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Citation: LYU Chengwei, LIU Yanhang, WANG Jiajing, ZHOU Xiaoxia. Potassium Dihydrogen Phosphate Catalyzed Yonemitsu Condensation for Synthesis of 5-[(Indol-3-yl)-arylmethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione Derivatives[J]. Chinese Journal of Applied Chemistry, ;2015, 32(12): 1371-1378. doi: 10.11944/j.issn.1000-0518.2015.12.150165 shu

Potassium Dihydrogen Phosphate Catalyzed Yonemitsu Condensation for Synthesis of 5-[(Indol-3-yl)-arylmethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione Derivatives

1.
Shcool of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029, Chin

Corresponding author: LYU Chengwei,
Received Date: 11 May 2015
Available Online: 20 July 2015
Fund Project: 国家自然科学基金(21403100)资助项目 (21403100)辽宁省博士启动基金(20141100)资助项目 (20141100)

A simple and efficient procedure for the preparation of 5-[(indol-3-yl)-arylmethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives has been developed through the Yonemitsu condensation of indole with Meldrum's acid and aldehyde in the mixed solvent of ethanol and water at room temperature using KH₂PO₄ as an inexpensive,commercially available,and efficient catalyst. The crystal structure of compound 4o was confirmed by X-ray diffraction. This method has the advantages of mild reaction conditions,tolerance to diverse functional groups such as 4-methyl benzaldehyde and 4-methoxy benzaldehyde,and good to excellent yields(48%~98%). Furthermore,some of the products can be facilely obtained by vacuum filtration without further purification. This strategy provides an alternative approach for easy access to useful synthetic β-indole derivatives.
- three-component reaction,
- Yonemitsu condensation,
- potassium dihydrogen phosphate,
- β-indole derivatives,
- synthesis
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