Gold-catalyzed addition reaction between creatinine and isatin: A sustainable and green chemistry approach for the diastereoselective synthesis of 3-substituted-3-hydroxyisatins

doi:10.1016/S1872-2067(17)62812-2

Abstract

Abstract:

The aldolization of various isatins with creatinine under gold catalysis in water has been developed. The reaction is operationally simple as the products can be isolated by simple filtration without requiring tedious solvent extraction and column chromatographic techniques. The generality of this methodology is showcased through the reactions of a wide range of isatin derivatives with creatinine to afford the respective aldol products in excellent yields with complete syn-selectivity. The scope of this chemistry is further extended to a tandem reaction involving isatins, creatinine and malononitrile to afford multicomponent products in excellent yields with complete anti-selectivity. The antioxidant potency of the synthesized compound was assessed by a spectrophotometric method, which revealed that three compounds containing halogen atoms (2c, 2d and 2e) were the most active compared with the standard.

Key words: Creatinine, Gold catalysis, Green chemistry, Diastereoselectivity, Antioxidant

K. Parthasarathy, T. Ponpandian, C. Praveen. Gold-catalyzed addition reaction between creatinine and isatin: A sustainable and green chemistry approach for the diastereoselective synthesis of 3-substituted-3-hydroxyisatins[J]. Chinese Journal of Catalysis, 2017, 38(5): 775-783.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(17)62812-2

https://www.cjcatal.com/EN/Y2017/V38/I5/775

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