有机化学 ›› 2013, Vol. 33 ›› Issue (11): 2334-2340.DOI: 10.6023/cjoc201306004 上一篇    下一篇

研究论文

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   

  1. 怀化学院化学与化学工程系 怀化 418008
  • 收稿日期:2013-06-04 修回日期:2013-07-18 出版日期:2013-11-25 发布日期:2013-07-26
  • 通讯作者: 李元祥 E-mail:hhxyliyuanjun@163.com
  • 基金资助:

    湖南省科技计划(No. 2012NK3098)、湖南省教育厅科学研究(No. 11A092)、怀化市科技计划(No. 2013)资助项目

N-Alkylation and O-Alkylation of Ethyl 4-(4,6-Dimethoxy-pyrimidin-2-yl)-2-oxo-1,2-dihydroquinoline-3-carboxylate

Li Yuanxiang   

  1. Department of Chemistry and Chemical Engineering, Huaihua University, Huaihua 418008, China
  • Received:2013-06-04 Revised:2013-07-18 Online:2013-11-25 Published:2013-07-26
  • Supported by:

    Project supported by the Planned Science and Technology Project of Hunan Province (No. 2012NK3098), the Scientific Research Fund of Hunan Provincial Education Department (No. 11A092) and the Planned Science and Technology Project of Huaihua City (No. 2013).

以卤化物作烃化试剂、NaH作缚酸剂,在NN-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. 烃化产物的结构通过1H 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

Twenty novel N-substitued and O-substitued compounds were prepared starting from ethyl 4-(4, 6-dimethoxy-py-rimidin-2-yl)-2-oxo-1, 2-dihydroquinoline-3-carboxylate. Various halogenated hydrocarbons were used as resource of alkylation 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.

Key words: quinolinone, alkylation, structural characterization