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

doi:10.11944/j.issn.1000-0518.2018.06.170214

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 Qiang^a^*(),ZHAO Xinping^b

^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

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

WANG Qiang,ZHAO Xinping. Synthesis of Functionalized 2-Hydroxyisophthalate via the Cascade Reactions of Allenic Ketones with Acetonedicarboxylate[J]. Chinese Journal of Applied Chemistry, 2018, 35(6): 645-651.

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

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