit by using this method, and have determined their fluorescence properties.
【学位授予单位】：浙江理工大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626;O643.36
本文编号：2317452
[Abstract]:Benzimidazole compounds are a kind of important nitrogen-containing heterocyclic compounds, which are widely found in natural compounds and synthetic compounds, and are active structural units of many kinds of drugs. In view of the unique structural properties of benzimidazole compounds, their wide application value such as reaction activity and physiological activity, and their broad market prospects, they have developed a simple and convenient method for the development of benzimidazole compounds. The practical synthesis of benzimidazole compounds has attracted more and more attention of scientists. In this paper, we first described a simple method for the rapid synthesis of benzimidazole compounds catalyzed by copper salt and with the participation of sodium azide. The method has the advantages of good functional group tolerance, mild reaction conditions and cheap catalyst. Copper iodide initiated the SNAr reaction and assisted in the subsequent single electron transfer oxidation process, and promoted the subsequent denitrification and cyclization process to form benzimidazole compound. 4-triazole compounds are also an important class of nitrogen-containing heterocyclic compounds, which are widely found in natural compounds and functional materials. The compounds with the core of 1C 2N 4-triazole have been widely used in the fields of biology, medicine and material science. At the same time, 1C ~ (3) O _ (5) -triarylsubstituted -1H _ (2) O _ (4) -triazole compounds have been widely used in solar cells, image sensors, dye lasers and electroluminescent devices. Therefore, the development of an efficient, simple and mild preparation method has attracted widespread attention of scientists. In this paper, we described a simple, rapid and effective oxidative coupling reaction of tert butanol peroxide (70% aqueous solution) with nonmetallic iodine as catalyst, aldehyde-hydrazone and aliphatic amine as substrates. A series of important bioactive compounds of 1 ~ (3) O _ (5) -1 ~ (2 +) ~ (2) C _ (2) O _ (4-triazole) can be synthesized efficiently under air conditions. The initial raw material is cheap and easy to obtain, the reaction conditions are mild and easy to control, the reaction substrate is wide, the functional group tolerance is good and can be easily extended to gram class. 4-triazole derivatives provide a simple and efficient method. At the same time, we have synthesized fluorene derivatives containing 1 ~ (2) O ~ (4) -triazole structure unit by using this method, and have determined their fluorescence properties.
【学位授予单位】：浙江理工大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626;O643.36
【参考文献】
相关期刊论文 前1条
1 Rahul R.NAGAWADE;Devanand B.SHINDE;;BF_3·OEt_2 Promoted Solvent-free Synthesis of Benzimidazole Derivatives[J];Chinese Chemical Letters;2006年04期
，本文编号：2317452
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