Chinese Journal of Applied Chemistry ›› 2018, Vol. 35 ›› Issue (6): 645-651.DOI: 10.11944/j.issn.1000-0518.2018.06.170214

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Synthesis of Functionalized 2-Hydroxyisophthalate via the Cascade Reactions of Allenic Ketones with Acetonedicarboxylate

WANG Qianga*(),ZHAO Xinpingb   

  1. aCollege of Chemistry and Chemical Engineering;
    bHospital of Henan Polytechnic University,He'nan Polytechnic University,Jiaozuo,He'nan 454000,China;
  • Received:2017-06-19 Accepted:2017-09-07 Published:2018-06-01 Online:2018-05-28
  • Contact: WANG Qiang
  • Supported by:
    Supported by Natural Science Research Program from Education Department of He'nan Province(No.14A150048).

Abstract:

A novel methodology for the synthesis of 2-hydroxyisophthalates through cascade reactions of 1,2-allenic ketones with ethyl acetonedicarboxylate using K2CO3 as the promoter under extremely mild conditions has been developed. Under optimal reaction conditions, a series of 2-hydroxyisophthalates derivatives were obtained with 73%~85% yield. The formation of the title compounds involves firstly a Michael addition of active methylene compounds and allenic ketone followed by its intramolecular condensation. Notable features of this protocol include simple starting materials, high yield, and easiness of handling.

Key words: hydroxyisophthalate, allenic ketones, acetonedicarboxylate, cascade reaction