α-一溴代芳杂环乙酮论文：α-溴代芳杂环乙酮与取代哌啶的c-n亲核取代反应.doc

α-一溴代芳杂环乙酮论文：α-溴代芳（杂）环乙酮与取代哌啶的C-N亲核取代反应 【中文摘要】芳杂环化合物是重要的医药、农药等精细化工产品的中间体,特别在制药领域有着广泛的应用,因而构建功能结构的哌啶化合物已经引起了人们的广泛关注。基于这样的背景,本论文主要以α-溴代芳杂环乙酮和取代哌啶盐酸盐为底物,经C-N亲核取代反应制备新型芳杂环乙酰基取代的哌啶类化合物。实验首先用溴代试剂—过溴四丁基溴化铵合成α-一溴代芳杂环乙酮;其次根据文献经过C-O亲核取代合成取代哌啶的盐酸盐。然后以这两种新制备的中间体作为反应底物,经C-N亲核取代反应合成具有广泛药用价值的芳杂环乙酰基取代的哌啶类化合物。实验中,考查了不同的原料配比、碱、溶剂和温度对反应的影响,得到较优的反应条件,并在较优的反应条件下,改变原料的取代基进行反应,合成1--2-(2’-噻吩基)乙酮等10种双取代的哌啶类衍生物,并通过NMR,MS和IR对目标产物结构进行了表征。 【英文摘要】Aromatic heterocyclic compounds are a class of important fine chemical intermediates for the medicines and agricultural chemicals, and were especially applied widely in the pharmaceutical field. Accordingly, great attention has been paid to the construction of functionalized piperidine compounds. Herein, the C-N nucleophilic substitution reaction was carried out usingα-bromo-aromatic heteroethanone and substituted piperidine as the substrate. First, 2-bromo-1-(thiophen-2-yl)ethanone was synthesized by bromination of aromatic heteroethanone using tetrabutylammo- nium tribromides as brominating agent. Secondly according to the literature,the replaced piperidine hydrochloride was synthesised by the C-O nucleophilic substitution. And then, with the two new preparation intermediates as a reaction to the substrate, the C-N nucleophilic substitution reaction ofα-bromo-aromatic hetero- ethanone and substituted piperidine to offer the corresponding piperidine derivatives. In this experiment, molar ratio, base, solvent and temperature was investigated to establish the optimum reaction conditions. The 2-[4-(Benzothiazol-2-yloxy)-piperidin-1-yl]-1- thiophen-2-yl-ethanone etc 10 species double replaced piperidine kind of derivatives were obtained in yield of 73.7% under optimized condition. The structure of the target product was characterized by MS, NMR, and IR. 【关键词】α-一溴代芳杂环乙酮 C-O亲核取代反应 哌啶 C-N亲核取代反应 【英文关键词】α-bromo heterocyclic ethanone the C-O nucleophilic substitution reaction piperidine the C-N nucleophilic substitution reaction 【备注】索购全文在线加好友：1