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

doi:10.11944/j.issn.1000-0518.2015.12.150165

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (12): 1371-1378.DOI: 10.11944/j.issn.1000-0518.2015.12.150165

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

LYU Chengwei(),LIU Yanhang,WANG Jiajing,ZHOU Xiaoxia

Shcool of Chemistry and Chemical Engineering,Liaoning Normal University,Dalian,Liaoning 116029,China

Received:2015-05-11 Accepted:2015-08-20 Published:2015-12-01 Online:2015-12-01
Contact: LYU Chengwei
Supported by:
Supported by the National Natural Science Foundation of China(No.21403100), the Doctoral Scientific Research Foundation of Liaoning Province(No.20141100)

Abstract

Abstract:

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.

Key words: three-component reaction, Yonemitsu condensation, potassium dihydrogen phosphate, β-indole derivatives, synthesis

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.

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

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