2-(取代哌嗪-1-甲基)-3-喹啉甲酸乙酯及其衍生物的合成、表征及晶体结构.pdfVIP

2009 年第 29 卷 有 机 化 学 Vol. 29, 2009 第 7 期, 1122～1128 Chinese Journal of Organic Chemistry No. 7, 1122～1128 ·研究论文· 2-(取代哌嗪-1- 甲基)-3-喹啉甲酸乙酯及其衍生物的合成、 表征及晶体结构 吴利欢 a,b 杨定乔*,a (a 华南师范大学化学与环境学院 广州 510006) (b 肇庆学院化学化工学院 肇庆 526060) 摘要 以邻硝基苯甲醛为起始原料, 经还原、Friedländer 缩合反应合成 2- 甲基-3-喹啉甲酸乙酯(2), 2 经 N-溴代丁二酰 亚胺(NBS)溴代得到化合物 3, 3 再与 N-取代哌嗪 5a～5p 发生 SN2 亲核取代反应, 合成一系列 2-(取代哌嗪-1- 甲基)-3- 喹啉甲酸乙酯及其衍生物 6a～6p. 它们的结构通过元素分析, IR, 1H NMR, 13C NMR 和 MS 进行了鉴定和表征, 并用 X 射线衍射法测定了化合物 6n 的晶体结构. 关键词 喹啉; 哌嗪; 合成; 晶体结构 Synthesis, Characterization and Single Crystal Structure of Ethyl 2-(Substituted-piperazin-1-ylmethyl)-quinoline-3-carboxylate Derivatives Wu, Lihuana,b Yang, Dingqiao*,a a ( School of Chemistry and Environment, South China Normal University, Guangzhou 510006) (b School of Chemistry and Chemical Engineering, Zhaoqing University, Zhaoqing 526060) Abstract 2-Methyl-quinoline-3-carboxylic acid ethyl ester (2) was prepared by reduction of o-nitrobenzal- dehydebe and Friedländer condensation with o-aminobenzaldehyde, followed by bromination with N-bromosuccinimide (NBS) to give compound 3. The SN2 reaction of compound 3 with N-substituted- piperazine 5a～5p yielded a series of ethyl 2-(substituted-piperazin-1-ylmethyl)-quinoline-3-carboxylate de- rivatives 6a～6p. The structures of the title compounds 6a～6p were characterized by elemental an