有机化学 ›› 2012, Vol. 32 ›› Issue (08): 1547-1551.DOI: 10.6023/cjoc1112301 上一篇    下一篇

研究简报

萘基薁并[2,1-d]嘧啶-4-胺类衍生物的合成

王道林, 于家懿, 李伟, 崔庆涛, 冯姗姗   

  1. 渤海大学化学化工与食品安全学院 辽宁省功能化合物合成与应用重点实验室 锦州 121003
  • 收稿日期:2011-12-30 修回日期:2012-03-01 发布日期:2012-04-11
  • 通讯作者: 王道林 E-mail:wangdaolin@sina.com.cn
  • 基金资助:

    辽宁省科技厅(No. 2011220022)资助项目.

Synthesis of Naphthylazuleno[2,1-d]pyrimidin-4-amines

Wang Daolin, Yu Jiayi, Li Wei, Cui Qingtao, Feng Shanshan   

  1. Key Laboratory of Synthesis & Application of Functional Compound, College of Chemistry, Chemical Engineering & Food Safety, Bohai University, Jinzhou 121003
  • Received:2011-12-30 Revised:2012-03-01 Published:2012-04-11
  • Supported by:

    Project supported by the Science and Technology Department of Liaoning Province (No. 2011220022).

研究了萘基薁并[2,1-d]嘧啶-4-胺类衍生物的合成方法. 以托酚酮、萘乙酸乙酯、N,N-二甲基甲酰胺二甲缩醛(DMF-DMA)及芳香胺为原料, 依次经过氯代、缩合、环加成、环化反应得到目标产物. 该反应操作简单、条件温和、收率良好. 产物的结构经1H NMR, IR及元素分析等得以证实.

关键词: 薁, 薁并[2,1-d]嘧啶, 萘乙酸乙酯, N,N-二甲基甲酰胺二甲缩醛(DMF-DMA), 芳香胺, 合成

In this paper, a synthetic method for naphthylazuleno[2,1-d]pyrimidin-4-amines was reported, which began from cheap tropolone, ethyl naphthaleneacetate, malononitrile N,N-dimethylformamide dimethyl acetal (DMF-DMA) and anilines, followed by chlorination, condensation, cyclization and then Dimroth rearrangement reaction, to give naphthylazuleno[2,1-d]pyrimidin-4-amines in moderate yields. The structures of synthesized compounds were determined by 1H NMR, IR spectra and elemental analysis. This method provides several advantages such as good yield and simple work-up procedure.

Key words: azulene, azuleno[2,1-d]pyrimidine, ethyl naphthaleneacetate, DMF-DMA, aniline, synthesis