4-(4,6-二甲氧基嘧啶-2-基)-2-氧代-1,2-二氢喹啉-3-羧酸乙酯的烃化反应有机化学.pdfVIP

DOI: 10.6023/cjoc201306004 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE 4-(4,6-二甲氧基嘧啶-2-基)-2-氧代-1,2-二氢喹啉-3-羧酸乙酯的 烃化反应 李元祥 (怀化学院化学与化学工程系 怀化 418008) 摘要 以卤化物作烃化试剂、NaH 作缚酸剂, 在 N,N-二甲基甲酰胺(DMF)溶剂中室温条件下, 4-(4,6-二甲氧基嘧啶-2- 基)-2-氧代-1,2-二氢喹啉-3-羧酸乙酯经烃化反应同时得到了20 个未见文献报道的N-取代及O-取代新化合物. 烃化产物 1 的结构通过 H NMR, MS, 元素分析, 单晶衍射及 IR 进行了表征. 烃化反应的条件温和, 转化率高达 89%～98%. 其中, 主产物 N-取代产物的收率为 47%～77%, 副产物 O-取代产物的收率为 21%～49%. 关键词 喹啉酮; 烃化反应; 结构表征 N-Alkylation and O-Alkylation of Ethyl 4-(4,6-Dimethoxy- pyrimidin-2-yl)-2-oxo-1,2-dihydroquinoline-3-carboxylate Li, Yuanxiang (Department of Chemistry and Chemical Engineering, Huaihua University, Huaihua 418008, China) Abstract Twenty novel N-substitued and O-substitued compounds were prepared starting from ethyl 4-(4,6-dimethoxy- pyrimidin-2-yl)-2-oxo-1,2-dihydroquinoline-3-carboxylate. Various halogenated hydrocarbons were used as resource of alky- lation and NaH as base in N,N-dimethylformamide (DMF) at room temperature. The structures of alkylation products were confirmed by 1H NMR, IR, MS and elemental analysis. Two isomer structures were further determined by representative X-ray structures of N10 and O10. The alkylation reaction was performed in mild conditions with a total yield of 89%～98%. Among them, the main product N-alkylation was obtained in 47%～77% yield, and O-alkylation was simultaneously obtained in 21%～49% yield by a simple one-pot reaction. Keywords quinolinone; alky