Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (3): 667-674.DOI: 10.6023/cjoc201609027 Previous Articles     Next Articles



叶明琰, 邱少中, 殷国栋   

  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 黄石 435002
  • 收稿日期:2016-09-26 修回日期:2016-11-03 发布日期:2016-11-29
  • 通讯作者: 殷国栋,,,
  • 基金资助:


Synthesis of Quinolinone- and Pyridinone-Fused Oxabicyclo[3.3.1]nonanes

Ye Mingyan, Qiu Shaozhong, Yin Guodong   

  1. Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi 435002
  • Received:2016-09-26 Revised:2016-11-03 Published:2016-11-29
  • Contact: 10.6023/cjoc201609027,
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21542009).

An efficient and stereoselective synthesis of quinolinone- and pyridinone-fused 2,8-dioxabicyclo[3.3.1]-nonanes by the reaction of 2-hydroxychalcones with 4-hydroxy-2(1H)-quinolinones/4-hydroxy-2(1H)-pyridinones in refluxing n-PrOH is described. The quinolinone fragment can be converted into the corresponding N-alkylated quinolinones and O-alkylated quinolines by the alkylation reaction. All the unknown compounds are characterized by means of 1H NMR, 13C NMR, IR and HRMS. The structures and configurations of 6-phenyl-2,12-dihydro-1H-6,12-methanobenzo[7,8] [1,3]dioxocino[5,4-c]pyri-din-1-one (3r) and 1-isopropoxy-8-phenyl-14H-8,14-methanobenzo[7,8] [1,3]dioxocino[5,4-c]quinoline (6c) are further confirmed by X-ray single crystal diffraction analysis.

Key words: 4-hydroxy-2(1H)-quinolinone, 4-hydroxy-2(1H)-pyridinone, bicyclo[3.3.1]nonane, alkylation, X-ray structure