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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (10): 1710-1713. 上一篇    下一篇

研究简报

由α-氰基二硫缩烯酮制备多取代喹唑啉酮化合物

刘璇1，史大昕1，唐健红1,2，张奇1，李加荣*,1   

  1. (1北京理工大学化工与环境学院 北京 100081)
    (2华侨大学化工学院 厦门 362021)
  • 收稿日期:2011-01-21 修回日期:2011-04-29 发布日期:2011-05-25
  • 通讯作者: 李加荣 E-mail:jrli@bit.edu.cn

Synthesis of Polysubstituted Quinazolinones from the Continuous Reaction of α-Cyano Disulfide Ketene

Liu Xuan1 Shi Daxin1 Tang Jianhong1,2 Zhang Qi1 Li Jiarong*,1   

  1. (1 School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijjing 100081)
    (2 College of Chemical Engineering, Huaqiao University, Xiamen 362021)
  • Received:2011-01-21 Revised:2011-04-29 Published:2011-05-25
  • Contact: Li JiaRong E-mail:jrli@bit.edu.cn

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以α-氰基乙酸甲酯为起始原料, 经与二硫化碳、碘甲烷反应先得到α-氰基二硫缩烯酮1, 1与苯乙酮2反应得2H-吡喃-2-酮-3-腈化物3, 碱诱导下3再与丙二腈经环转化得到多取代邻氨基芳香腈4, 4与酮5在氢氧化钠催化下环化得到多取代喹唑啉酮目标物6. 这组连续转化合成多取代喹唑啉酮的反应具有原料简便、反应温和等优点.

关键词: α-氰基二硫缩烯酮, 2H-吡喃-2-酮-3-腈化物, 邻氨基芳香二腈, 喹唑啉酮, 连续反应

α-Cyano disulfide ketene 1 obtained from the reaction of α-methyl cyano-acetate, carbon disulfide and methyl iodide, condensated with acetophenone 2 to provide 3-cyano-2H-pyran-2-ketones 3, then ring transformation of 3 and malononitrile under base afforded aromatic o-amino dinitriles 4, and 4 reacted with ketone 5 to give the polysubstituted quinazolinone 6. This continuous reaction for the convenient synthesis of polysubstituted quinazolinone 6 has the follow advantages: simple raw materials, mild reaction condition, and simple operation.

Key words: α-cyano disulfide ketene, 2H-pyran-2-ketone-nitrile, aromatic o-amino dini-trile, quinazolinone, continuous reaction