Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1234-1240.DOI: 10.6023/cjoc202007056 Previous Articles     Next Articles



殷国栋1,*(), 李源1, 范玲1   

  1. 1 湖北师范大学化学化工学院 污染物分析与资源化湖北省重点实验室 湖北黄石 435002
  • 收稿日期:2020-07-24 修回日期:2020-09-30 发布日期:2020-10-22
  • 通讯作者: 殷国栋
  • 基金资助:
    湖北省教育厅重点项目(D20192503); 国家自然科学基金(21542009)

ZrCl4-Catalyzed Synthesis of Pyrimido[4,5-b]quinolin-2,4-(1H,3H)- diones and 11H-Indeno[1,2-b]quinolin-11-ones

Guodong Yin1,*(), Yuan Li1, Ling Fan1   

  1. 1 Hubei Key Laboratory of Pollutant Analysis and Reuse Technology,College of Chemistry and Chemical Engineering,Hubei Normal University,Huangshi, Hubei 435002
  • Received:2020-07-24 Revised:2020-09-30 Published:2020-10-22
  • Contact: Guodong Yin
  • About author:
    * Corresponding author. E-mail:
  • Supported by:
    Educational Commission of Hubei Province(D20192503); National Natural Science Foundation of China(21542009)

Using zirconium tetrachloride as the catalyst, a multicomponent tandem reaction of isatin, 1,3-dimethyl barbituric acid/1,3-indanedione and aliphatic alcohol, effectively gave the corresponding fused-ring compounds pyrimido[4,5-b]quino- lone-2,4-(1H,3H)-diones and 11H-indeno[1,2-b]quinolin-11-ones. The ester group was introduced into these nitrogen-containing molecules. All these newly synthesized compounds were identified by means of 1H NMR, 13C NMR, IR and HRMS. Moreover, ethyl-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimido[4,5-b]quinoline-5-carboxylate (4q) was confirmed by X-ray single crystal diffraction analysis. Owing to the mild reaction conditions and simple easy available starting materials, the method for the preparation of the above two fused-ring skeletons is complementary to the existing methods, which can effectively enrich the corresponding heterocyclic compound library.

Key words: pyrimido[4,5-b]quinolin-2,4-(1H,3H)-dione, 11H-indeno[1,2-b]quinolin-11-one, fused-ring compound, multicomponent reaction, synthesis