One pot domino reaction accessing γ-nitroesters: synthesis of GABA derivatives

Naciuk, Fabrício Fredo; Vargas, Debora Z.; D'Oca, Caroline R. M.; Moro, Celso Camilo; Russowsky, Dennis

doi:10.1039/c4nj01552e

Cited by 17 publications

(15 citation statements)

References 85 publications

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“…Speculating about the reaction mechanism, we presumed that the alcoholic solvent is able to promote the opening and transesterification of the Meldrum's acid moiety in the Michael adduct initially formed. 25 The adduct 6a was not isolated during the multicomponent process. Thus, we focused our efforts on its isolation and characterization.…”

Section: Resultsmentioning

confidence: 99%

“…We also observed that HT combined with Meldrum's acid resulted in the formation of γ-nitroesters directly. 25 The activity of HT was attributed to the increase in the basicity of this material by the formation of mixed magnesium and aluminium oxides after thermal treatment that we called HT [Calc. ] .…”

Section: Resultsmentioning

confidence: 99%

“…[25][26][27] Thus, the development of multicomponent methodologies permitting the rapid access to this class of compounds is of great interest. To our best knowledge, this tetracomponent synthesis of γ-nitroesters was not reported in the literature.…”

Section: Introductionmentioning

confidence: 99%

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New Multicomponent Reaction for the Direct Synthesis of β-Aryl-γ-nitroesters Promoted by Hydrotalcite-Derived Mixed Oxides as Heterogeneous Catalyst

D'Oca

Naciuk

Silva

et al. 2016

Journal of the Brazilian Chemical Society

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A new approach based on multicomponent/domino combined reactions for the synthesis of γ-nitroesters promoted by a mixed aluminium-magnesium oxides derived from hydrotalcite-like material was developed. Different γ-nitroesters were synthesized in 15-95% yield using Meldrum's acid, aromatic aldehydes, nitromethane and different alcohols as reagents and solvents. The γ-aminobutyric acid derivatives, Phenibut and Baclofen, were prepared in 63 and 61% overall yield, respectively, through a two steps synthetic strategy. A mechanistic pathway was proposed based on the gas chromatography mass spectrometry (GC-MS) and electrospray ionization mass spectrometry (ESI-MS) experiments.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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New Multicomponent Reaction for the Direct Synthesis of β-Aryl-γ-nitroesters Promoted by Hydrotalcite-Derived Mixed Oxides as Heterogeneous Catalyst

D'Oca

Naciuk

Silva

et al. 2016

Journal of the Brazilian Chemical Society

Self Cite

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“…Waste minimization without any side reactions, use of non-toxic and inexpensive catalysts and recyclability of catalyst are other advantageous features of this procedure. Survey over several reaction parameters (solvent, temperature, and time) was reported by Naciuk et al [98] who investigated Michael reaction for the synthesis of γ-aminobutyric acid (GABA). Another study on the Michael additions of 2-methylcyclohexane-1,3-dione, 2-acetylcyclopentanone, and 2-acetylcyclohexanone to methyl vinyl ketone interestingly revealed that Mg/Al molar ratio was strongly related to the catalytic performance, pointing out a nonlinear correlation between the Mg content and catalytic activity [99].…”

Section: 9 X For Peer 10 Of 43mentioning

confidence: 99%

Layered Double Hydroxides: A Toolbox for Chemistry and Biology

et al. 2019

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Layered double hydroxides (LDHs) are an emergent class of biocompatible inorganic lamellar nanomaterials that have attracted significant research interest owing to their high surface-to-volume ratio, the capability to accumulate specific molecules, and the timely release to targets. Their unique properties have been employed for applications in organic catalysis, photocatalysis, sensors, drug delivery, and cell biology. Given the widespread contemporary interest in these topics, time-to-time it urges to review the recent progresses. This review aims to summarize the most recent cutting-edge reports appearing in the last years. It firstly focuses on the application of LDHs as catalysts in relevant chemical reactions and as photocatalysts for organic molecule degradation, water splitting reaction, CO2 conversion, and reduction. Subsequently, the emerging role of these materials in biological applications is discussed, specifically focusing on their use as biosensors, DNA, RNA, and drug delivery, finally elucidating their suitability as contrast agents and for cellular differentiation. Concluding remarks and future prospects deal with future applications of LDHs, encouraging researches in better understanding the fundamental mechanisms involved in catalytic and photocatalytic processes, and the molecular pathways that are activated by the interaction of LDHs with cells in terms of both uptake mechanisms and nanotoxicology effects.

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“…Due to the utility of β-aryl-γ-lactams as key synthetic intermediates for the synthesis of γ-amino acids [17] in conjunction with their biological activity, several methods have been reported for the synthesis of γ-lactams [18,19,20,21,22]; however, it is yet highly desirable to develop convenient and milder protocols for its preparation, especially with various substitution patterns and enantiomerically purity. In this paper, we report an efficient synthesis of a series of β-aryl-γ-lactams and its resolution by derivatization with ( S )-Naproxen.…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of β-Aryl-γ-lactams and Their Resolution with (S)-Naproxen: Preparation of (R)- and (S)-Baclofen

et al. 2015

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Abstract:An efficient synthesis of enantiomerically-pure β-aryl-γ-lactams is described. The principal feature of this synthesis is the practical resolution of β-aryl-γ-lactams with (S)-Naproxen. The procedure is based on the Michael addition of nitromethane to benzylidenemalonates, which was easily obtained, followed by the reduction of the γ-nitroester in the presence of Raney nickel and the subsequent saponification/decarboxylation reaction. The utility of this methodology was highlighted by the preparation of enantiomerically-pure (R)-and (S)-Baclofen hydrochloride.

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One pot domino reaction accessing γ-nitroesters: synthesis of GABA derivatives

Cited by 17 publications

References 85 publications

New Multicomponent Reaction for the Direct Synthesis of β-Aryl-γ-nitroesters Promoted by Hydrotalcite-Derived Mixed Oxides as Heterogeneous Catalyst

New Multicomponent Reaction for the Direct Synthesis of β-Aryl-γ-nitroesters Promoted by Hydrotalcite-Derived Mixed Oxides as Heterogeneous Catalyst

Layered Double Hydroxides: A Toolbox for Chemistry and Biology

Efficient Synthesis of β-Aryl-γ-lactams and Their Resolution with (S)-Naproxen: Preparation of (R)- and (S)-Baclofen

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