2-Hydrazinylquinoline

Najib, Muhd. Hidayat bin; Tan, Ai Ling; Young, David J.; Ng, Seik Weng; Tiekink, Edward R. T.

doi:10.1107/s1600536812026906

Cited by 3 publications

(2 citation statements)

References 8 publications

(9 reference statements)

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“…Synthesis of target compounds (11a-f) was achieved as outlined in (Schemes 1 and 3). The starting material 2-hydrazinylquinoline 1 was synthesized in a high yield from the reaction of hydrazine hydrate with 2-chloroquinoline in refluxing n-butanol, through procedures similar to the previously reported method [25] and its modification [26]. Structure of compound 1 was confirmed by its IR spectrum that revealed presence of two bands at 3282, 3188 cm -1 corresponding to NH groups and two bands at 3042, 1621 cm -1 corresponding aromatic CH and C=N, respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization and Antimicrobial Activity of Some Novel Quinoline Derivatives Bearing Pyrazole and Pyridine Moieties

Amer

El‐Eraky

Mahgoub³

2018

Egypt. J. Chem.

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our efforts were directed towards the synthesis of new heterocyclic compounds containing quinoline ring bearing pyrazole and pyridine moieties with anticipated biological activities. Experimental General All melting points were determined in openglass capillaries and are uncorrected. IR spectra were recorded on a Bruker Vector 22 Germany spectrometer (KBr). 1 HNMR spectra were recorded on Bruker 400 MHz spectrometer using TMS as an internal reference. The Electron Impact mass spectrometry was obtained at 70 eV using Shimadzu QP-2010 Plus mass spectrometer. The reactions were monitored by thin-layer chromatography (TLC) on silica gel F254 aluminum sheets (Merck), and the spots were visualized by UV lamp at 254-365 nm. I N continuation of our interest in synthesis of novel quinoline derivatives with anticipated biological activity, we have synthesized new quinoline derivatives bearing pyrazole and pyridine moieties by formylation of quinoline hydrazones through the Vilsmeier-Haack reaction which is a common method for the synthesis of 4-formyl pyrazoles. Condensation of 2-hydrazinylquinoline 1 with 4-substituted acetophenone gave the corresponding hydrazones 2a-c which in turn underwent the Vilsmeier-Haack reaction in POCl 3 /DMF to furnish the corresponding 4-formyl pyrazole derivatives 3a-c. One-pot reaction of compounds 3a-c with malononitrile and thiophenol or ethyl mercaptan gave the 3,5-pyridine dicarbonitrile derivatives 11a-f. The synthesized derivatives were screened for their antimicrobial activities against Gram negative bacteria, Gram positive bacteria and Fungi. Most of compounds showed excellent antimicrobial activities compared to the reference drugs. All the newly synthesized compounds have been characterized by means of elemental analyses, IR, 1 H NMR and MS.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization and Antimicrobial Activity of Some Novel Quinoline Derivatives Bearing Pyrazole and Pyridine Moieties

Amer

El‐Eraky

Mahgoub³

2018

Egypt. J. Chem.

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“…Lead, one of the earliest known metals, continues to attract interest due to its fascinating coordination chemistry. [1][2][3][4][5][6][7][8][9] Lead can be hypervalent using its 6S 2 orbital and form inorganic clusters. Pb(II) polymeric inorganic clusters show holo and hemi directionality.…”

Section: Introductionmentioning

confidence: 99%

Role of tetrel bonds in the supramolecular architecture of tetranuclear Pb(ii)[LL′thiophene carboxylate] complexes – an experimental and computational study

Darious,

Evangeline,

Perdih

et al. 2024

CrystEngComm

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3,5-Diphenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-5-ol

Najib¹,

Tan²,

Young³

et al. 2012

Acta Cryst E

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In the title compound, C24H19N3O, the pyrazole ring is close to being planar (r.m.s. deviation of the five fitted atoms = 0.062 Å), and each of the N-bound quinoline ring [dihedral angle = 9.90 (7)°] and the C-bound phenyl ring in the 3-position is close to being coplanar [dihedral angle = 8.87 (9)°]. However, the phenyl ring in the 5-position forms a dihedral angle of 72.31 (9)°. The hydroxy group forms an intramolecular hydrogen bond to the quinoline N atom. In the crystal, molecules are connected into supramolecular layers two molecules thick in the bc plane by C—H⋯O and C—H⋯π interactions.

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2-Hydrazinylquinoline

Cited by 3 publications

References 8 publications

Synthesis, Characterization and Antimicrobial Activity of Some Novel Quinoline Derivatives Bearing Pyrazole and Pyridine Moieties

Synthesis, Characterization and Antimicrobial Activity of Some Novel Quinoline Derivatives Bearing Pyrazole and Pyridine Moieties

Role of tetrel bonds in the supramolecular architecture of tetranuclear Pb(ii)[LL′thiophene carboxylate] complexes – an experimental and computational study

3,5-Diphenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-5-ol

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