Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (12): 3345-3350.DOI: 10.6023/cjoc201806007 Previous Articles     Next Articles



丁晓友, 徐凡   

  1. 苏州大学材料与化学化工学部 苏州 215123
  • 收稿日期:2018-06-06 修回日期:2018-07-30 发布日期:2018-08-23
  • 通讯作者: 徐凡
  • 基金资助:


Ferric Chloride Catalyzed Synthesis of 2,3-Dihydro-benzo[f]chromen-1-one

Ding Xiaoyou, Xu Fan   

  1. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123
  • Received:2018-06-06 Revised:2018-07-30 Published:2018-08-23
  • Contact: 10.6023/cjoc201806007
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21272168).

Aromatic-fused pyran-4-one skeleton exists in many natural and synthetic biologically active materials. An efficient method for the transformation of naphthyl 3-methylcrotonate to 2,3-dihydro-benzo[f]chromen-1-one catalyzed by ferric chloride is described, which provides a practical process to afford this type of biologically important compounds in good yields using commercially available and inexpensive catalyst. A two-step mechanism involving Fries rearrangement and intramolecular hydroalkoxylation is proposed.

Key words: ferric chloride, aromatic-fused pyrone, catalysis, Fries rearrangement, hydroalkoxylation