Highly efficient one-pot three-component Mannich reaction catalyzed by ZnO-nanoparticles in water

Ian, D. Y. T; Dabiri, Minoo; Salehi, Peyman; Torkian, Laleh

doi:10.3998/ark.5550190.0012.b14

Cited by 23 publications

(3 citation statements)

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“…In 2011, MaGee et al reported a rapid and efficient method for the one-pot Mannich reaction of aldehydes, ketones and amines in the presence of ZnO-nanoparticles. 49 Under the optimized procedure, the reaction was carried out with 4-chlorobenzaldehyde, aniline and cyclohexanone using 0.5 mmol ZnO nanoparticles as the catalyst in water at 60 °C to afford the products in high yields ( Scheme 18 ). This procedure was applied to a wide variety of aromatic aldehydes and amines bearing electron-withdrawing and electron-donating groups to offer facile access to β-amino ketones in excellent yields (74–93%) and with anti-selectivity.…”

Section: Zn-catalysed Mannich Reactionsmentioning

confidence: 99%

Recent advances and prospects in the Zn-catalysed Mannich reaction

et al. 2021

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Section: Zn-catalysed Mannich Reactionsmentioning

confidence: 99%

Recent advances and prospects in the Zn-catalysed Mannich reaction

et al. 2021

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“…This reaction produces β-amino carbonyl compounds from three components: an amine, an aldehyde, and an enolizable ketone. β-amino carbonyl compounds, also known as a Mannich bases, are important intermediates for the synthesis of many pharmaceutical and natural products containing nitrogen in their structures (51)(52)(53)(54).…”

Section: Synthetic Derivatives Of Lawsonementioning

confidence: 99%

“…In 2011, Dabiri et al (56) reported the synthesis of lawsone Mannich bases (HL14-33) via reflux heating over 5-7 hours, using water-like solvent and a InCl 3 (indium trichloride) -like catalyst; the results showed yields of 78% to 90%, thus, an easy, efficient and clean method for their production was defined (Table 1). Using the Mannich reaction with lawsone, various amines and substituted benzaldehydes is a good alternative to synthesizing amino derivatives of 2-hydroxy-1,4-naphthoquinone, since these methods have proved to be efficient, environmentally clean and simple, with high atomic economy (51)(52)(53)(54)(55)(56)(57)(58). Furthermore, the synthesized compounds have demonstrated antibacterial (55), antiparasitic (47) and molluscicidal activity (59).…”

Section: Synthetic Derivatives Of Lawsonementioning

confidence: 99%

Naphthoquinones: biological properties and synthesis of lawsone and derivates - a structured review

López

Nery‐Flores

Belmares

et al. 2014

Vitae

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Background: Naphthoquinones are natural pigments that are widely distributed in nature and have important biological activities. Lawsone (2-hydroxy-1,4-naphthoquinone) and its synthetic derivatives, and especially those containing nitrogen, have promising potential for the treatment of different diseases due to their antibacterial, antifungal, antiviral, antitumor and antiparasitic effects, and for pest control via their molluscicidal and insecticidal activities. Their pharmacological activities and mechanisms of action are related to their oxide/reduction and acid/base properties, and can be modulated by directly adding a substituted to the 1,4-naphthoquinone ring. Due to this, naphthoquinones and their derivatives are at the center of multiple areas of research. In this manuscript, we present a structured review of lawsone, a hydroxyl derivative of naphthoquinone, and discuss relevant reports about the chemistry and synthesis of derivatives. Finally, we present the pharmacological activities and mechanism of action reported. Objective: The purpose of this review is to present recent reports from the literature about the chemistry, synthesis and pharmacological properties of lawsone and its amine derivatives. Methods: This structured review presents a discussion about lawsone literature over the last ten years. The most representative studies including those about the chemistry of lawsone, the synthesis of its derivatives, and pharmacological properties were identified and selected. The information has been compiled, organized and presented into logical topics in order to provide a current review for the field of lawsone chemistry. Results: A general overview of the principal aspects of lawsone chemistry, the synthesis of its derivatives and their pharmacological activities and mechanism of action has been obtained. This provides researchers in the area with a framework from which to investigate further. Conclusions: Lawsone and its derivatives have promising potential for treating several diseases due to their antibacterial, antifungal, antiviral, antitumor and antiparasitic effects and have the potential to control pests via their molluscicidal and insecticidal properties. For this reason, it would be of interest to evaluate the synthetic derivatives of this compound for their pharmacologic actions; in the future, synthetic derivatives of lawsone could potentially be used to treat disease and be used as pesticides.

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pH‐Transformed ZnO‐NPs /NaPTS: The First Room‐Temperature Brisk Synthesis of Flavanones in Aqueous Medium

Shinde¹,

Kamble²,

Pore

et al. 2018

ChemistrySelect

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We investigated pH transformed ZnO NPs viz ZnO nanobullets and ZnO nanograins at pH 11 and 12 respectively, synthesized by co‐precipitation method. The structural, morphological, chemical, compositional and optical properties of synthesized ZnO NPs were analysed by using X‐ray diffraction (XRD), Scanning Electron Microscopy (SEM), Energy Dispersive X‐ray Spectroscopy (EDAX) and Ultra‐Violate Visible spectroscopy (UV‐Vis). The Noteworthy feature of ZnO NPs in presence of NaPTS leads a speedy formation of flavanones from the reaction of an aldehyde and o‐hydroxy acetophenone. Thus, it imparted the first room‐temperature brisk synthesis of flavanones in an aqueous medium.

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Highly efficient one-pot three-component Mannich reaction catalyzed by ZnO-nanoparticles in water

Cited by 23 publications

References 13 publications

Recent advances and prospects in the Zn-catalysed Mannich reaction

Recent advances and prospects in the Zn-catalysed Mannich reaction

Naphthoquinones: biological properties and synthesis of lawsone and derivates - a structured review

pH‐Transformed ZnO‐NPs /NaPTS: The First Room‐Temperature Brisk Synthesis of Flavanones in Aqueous Medium

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