One-pot Synthesis of Highly Functionalizable 3-(Phenylsulfonyl)-2,3-dihydro-4(1<i>H</i>)-quinolinones via a Cu-catalyzed Aza-Michael Addition/Cyclization Reaction

Kang, Seongil; Yoon, Hongju; Lee, Yun-Mi

doi:10.1246/cl.160772

Cited by 7 publications

(3 citation statements)

References 28 publications

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“…However, to date, very few data are available for arylsulfonylquinolins. Kang et al (2016) described a straightforward and mild one-pot method to synthesize 3-(phenylsulfonyl)-2,3-dihydro-4(1H)quinolinones via a Cu-catalyzed aza-Michael addition/base-mediated cyclization reaction. Other researchers (Ivachtchenko et al 2012a,b) have reported new 3-(phenylsulfonyl)quinoline derivatives as serotonin 5-HT receptor antagonists, performed molecular docking studies, and proposed them for preventing and treating central nervous system (CNS) diseases such as psychiatric disorders, schizophrenia, anxiety disorders, and obesity.…”

Section: Chemical Contextmentioning

confidence: 99%

Synthesis, X-ray diffraction study, analysis of intermolecular interactions and molecular docking of ethyl 1-(3-tosylquinolin-4-yl)piperidine-4-carboxylate

et al. 2022

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The title compound, C24H26N2O4S, can be obtained via two synthetic routes. According to our investigations, the most suitable way is by the reaction of ethyl 2-bromoacetate with sodium tosylsulfinate in dry DMF. It was crystallized from methanol into the monoclinic P21/n space group with a single molecule in the asymmetric unit. Hirshfeld surface analysis was performed to define the hydrogen bonds and analysis of the two-dimensional fingerprint plots was used to distinguish the different types of interactions. Two very weak non-classical C—H...O hydrogen bonds were found and the contributions of short contacts to the Hirshfeld surface were determined. Molecules form an isotropic network of intermolecular interactions according to an analysis of the pairwise interaction energies. A molecular docking study evaluated the interactions in the title compound with the active centers of macromolecules of bacterial targets (Staphylococcus aureus DNA Gyrase PDB ID: 2XCR, Mycobacterium tuberculosis topoisomerase II PDB ID: 5BTL, Streptococcus pneumoniae topoisomerase IV PDB ID: 4KPF) and revealed high affinity towards them that exceeded the reference antibiotics of the fluoroquinolone group.

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Section: Chemical Contextmentioning

confidence: 99%

Synthesis, X-ray diffraction study, analysis of intermolecular interactions and molecular docking of ethyl 1-(3-tosylquinolin-4-yl)piperidine-4-carboxylate

et al. 2022

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“…In turn, diversely substituted quinoline-3-sulfones are available through a range of synthetic methodologies suggested recently. Cyclization strategies [35][36][37][38][39][40][41][42][43][44][45] as well as cycloaddition/cyclocondensation techniques [46][47][48][49][50][51] represent those with heteroring construction. Alternative approaches rely on a peripheral modification of various substrates, such as 3-bromoquinolines [52][53][54][55], quinoline-3-boronic acids [56], and diazonium salts [57].…”

Section: Introductionmentioning

confidence: 99%

Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones

Malkova¹,

Bubyrev²,

Kalinin³

et al. 2023

Beilstein J. Org. Chem.

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Quinoline-based sulfonyl derivatives, and especially sulfonamides, are relevant and promising structures for drug design. We have developed a new convenient protocol for the synthesis of 3-sulfonyl-substituted quinolines (sulfonamides and sulfones). The approach is based on a Knoevenagel condensation/aza-Wittig reaction cascade involving o-azidobenzaldehydes and ketosulfonamides or ketosulfones as key building blocks. The protocol is appropriate for both ketosulfonyl reagents and α-sulfonyl-substituted alkyl acetates providing the target quinoline derivatives in good to excellent yields.

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“…Recently, we described an efficient and mild catalytic conjugate addition of (hetero)aromatic amines to α,β-unsaturated olefins in the presence of a Cu catalyst based on an electron-donating Lewis base ligand. This reaction afforded versatile β-amino nitriles, β-amino sulfones, and β-amino carbonyl compounds with high efficiency and selectivity . However, most of the substrate scopes were limited to terminal olefins bearing a nitrile and sulfonyl group.…”

Section: Introductionmentioning

confidence: 99%

Copper-Catalyzed Aza-Michael Addition of 2-Aminobenzoate to β-Substituted α,β-Unsaturated Ketones: One-Pot Synthesis of 3-Carbonyl-2-Substituted Quinolin-4(1H)-ones

et al. 2018

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We present a new and straightforward one-pot process for the synthesis of 3-carbonyl-4-quinolone derivatives through highly efficient Cu-catalyzed aza-Michael addition of 2-aminobenzoates to β-substituted α,β-unsaturated ketones/cyclization/mild oxidation reactions. A broad range of new versatile 3-carbonyl-quinolin-4(1H)-ones is prepared from readily available chemicals under mild reaction conditions with short reaction times, producing good to excellent yields (up to 99%).

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One-pot Synthesis of Highly Functionalizable 3-(Phenylsulfonyl)-2,3-dihydro-4(1H)-quinolinones via a Cu-catalyzed Aza-Michael Addition/Cyclization Reaction

Cited by 7 publications

References 28 publications

Synthesis, X-ray diffraction study, analysis of intermolecular interactions and molecular docking of ethyl 1-(3-tosylquinolin-4-yl)piperidine-4-carboxylate

Synthesis, X-ray diffraction study, analysis of intermolecular interactions and molecular docking of ethyl 1-(3-tosylquinolin-4-yl)piperidine-4-carboxylate

Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones

Copper-Catalyzed Aza-Michael Addition of 2-Aminobenzoate to β-Substituted α,β-Unsaturated Ketones: One-Pot Synthesis of 3-Carbonyl-2-Substituted Quinolin-4(1H)-ones

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