Citation: 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. doi: 10.11944/j.issn.1000-0518.2018.06.170214 shu

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

WANG Qiang ^a,, ,
ZHAO Xinping ^b

a.
College of Chemistry and Chemical Engineering, He'nan Polytechnic University, Jiaozuo, He'nan 454000, China
b.
Hospital of Henan Polytechnic University, He'nan Polytechnic University, Jiaozuo, He'nan 454000, China

Corresponding author: WANG Qiang, wangqiang@hpu.edu.cn
Received Date: 19 June 2017
Revised Date: 21 July 2017
Accepted Date: 7 September 2017

Fund Project: Supported by Natural Science Research Program from Education Department of He′nan Province(No.14A150048)Natural Science Research Program from Education Department of He′nan Province 14A150048

Figures(2)

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.
- hydroxyisophthalate,
- allenic ketones,
- acetonedicarboxylate,
- cascade reaction
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