本文關(guān)鍵詞： 螺環(huán)化合物 靛紅 多組分反應(yīng) 醋酸 水　出處：《江蘇師范大學(xué)》2017年碩士論文　論文類型：學(xué)位論文

【摘要】：本文以多組分反應(yīng)為基礎(chǔ)合成出多系列的靛紅螺氧化吲哚化合物,反應(yīng)原料易得、價格低廉、反應(yīng)操作簡便。本文研究的多組分反應(yīng)均是在水里面完成的反應(yīng),它們是合成具有分子多樣性的化合物有效途徑,本研究具有反應(yīng)聚合性,原子經(jīng)濟(jì)性和環(huán)境友好的優(yōu)點(diǎn)。第一章主要介紹了多組分反應(yīng)的涵義、歷史及其優(yōu)點(diǎn),合成螺環(huán)化合物的意義和應(yīng)用前景,介紹了以靛紅為基礎(chǔ)原料在其3位合成各種螺環(huán)化合物的研究進(jìn)展,簡述了近幾年在水相中的有機(jī)合成的研究。第二章研究了以3-氨基-1-苯基-1H-吡唑-5(4H)-酮、靛紅及(取代)二苯乙酮為底物,以醋酸為催化劑,水作為溶劑,簡單高效的合成出一系列的吡唑并吡啶螺氧化吲哚衍生物。避免了使用有機(jī)溶劑,符合“綠色化學(xué)”的概念。第三章研究了在水中以茚酮及萘酮、靛紅和3-氨基-1-苯基-1H-吡唑-5(4H)-酮為原料用醋酸催化一鍋法合成茚并雜環(huán)及苯并喹啉螺氧化吲哚衍生物,進(jìn)一步豐富了茚并雜環(huán)及喹啉化合物庫。第四章研究了以水作為溶劑,在醋酸的催化下,以靛紅、3-氨基-1-苯基-1H-吡唑-5(4H)-酮和單環(huán)酮或雜環(huán)酮為原料合成了一系列含吡唑環(huán)的螺氧化吲哚衍生物,反應(yīng)條件溫和,操作簡單,產(chǎn)率高。第五章研究了以靛紅、氨基吡唑類化合物和β-環(huán)二酮為起始原料,以水為溶劑在醋酸的催化下一鍋法合成出了吡唑并喹啉及吡唑并吡啶螺氧化吲哚化合物,該反應(yīng)提供了一條快速、簡便、經(jīng)濟(jì)、環(huán)保的合成途徑。所有產(chǎn)物結(jié)構(gòu)均經(jīng)過核磁共振氫譜和碳譜、紅外光譜、高分辨質(zhì)譜表征,并對這些化合物的合成提出了可能的反應(yīng)機(jī)理。實(shí)驗(yàn)研究表明,在水相中的多組分反應(yīng)合成吲哚螺環(huán)化合物是一條重要的途徑,而靛紅則是合成螺環(huán)化合物的重要試劑。本研究具有原子經(jīng)濟(jì)性高、無毒性、環(huán)境友好、條件溫和、產(chǎn)率高等優(yōu)點(diǎn)。
[Abstract]:On the basis of multicomponent reaction, a series of indole compounds were synthesized. The raw materials are easy to get, the price is low and the reaction is easy to operate. The multicomponent reactions studied in this paper are all completed in water. They are effective ways to synthesize compounds with molecular diversity. This study has the advantages of reactive polymerization, atomic economy and environmental friendliness. Chapter 1 mainly introduces the meaning, history and advantages of multicomponent reactions. The significance and application prospect of the synthesis of spirocyclic compounds are reviewed. The research progress in the synthesis of various spirocyclic compounds based on indirubin at its 3 position is introduced. The study of organic synthesis in aqueous phase in recent years is reviewed. In chapter 2, 3Amino-1-phenyl-1H-pyrazole-4Hoxone, indirubin and (substituted) diacetophenone are used as substrates. Using acetic acid as catalyst and water as solvent, a series of pyrazolopyridine spiroxide indole derivatives were synthesized in a simple and efficient way, avoiding the use of organic solvents. In accordance with the concept of "green chemistry". In chapter 3, indene and naphthone in water were studied. Indolein and 3-amino-1-phenyl-1-H-pyrazolone were used as raw materials to synthesize indolein and benzoquinoline spirooxidated indole derivatives in one pot with acetic acid. In chapter 4th, water was used as solvent, and indirubin was used as catalyst under the catalysis of acetic acid. A series of spiroxyindole derivatives containing pyrazole ring were synthesized from 3-amino-1-phenyl -1H-pyrazole-4Hzolidone and monocyclic ketones or heterocyclic ketones. The reaction conditions were mild and the operation was simple. In chapter 5th, the raw materials of indirubin, aminopyrazole and 尾 -cyclodione were studied. Pyrazolyl quinoline and pyrazopyridine spiroxide indoles were synthesized by one-pot method in the presence of acetic acid with water as solvent. The reaction provides a rapid, simple and economical reaction. All the products were characterized by nuclear magnetic resonance (NMR) and carbon spectroscopy (NMR), infrared spectroscopy (IR) and high resolution mass spectrometry (HRMS). The possible reaction mechanism of these compounds was proposed. The synthesis of indole spirocyclic compounds by multicomponent reaction in aqueous phase is an important way, while indirubin is an important reagent for the synthesis of spirocyclic compounds. This study is characterized by high atomic economy, non-toxicity and environmental friendliness. Mild conditions, high yield and other advantages.
【學(xué)位授予單位】：江蘇師范大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2017
【分類號】：O626
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本文編號：1491104