發(fā)布時間：2018-04-18 04:04

  本文選題：可見光 + 吲哚�。� 參考：《淮北師范大學(xué)》2017年碩士論文

【摘要】：吲哚是一種非常重要的含氮雜環(huán)化合物,廣泛存在于天然產(chǎn)物和藥物中,具有重要的生物活性和廣泛的用途,正因為如此,其合成方法一直受到化學(xué)家的關(guān)注。在過去的幾年里,可見光催化在有機(jī)化學(xué)領(lǐng)域取得了很大的突破。最近,可見光促進(jìn)的無光敏化劑的有機(jī)合成反應(yīng)也相繼被報道,并逐漸成為有機(jī)化學(xué)領(lǐng)域中一個熱點。本文主要圍繞可見光促進(jìn)的吲哚環(huán)的構(gòu)建及其官能化反應(yīng)開展了相關(guān)的研究工作,具體如下:1.在可見光照射下,由2-炔基苯胺與二硫醚(二硒醚)合成3-硫基吲哚或3-硒基吲哚化合物的氧化環(huán)化反應(yīng)。該反應(yīng)在室溫,雙氧水的存在下,即可通過一鍋法構(gòu)建吲哚類化合物。值得一提的是,該反應(yīng)在無過渡金屬和光催化劑的條件下,即可以中等以上產(chǎn)率及良好的官能團(tuán)兼容性得到目標(biāo)產(chǎn)物,與傳統(tǒng)合成方法相比,該反應(yīng)體系條件簡單,綠色環(huán)保。2.在溫和的條件下,通過可見光照射,實現(xiàn)了吲哚或N-取代吲哚與苯甲酰甲酸的脫羧偶聯(lián)反應(yīng)。這是一種簡單且有效合成3-�；�吲哚的方法。該反應(yīng)與現(xiàn)有合成3-�；�吲哚的方法相比,具有以下幾個優(yōu)點,例如:使用廉價的,易降解的有機(jī)染料孟加拉玫瑰紅(rose bengal)作為光催化劑;乙醇作為低毒性溶劑;具有高的區(qū)域選擇性和良好的官能團(tuán)兼容性。
[Abstract]:Indole is a very important nitrogen-containing heterocyclic compound, which widely exists in natural products and drugs, and has important biological activity and wide application. Because of this, the synthetic method of indole has been paid much attention by chemists.In the past few years, visible light catalysis has made a great breakthrough in the field of organic chemistry.Recently, the organic synthesis reactions without Guang Min promoted by visible light have been reported one after another, and have gradually become a hot spot in the field of organic chemistry.This paper focuses on the construction and functionalization of visible light-stimulated indole ring, as follows: 1.The oxidative cyclization of 3-thioindole or 3-selenoindole was synthesized from 2-acetylaniline and disulfide (diselenoether) under visible light irradiation.At room temperature and in the presence of hydrogen peroxide, indole compounds can be synthesized by one-pot method.It is worth mentioning that under the condition of no transition metal and photocatalyst, the target product can be obtained with medium yield and good functional group compatibility. Compared with the traditional synthesis method, the reaction system is simple, green and environmentally friendly.Under mild conditions, the decarboxylation of indole or N-substituted indole with benzoyl formic acid was realized by visible light irradiation.This is a simple and effective method for the synthesis of 3-acylated indole.Compared with the existing methods for the synthesis of 3-acylated indole, the reaction has the following advantages: for example, the cheap and easily degradable organic dye, rose rose rose bengal, is used as photocatalyst, and ethanol is used as low toxic solvent.It has high regioselectivity and good functional group compatibility.
【學(xué)位授予單位】：淮北師范大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2017
【分類號】：O626;O644.1

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