本文選題：喹啉衍生物 + AMBH反應(yīng)��； 參考：《浙江師范大學(xué)》2016年碩士論文

【摘要】：喹啉衍生物是一類十分重要的氮雜環(huán)化合物,在自然界廣泛存在,由于具有重要的生物活性以及在工業(yè)上的廣泛應(yīng)用,使其吸引了大量科學(xué)工作者的注意。本文在綜述了近年來喹啉合成研究的基礎(chǔ)上,從兩方面對(duì)選擇性合成喹啉衍生物進(jìn)行了研究：(1)仲胺調(diào)控化學(xué)選擇性高效合成喹啉并噻吩衍生物及苯并噻嗪衍生物；(2)奎寧衍生物調(diào)控非對(duì)映選擇性合成具有光學(xué)活性的喹啉并硫吡喃衍生物。本課題首先實(shí)現(xiàn)了鄰異硫氰酸酯肉桂醛和仲胺無催化劑、綠色、高效的串聯(lián)反應(yīng),得到苯并噻嗪類化合物,隨后發(fā)現(xiàn)L-脯氨酸可以催化鄰異硫氰酸酯肉桂醛和溴代試劑的Aza-MBH/Alkylation/Aldol串聯(lián)反應(yīng),選擇性生成喹啉并噻吩或喹啉并二氫噻吩類化合物。通過單晶衍射數(shù)據(jù)分析,確定了產(chǎn)物分子的結(jié)構(gòu)。本課題利用異硫氰酸酯肉桂醛通過分子內(nèi)AMBH反應(yīng)芳構(gòu)化得到2-巰基-3-喹啉甲醛,2-巰基-3-喹啉甲醛與硝基烯烴串聯(lián)反應(yīng),合成了具有3個(gè)連續(xù)手性碳的喹啉并硫吡喃類化合物。通過條件優(yōu)化發(fā)現(xiàn)奎寧雙三氟硫脲Ih和脫甲基丁基醚化奎寧Id兩種催化劑能夠分別催化該反應(yīng),得到優(yōu)秀的產(chǎn)率、對(duì)映選擇性和非對(duì)映選擇性,最重要的是使用兩種催化劑得到的產(chǎn)物構(gòu)型不同,是一對(duì)非對(duì)映異構(gòu)體。通過對(duì)單晶培養(yǎng)數(shù)據(jù)分析,確定了兩種產(chǎn)物的絕對(duì)構(gòu)型。
[Abstract]:Quinoline derivatives are a kind of very important nitrogen heterocyclic compounds, which exist widely in nature. Because of their important biological activity and wide application in industry, quinoline derivatives have attracted the attention of a large number of scientists. In this paper, based on a review of recent studies on the synthesis of quinoline, the selective synthesis of quinoline derivatives was studied from two aspects: 1) the chemical selective synthesis of quinoline thiophene derivatives and benzothiazine derivatives by secondary amines. Quinine derivatives regulate the enantioselective synthesis of optically active quinolopyran derivatives. In this paper, a series reaction of o-isothiocyanate cinnamaldehyde and secondary amine without catalyst, green and high efficiency was carried out to obtain benzothiazines. It was subsequently found that L-proline could catalyze the Aza-MBH / Alkylation / Aldol series reaction of o-isothiocyanate cinnamaldehyde and brominated reagent to selectively produce quinolino-thiophene or quinoline dihydrothiophene compounds. The structure of the product was determined by single crystal diffraction data. In this paper, 2-mercapto -3-quinolinaldehyde and nitroolefin were synthesized by aromatization of isothiocyanate cinnamaldehyde through intramolecular AMBH reaction. Quinoline and thiopyran compounds with three continuous chiral carbon were synthesized by tandem reaction of 2-mercapto-3-quinolinaldehyde with nitroolefins. It was found that two catalysts, Quinine bisfluorothiourea Ih and demethylated Ding Ji etherifying QuininId, could catalyze the reaction, and obtain excellent yield, enantioselectivity and non-enantioselectivity. The most important thing is that the products obtained by using the two catalysts have different configurations and are a pair of enantiomers. The absolute configuration of the two products was determined by analyzing the data of single crystal culture.
【學(xué)位授予單位】：浙江師范大學(xué)
【學(xué)位級(jí)別】：碩士
【學(xué)位授予年份】：2016
【分類號(hào)】：O626.323

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本文編號(hào)：2035825