基于核糖的含氮杂环碳苷化合物的合成研究

发布时间：2018-10-22 17:34

【摘要】：本论文在对氮杂环和碳苷类化合物的研究进展进行概述分析的基础上,以核糖为原料,设计合成出一系列的核糖修饰的氮杂环衍生物,主要的研究内容如下:1.以核糖为原料,与乙酰丙酮糖苷化后,又与不同取代的苯甲醛通过Claisen-Schmidt缩合反应,得到了α,β-不饱和酮碳苷化合物(化合物2-8);再经过溴和双键的加成反应,最后与水合肼、苯肼、盐酸羟胺环合生成吡唑碳苷化合物、N-苯基吡唑碳苷化合物和异恶唑碳苷化合物。2.为了避免使用液溴,对合成路线进一步优化:以核糖为原料,通过上述步骤得到了α,β-不饱和酮碳苷化合物(化合物2-8);然后与对甲苯磺酰肼、苯肼、盐酸羟胺和盐酸氨基脲反应,得到吡唑碳苷化合物、N-苯基吡唑碳苷化合物、异恶唑碳苷化合物和α,β-不饱和氨基脲碳苷类化合物。3.通过以上两种方法合成30种化合物,对所合成的化合物进行核磁、红外以及高分辨质谱的检测确定其结构,30种均为新化合物;推测了几种类型的吡唑碳苷化合物的反应机理。
[Abstract]:In this paper, a series of ribose-modified nitrogen heterocyclic derivatives are designed and synthesized based on the summarization and analysis of the research progress of nitrogen heterocyclic and carbon glycosides. The main research contents are as follows: 1. 伪, 尾 -unsaturated ketone carboside (compound 2-8) was synthesized by Claisen-Schmidt condensation with different substituted benzaldehyde after glycosylation with acetylacetone from ribose, and then by addition reaction of bromine and double bond with hydrazine hydrate and phenylhydrazine. Hydroxylamine hydrochloride cyclization to form pyrazole carboside compounds, N-phenylpyrazole carboside compounds and isooxazole carboside compounds. 2. In order to avoid the use of liquid bromine, the synthesis route was further optimized: 伪, 尾 -unsaturated ketone carboglycosides (compounds 2-8) were obtained from ribose as raw materials, and then reacted with p-toluenesulfonyl hydrazine, phenylhydrazine, hydroxylamine hydrochloride and semicarbazone hydrochloride, Pyrazole carboside, N-phenylpyrazole carboside, isoxazole carboside and 伪, 尾 -unsaturated semicarbazone were obtained. Thirty compounds were synthesized by the above two methods. The structures of the compounds were determined by NMR, IR and high resolution mass spectrometry, and 30 compounds were new compounds. The reaction mechanism of several types of pyrazole carboside compounds was deduced.
【学位授予单位】：郑州大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：R914

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