The Physical and Chemical Properties of Quinoline

Jones, Gurnos

doi:10.1002/9780470187029.ch1

Cited by 6 publications

(3 citation statements)

References 477 publications

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“…The papers related to the nitrobenzopyridines have been reviewed several times (1)(2)(3)(4)(5)(6)(7)(8). Benzo[b]pyridine (quinoline) and benzo[c]pyridine (isoquinoline) are nitrated by means of mixed acid (H2SO4/HNO3).…”

Section: Introductionmentioning

confidence: 99%

Intramolecular Hydrogen Bonding in the Nitrobenzopyridines

Sánchez‐Viesca¹,

Berros²

2007

Heterocyclic Communications

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The available data on the spectroscopy of the nitrobenzopyridines are insufficient, out-dated, and modern theory is missing. A careful study of the 'H-NMR spectra of these compounds revealed the existence of C-H-0-N=0 hydrogen bonds, the hydrogen being at peri position to the nitro group. The existence of these bonds explains the down-field shifts observed in the signals of the involved protons. Spectral data from the naphthalene series and from 1 O-NMR measurements, both involving the nitro group/per/'-hydrogen relation, confirmed our proposal.

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Section: Introductionmentioning

confidence: 99%

Intramolecular Hydrogen Bonding in the Nitrobenzopyridines

Sánchez‐Viesca¹,

Berros²

2007

Heterocyclic Communications

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“…Quinoline ( 1 ) is an aromatic compound first identified from coal tar by Runge in 1834 . About a century later, Späth and Pikl reported it as one of the trace constituents (about 0.003%) of angostura bark ( Cusparia trifoliata ).…”

mentioning

confidence: 99%

“…2 Quinoline ( 1) is an aromatic compound first identified from coal tar by Runge in 1834. 3 About a century later, Spaẗh and Pikl 4 reported it as one of the trace constituents (about 0.003%) of angostura bark (Cusparia trifoliata). Many compounds that have a quinoline-core structure such as quinine 5 and chloroquine 6 are used as active ingredients in pharmaceutical preparations.…”

mentioning

confidence: 99%

Biosynthesis of Quinoline by a Stick Insect

et al. 2021

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The Peruvian stick insect Oreophoetes peruana is the only known animal source for unsubstituted quinoline in nature. When disturbed, these insects discharge a defensive secretion containing quinoline. Analysis of samples obtained from L-[2′,4′,5′,6,′7′-2 H 5 ]tryptophan-fed stick insects demonstrated that the insects convert it to [5,6,7, H 4 ]quinoline by removing the 2′-CH moiety in the indole ring of tryptophan. Analogous experiments using L-[1′-15 N]tryptophan and L-[1′-15 N, 15 NH 2 ]tryptophan showed that the indole-N atom is retained while the α-amino group is eliminated during the biosynthesis. Mass spectra recorded from quinoline derived from [2-13 C 1 ]tryptophan-fed insects indicated that the αcarbon atom of tryptophan is incorporated as the C-2 atom of the quinoline ring.

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Novel Synthetic and Mechanistic Approach of TFA Catalysed Friedländer Synthesis of 2‐Acylquinolines from Symmetrical and Unsymmetrical 1,2‐Diketones with o‐Aminoarylketones

et al. 2016

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In focussing on the reaction mechanism of Friedländer synthesis in the presence of acid catalysts, novel regioselective synthesis of 2‐acetylquinolines from reacting a symmetrical 1,2‐diketone, butan‐2,3‐dione with o‐aminoarylketones was reported. Similar condensation of o‐aminoarylketones with unsymmetrical 1,2‐diketone, pentan‐2,3‐dione leads to the formation of 2‐propanoylquinoline. The proposed reaction mechanism is scrutinized through density functional calculations at B3LYP/6‐311G (d,p) and M06‐2X/6‐311G (d,p) level of theory and also all the relative energy barriers and activation energies of the reaction steps are found to be minimum at above level of theory. Results from theoretical study have further strengthened by FT‐IR, FT‐NMR chemical shifts and structural parameters which were achieved with the same level of theory and the corresponding results were substantiate with experimental observations.

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The Physical and Chemical Properties of Quinoline

Cited by 6 publications

References 477 publications

Intramolecular Hydrogen Bonding in the Nitrobenzopyridines

Intramolecular Hydrogen Bonding in the Nitrobenzopyridines

Biosynthesis of Quinoline by a Stick Insect

Novel Synthetic and Mechanistic Approach of TFA Catalysed Friedländer Synthesis of 2‐Acylquinolines from Symmetrical and Unsymmetrical 1,2‐Diketones with o‐Aminoarylketones

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