Synthesis, spectroscopy and computational studies of selected hydroxyquinoline carboxylic acids and their selected fluoro-, thio-, and dithioanalogues

Nycz, Jacek E.; Malecki, Grzegorz

doi:10.1016/j.molstruc.2012.08.009

Cited by 15 publications

(13 citation statements)

References 28 publications

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“…complex was synthesized according to the literature method [18]. 8-Hydroxy-2-methylquinoline-7-carboxylic acid (MequinCOO), 8-hydroxy-2,5-dimethylquinoline-7-carboxylic acid (2,5-Mequin-COO) and 5-chloro-8-hydroxy-2-methylquinoline-7-carboxylic acid (2-Me-5-ClquinCOO) were synthesized according to procedures described in the literature [19,20].…”

Section: Introductionmentioning

confidence: 99%

Phosphorescent emissions of phosphine copper(I) complexes bearing 8-hydroxyquinoline carboxylic acid analogue ligands

Małecki

Łakomska

Maroń

et al. 2015

Journal of Luminescence

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Section: Introductionmentioning

confidence: 99%

Phosphorescent emissions of phosphine copper(I) complexes bearing 8-hydroxyquinoline carboxylic acid analogue ligands

Małecki

Łakomska

Maroń

et al. 2015

Journal of Luminescence

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“…The synthesis of quinolines 3c , 3d, and 4a followed our procedure described in the literature [ 17 ].…”

Section: Methodsmentioning

confidence: 99%

Direct Amination of Nitroquinoline Derivatives via Nucleophilic Displacement of Aromatic Hydrogen

et al. 2021

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The vicarious nucleophilic substitution of hydrogen (VNS) reaction in electron-deficient nitroquinolines was studied. Properties of all new products have been characterized by several techniques: MS, HRMS, FTIR, GC-MS, electronic absorption spectroscopy, and multinuclear NMR. The structures of 4-chloro-8-nitroquinoline, 8-(tert-butyl)-2-methyl-5-nitroquinoline, 9-(8-nitroquinolin-7-yl)-9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one were determined by single-crystal X-ray diffraction measurements. The 9-(8-nitroquinolin-7-yl)-9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one illustrate the nitro/nitroso conversion within VNS reaction. Additionally, 9-(8-isopropyl-2-((8-isopropyl-2-methyl-5-nitroquinolin-6-yl)methyl)-5-nitrosoquinolin-6-yl)-9H-carbazole is presented as a double VNS product. It is postulated that the potassium counterion interacts with the oxygen on the nitro group, which could influence nucleophile attack in that way.

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“…Method Yield (%) A lone pair of electrons on the hydroxyl oxygen or dimethylamino nitrogen at R 1 position on phenyl ring are conjugated with the π system of quinolone, which increases the electron density at both the C5 and C7 positions on the phenyl ring in all studied quinolines [5,6]. Both positions are suitable for substitution reaction via a SEAr mechanism [6].…”

Section: Compoundmentioning

confidence: 99%

“…The Vilsmeier's reagent and electrophilic dichlorocarbene possess electron-withdrawing (EW) ability. One consequence of the existence of EW groups in electrophiles is a decreased electron density in the newly generated Wheland cations (Scheme 1), which deactivate the N,N-dimethylaniline (or A lone pair of electrons on the hydroxyl oxygen or dimethylamino nitrogen at R 1 position on phenyl ring are conjugated with the π system of quinolone, which increases the electron density at both the C5 and C7 positions on the phenyl ring in all studied quinolines [5,6]. Both positions are suitable for substitution reaction via a S E Ar mechanism [6].…”

Section: Compoundmentioning

confidence: 99%

Synthesis, Electrochemical and Spectroscopic Characterization of Selected Quinolinecarbaldehydes and Their Schiff Base Derivatives

et al. 2020

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A new approach to the synthesis of selected quinolinecarbaldehydes with carbonyl groups located at C5 and/or in C7 positions is presented in this paper in conjunction with spectroscopic characterization of the products. The classical Reimer-Tiemann, Vilsmeier-Haack and Duff aldehyde synthesis methods were compared due to their importance. Computational studies were carried out to explain the preferred selectivity of the presented formylation transformations. A carbene insertion reaction based on Reimer-Tiemann methodology is presented for making 7-bromo-8-hydroxyquinoline-5-carbaldehyde. Additionally, Duff and Vilsmeier-Haack reactions were used in the double formylation of quinoline derivatives and their analogues benzo[h]quinolin-10-ol, 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde, 8-(dimethylamino) quinoline-5,7-dicarbaldehyde and 10-hydroxybenzo[h]quinoline-7,9-dicarbaldehyde. Four Schiff base derivatives of 2,6-diisopropylbenzenamine were prepared from selected quinoline-5-carbaldehydes and quinoline-7-carbaldehyde by an efficient synthesis protocol. Their properties have been characterized by a combination of several techniques: MS, HRMS, GC-MS, FTIR, electronic absorption spectroscopy and multinuclear NMR. The electrochemical properties of 8-hydroxy-quinoline-5-carbaldehyde, 6-(dimethylamino)quinoline-5-carbaldehyde and its methylated derivative were investigated, and a strong correlation between the chemical structure and obtained reduction and oxidation potentials was found. The presence of a methyl group facilitates oxidation. In contrast, the reduction potential of methylated compounds was more negative comparing to non-methylated structure. Calculations of frontier molecular orbitals supported the finding. The structures of 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde and four Schiff bases were determined by single-crystal X-ray diffraction measurements.

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Synthesis, spectroscopy and computational studies of selected hydroxyquinoline carboxylic acids and their selected fluoro-, thio-, and dithioanalogues

Cited by 15 publications

References 28 publications

Phosphorescent emissions of phosphine copper(I) complexes bearing 8-hydroxyquinoline carboxylic acid analogue ligands

Phosphorescent emissions of phosphine copper(I) complexes bearing 8-hydroxyquinoline carboxylic acid analogue ligands

Direct Amination of Nitroquinoline Derivatives via Nucleophilic Displacement of Aromatic Hydrogen

Synthesis, Electrochemical and Spectroscopic Characterization of Selected Quinolinecarbaldehydes and Their Schiff Base Derivatives

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