Nanostructured Zirconium Pyrophosphate Catalyzed Diastereoselective Synthesis of β-Amino Ketones via One-Pot Three-Component Mannich Reaction
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In this study, ZrP2O7 catalytic nanomaterials were prepared by co-precipitation and polyvinylpyrrolidone assisted methods. These nanomaterials were structurally characterized by XRD, N2 adsorption/desorption, TGA, SEM and TEM microscopy techniques. This study investigated the application of these nanomaterials in the synthesis of various β-amino carbonyls via a one-pot-three-component condensation of aldehydes, ketones and amines. As a result, high efficiency was obtained in a water–ethanol mixed solvent at room temperature. Under the optimized conditions, the catalyst prepared via the PVP assisted method exhibited higher catalytic activity and higher diastereoselectivity when compared to the catalyst prepared by co-precipitation. Moreover, the ZrP2O7 catalysts were easily recovered and reused several times with only a slight loss of activity. At the conclusion of this study, a possible mechanism of the Mannich reaction over ZrP2O7 catalysts was also proposed and discussed.
KeywordsNanocatalyst Zirconium pyrophosphate Diastereoselectivity Mannich reaction β-amino ketones
The financial assistance of the Moroccan Foundation for Advanced Science, Innovation and Research (MAScIR), towards this research is hereby acknowledged.
- 2.Dua R, Shrivastava S, Sonwane SK, Srivastava SK (2011) Pharmacological significance of synthetic heterocycles scaffold: a review. Adv Biol Res 5:120–144Google Scholar
- 4.Blicke FF (1954) The Mannich reaction in Organic reactions. Wiley Online Library,Google Scholar
- 5.Trmontini A, Angiolini L (1994) Mannich bases: chemistry and uses. CRC press Inc, Boca RatonGoogle Scholar
- 7.Kleinman EF (1991) In comprehensive organic synthesis. Pergamon Press, OxfordGoogle Scholar
- 19.Vadivel P, Maheswari CS, Lalitha A (2013) Synthesis of β-amino carbonyl compounds via Mannich reaction using sulfated MCM-41. Int J Innov Technol Explor Eng 2:267–270Google Scholar
- 22.Magee DI, Dabiri M, Salehi P, Torkian L (2011) Highly efficient one-pot three-component Mannich reaction catalyzed by ZnO-nanoparticles in water. Arkivoc 11:156–164Google Scholar
- 23.Nagrik DM, Ambhore DM, Gawande MB (2010) One-pot preparation of β–amino carbonyl compounds by Mannich reaction using MgO/ZrO2 as effective and reusable catalyst. Int J Chem 2:98–101Google Scholar
- 34.Inoue S, Nobuyuki O (1998) Stationary phase material chromatography, U.S. Patent 5.728.463Google Scholar
- 53.Boumoud B, Zetchi A, Boumoud T, Debache A (2012) SiO2-OSbCl2 as highly effective and reusable heterogeneous catalyst for Mannich condensation in solvent or under solvent-free conditions. J Chem Pharm Res 4:2517–2521Google Scholar