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

D'Oca, Caroline R. M.; Naciuk, Fabrício Fredo; Silva, Jéssica C.; Guedes, Esthéfani P.; Moro, Celso Camilo; D’Oca, Marcelo Gonçalves Montes; Santos, Leonardo S.; Natchigall, Fabiane M.; Russowsky, Dennis

doi:10.5935/0103-5053.20160175

Cited by 7 publications

(5 citation statements)

References 30 publications

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“…Schemes 1-4 outline the synthetic pathways used to obtain compounds 1-13. The starting materials 2-chloro or 2-keto 3-formylquinoline 1 were prepared according to the reported method [43]. The reactivity of 1 towards some active methylene compounds was discussed.…”

Section: Chemistrymentioning

confidence: 99%

Carboxamide appended quinoline moieties as potential anti-proliferative agents, apoptotic inducers and Pim-1 kinase inhibitors

et al. 2021

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The targeted approach of protein kinases (PKs), as PKs are the main regulators of cell survival and proliferation, has been a promising strategy for treatments for cancer. Here we analyze the potential of quinoline-carboximide derivatives for four cell lines: MCF-7, CACO, HepG-2 and HCT-116 as anticancer agents. 3e, 4b, 11b and 13d derivatives showed good anti-proliferative activities in comparison to the reference standard Doxorubicin, against the four cell lines tested. They have been chosen for further studies. First of all, the IC50 value surveys were carried out to ensure the protection of our hits and demonstrate that the cytotoxic effect (IC50 > 113 μM) is highly selective on normal human cells (WI-38). Secondly, apoptosis was accomplished by down-regulation of Bcl-2 and up-regulation of BAX and Caspase-3 by these active compounds. Also, the Pim-1 inhibitory activity of the active hybrids was done, which indicate that compound 3e was the most active with percentage of inhibition 82.27% and IC50 equal 0.11 when compaired to SGI-1776 as a reference standered. In addition, the in silico assessment of ADME properties, all of the strongest compounds are orally bioavailable without blood brain barrier penetration.

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Section: Chemistrymentioning

confidence: 99%

Carboxamide appended quinoline moieties as potential anti-proliferative agents, apoptotic inducers and Pim-1 kinase inhibitors

et al. 2021

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“…In the second one, 4a can be formed via ketene VIa ( m / z 246 [M + H] + ), which was made from the over decarboxylation of carboxyketene VI . Carboxyketene has been detected as a likely intermediate in the reaction of Meldrum’s acids with nucleophilic reagents in the multicomponent/domino process …”

Section: Resultsmentioning

confidence: 99%

“…Based on NMR and ESI-MS experimental observation, we suggested the mechanistic proposal that has been described in Scheme intermediate in the reaction of Meldrum's acids with nucleophilic reagents in the multicomponent/domino process. 50 Molecular and Crystal Structures of 4f, 4′c, 4′d, 4′g, and 4′s. The molecular structure of the compounds 4f, 4′c, 4′d, 4′g, and 4′s (see Figure 3) is determined by single-crystal X-ray diffraction (XRD) analysis (see Table S1 in the SI).…”

Section: Acs Sustainable Chemistry and Engineeringmentioning

confidence: 99%

Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3H)-ones, Driven under the Umbrella of Sustainable Chemistry

Janković

Stefanović

Petronijević

et al. 2018

ACS Sustainable Chem. Eng.

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The selective synthesis of 5,6-dihydropyrimidin-4(3H)-one scaffold (precursor of dihydrouracil) was a very difficult synthetic challenge that, so far, has not been achieved. For the first time, in this paper, green, selective and high-yields approach to 40 novel 5,6-dihydropyrimidin-4(3H)-ones (DHPMs) by one-pot reaction of aldehydes, Meldrum’s acid and isothioureas under solvent-free conditions, in the presence of water, since an additive is presented. In the majority of cases, introduced methodology gave an unprecedented tautomer-selective fashion toward targeted compounds with excellent tautomeric purity (>99.9%), which reached 100% in few cases. The molecular structure of the five compounds has been determined by X-ray crystallography. In each one of them, very short length for the corresponding N2–C1 bond was noticed, making them especially interesting from a structural standpoint. This experimental fact can imply a highly localized electron π density in this part of each heterocyclic ring. The obtained experimental results, which are determined from NMR and ESI-MS study, indicate that this Biginelli-type reaction smoothly proceeds in a one-pot mode, pointing to the three-step tandem process, proceeding via the Knoevenagel, aza-Michael, and retro-Diels–Alder reactions. The presented strategy also had the following advantages: reduction amount of waste, excellent values of green chemistry metrics (cEF, EcoScale and GCIS), and it is the first eco-friendly strategy toward the DHPMs scaffold.

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“…The final MCR adduct precipitated in the reaction medium and remained adsorbed in the heterogeneous catalysis, whereas in the homogeneous version, product separation was far less laborious. Some multicomponent syntheses, however, may be efficiently conducted under heterogeneous conditions with effective catalytic system recovery [ 196 , 197 , 198 , 199 , 200 , 201 ]. Metal–organic frameworks (MOFs) are, however, active, programmable and recyclable catalysts successfully applied in MCR syntheses, as recently reviewed elsewhere [ 202 , 203 , 204 ].…”

Section: Homogeneous and Heterogeneous Catalysismentioning

confidence: 99%

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

2021

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In this review, we comprehensively describe catalyzed multicomponent reactions (MCRs) and the multiple roles of catalysis combined with key parameters to perform these transformations. Besides improving yields and shortening reaction times, catalysis is vital to achieving greener protocols and to furthering the MCR field of research. Considering that MCRs typically have two or more possible reaction pathways to explain the transformation, catalysis is essential for selecting a reaction route and avoiding byproduct formation. Key parameters, such as temperature, catalyst amounts and reagent quantities, were analyzed. Solvent effects, which are likely the most neglected topic in MCRs, as well as their combined roles with catalysis, are critically discussed. Stereocontrolled MCRs, rarely observed without the presence of a catalytic system, are also presented and discussed in this review. Perspectives on the use of catalytic systems for improved and greener MCRs are finally presented.

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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

Cited by 7 publications

References 30 publications

Carboxamide appended quinoline moieties as potential anti-proliferative agents, apoptotic inducers and Pim-1 kinase inhibitors

Carboxamide appended quinoline moieties as potential anti-proliferative agents, apoptotic inducers and Pim-1 kinase inhibitors

Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3H)-ones, Driven under the Umbrella of Sustainable Chemistry

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

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