An alternative quinoline synthesis by via Friedländer reaction catalyzed by Yb(OTf)3

Genovese, Salvatore; Epifano, Francesco; Marcotullio, Maria Carla; Pelucchini, Caroline; Curini, Massimo

doi:10.1016/j.tetlet.2011.04.109

Cited by 40 publications

(20 citation statements)

References 47 publications

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“…Acetylacetone (acac) or pentane-2,4-dione is often used as a good precursor in organic synthesis and as a building block of metal-organic complexes [1,2]. Its anion acts as the bidentate ligand and is known to form complexes with many transition metal ions [3][4][5].…”

Section: Resultsmentioning

confidence: 99%

“…Pseudomonas aeruginosa --a Concentration of 30 mg ml -1 of each chemical compound was used for disc diffusion assay X-ray Crystallography Diffraction data for ligand (1) were collected at room temperature by the x-scan technique on an Agilent Technologies SuperNova four-circle diffractometer with Atlas CCD detector [27], equipped with microfocus CuK a radiation source (k = 1.54178 Å ), while for the complex (2) on an Agilent Technologies Xcalibur four-circle diffractometer with Eos CCD detector [27] and graphite-monochromated MoK a radiation (k = 0.71069 Å ). The data were corrected for Lorentz-polarization as well as for absorption effects [27].…”

Section: Staphylococcus Aureus 14 12mentioning

confidence: 99%

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Synthesis, Antibacterial Studies and Crystal Structures of Tridentate Schiff Base Ligand and It’s Cobalt(III) Complex

et al. 2012

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The crystal structures of 4-[(2-hydroxyphenyl) imino]-2-pentanone (H 2 hpac, 1) and its cobalt(III) complex [Co III (hpac)py 3 ] ? ÁPF 6 -(2) have been determined by X-ray diffraction. The ligand 1 crystallizes in orthorhombic chiral P2 1 2 1 2 1 space group, with a = 8.8405(4) Å , b = 10.5349(8) Å , c = 11.2292)7( Å ), and the complex 2-in the centrosymmetric monoclinic P2/n space group, with a = 16.496(5) Å , b = 10.171(2) Å , c = 16.646(5) Å , and b = 95.53(3)°. In the ligand molecule quite strong intramolecular hydrogen bond closes six-membered ring. The bond length pattern within this ring suggests the significant conjugation and the structure might be therefore regarded as the intermediate between keto-enamine and zwitterionic forms, and the intramolecular hydrogen bond falls into category of resonance-assisted hydrogen bonds. In turn, intermolecular O-HÁÁÁO hydrogen bonds connect the molecules of the ligand into infinite chains along [100] direction. In the complex, the Co(III) ion is hexa-coordinated, by two oxygen and one nitrogen atoms of the doubly-deprotonated ligand 1 and by three nitrogen atoms from three pyridine ligands. The coordination polyhedron is close to a slightly distorted octahedron. The in vitro antimicrobial activity of the Schiff base ligand and its corresponding complex have been tested against human pathogenic bacterias such as Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Escherichia coli.Keywords Schiff base Á Tridentate ligands Á Co complex Á Hydrogen bonds Á Biological activity Results and DiscussionAcetylacetone (acac) or pentane-2,4-dione is often used as a good precursor in organic synthesis and as a building block of metal-organic complexes [1,2]. Its anion acts as the bidentate ligand and is known to form complexes with many transition metal ions [3][4][5]. A general method of preparation of such complexes consists in a reaction of a metal ion with acetylacetone in presence of a base which easily separates the proton. Replacement of the ketone functional group by the imine one results in corresponding bidentate Schiff bases, which also proved to be useful ligands. If 2-hydroxy aniline is used as the amine, one can prepare the tridentate ligand. Such a ligand-4-[(2-hydroxyphenyl)imino]-2-pentanone (hereafter referred to as 1), known as H 2 hpac, where H 2 represents the dissociable enolic -OH and hydroxyphenyl protons-has been already prepared and used for making the square-planar mixed-ligand nickel(II) complex with deprotonated H 2 hpac (i.e. hpac), which coordinates through the enolate oxygen, the imine nitrogen and the deprotonated hydroxyphenyl oxygen atoms. Additionally, the neutral N-donor, imidazole, has been used as an ancillary ligand [6]. Such

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Section: Resultsmentioning

confidence: 99%

Section: Staphylococcus Aureus 14 12mentioning

confidence: 99%

Synthesis, Antibacterial Studies and Crystal Structures of Tridentate Schiff Base Ligand and It’s Cobalt(III) Complex

et al. 2012

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“…Such rare earth metals have been found to catalyse different carbon-carbon and carbon-heteroatom bond formation reactions leading to the desired adducts in satisfactory yields by means of a green chemical approach. [16][17][18][19] In the context of our investigations aimed at setting up easy to handle protocols for the synthesis of useful synthons and/or compounds of biological interest employing lanthanide triflates as catalysts, we report in the present paper that 3-carboxycoumarins can be efficiently obtained by Yb(OTf) 3 hydrate catalysed condensation of Meldrum's acid and differently substituted 2-…”

Section: Introductionmentioning

confidence: 91%

Microwave-assisted synthesis of coumarin-3-carboxylic acids under ytterbium triflate catalysis

Fiorito

Genovese

Taddeo

et al. 2015

Tetrahedron Letters

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“…Y(OTf) 3 under solvent free conditions provided the quinoline derivative 5 aa in better yield than Yb(OTf) 3 (Table 1, entries 3-4). [11] According to our previous results on the advantages of NaAuCl 4 · 2H 2 O as an alternative catalyst in sequential amination/annulation reactions, we isolated the quinoline 5 aa in 63% yield by reacting 1 a with 2 a in ethanol at room temperature in the presence of a catalytic amount of the gold(III) salt ( Table 1, entry 5). [12] Remarkably, the desired product 5 aa was obtained in similar yield in refluxing ethanol in the presence of p-toluenesulfonic acid monohydrate (p-TsOH · H 2 O) (0.2 equiv.)…”

Section: Tion; Michael Additions; Sequential Reactionsmentioning

confidence: 99%

Synthesis of Polycyclic Quinolines by Means of Brønsted Acid Mediated Reaction of β‐(2‐Aminophenyl)‐α,β‐Ynones with Ketones

et al. 2019

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An alternative quinoline synthesis by via Friedländer reaction catalyzed by Yb(OTf)3

Cited by 40 publications

References 47 publications

Synthesis, Antibacterial Studies and Crystal Structures of Tridentate Schiff Base Ligand and It’s Cobalt(III) Complex

Synthesis, Antibacterial Studies and Crystal Structures of Tridentate Schiff Base Ligand and It’s Cobalt(III) Complex

Microwave-assisted synthesis of coumarin-3-carboxylic acids under ytterbium triflate catalysis

Synthesis of Polycyclic Quinolines by Means of Brønsted Acid Mediated Reaction of β‐(2‐Aminophenyl)‐α,β‐Ynones with Ketones

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