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Journal articles on the topic 'Methyl quinoline'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Horta, Pedro, Marta S. C. Henriques, Elisa M. Brás, et al. "On the ordeal of quinolone preparation via cyclisation of aryl-enamines; synthesis and structure of ethyl 6-methyl-7-iodo-4-(3-iodo-4-methylphenoxy)-quinoline-3-carboxylate." Pure and Applied Chemistry 89, no. 6 (2017): 765–80. http://dx.doi.org/10.1515/pac-2016-1119.

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AbstractRecent studies directed to the design of compounds targeting the bc1 protein complex of Plasmodium falciparum, the parasite responsible for most lethal cases of malaria, identified quinolones (4-oxo-quinolines) with low nanomolar inhibitory activity against both the enzyme and infected erythrocytes. The 4-oxo-quinoline 3-ester chemotype emerged as a possible source of potent bc1 inhibitors, prompting us to expand the library of available analogs for SAR studies and subsequent lead optimization. We now report the synthesis and structural characterization of unexpected ethyl 6-methyl-7-i

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2

Portilla, Jaime, Jairo Quiroga, Manuel Nogueras, et al. "Structural comparisons of isomeric series of 7-aryl-benzo[h]pyrazolo[3,4-b]quinolines and 11-aryl-benzo[f]pyrazolo[3,4-b]quinolines." Acta Crystallographica Section B Structural Science 64, no. 1 (2008): 72–83. http://dx.doi.org/10.1107/s0108768107065743.

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The structures of three new 7-aryl-benzo[h]pyrazolo[3,4-b]quinolines, 8-methyl-7-(4-chlorophenyl)-10-phenyl-6,10-dihydro-5H-benzo[h]pyrazolo[3,4-b]quinoline, C27H20ClN3, 8-methyl-7-(3-pyridinyl)-10-phenyl-6,10-dihydro-5H-benzo[b]pyrazolo[3,4-b]quinoline, C26H20N4, and 8-methyl-7-(4-pyridinyl)-10-phenyl-10H-benzo[h]pyrazolo[3,4-b]quinoline, C26H18N4, which is an unexpected oxidation product isolated from the attempted synthesis of 8-methyl-7-(4-pyridinyl)-10-phenyl-6,10-dihydro-5H-benzo[h]pyrazolo[3,4-b]quinoline, and those of three new 11-aryl-benzo[f]pyrazolo[3,4-b]quinolines, 11-(4-methylphe

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3

Schmidt, Alexander, Matthias Baune, Alexander Hepp, Jutta Kösters, and Jens Müller. "Gold(III)-mediated cyclization of 2-hydrazinylquinolines." Zeitschrift für Naturforschung B 71, no. 5 (2016): 527–33. http://dx.doi.org/10.1515/znb-2016-0021.

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AbstractThe Au(III)-mediated oxidative cyclization of a series of 2-hydrazinylquinolines is reported. This intramolecular reaction represents a reliable way towards obtaining various 3H-1,2,4-triazolo[4,3-a]quinolin-10-ium cations. The molecular structures of three of the starting compounds (2-(1-methyl-2-(pyridin-2-ylmethylene)hydrazinyl)quinoline, 2-(1-methyl-2-(thiophen-2-ylmethylene)hydrazinyl)quinoline, 2-((2-methyl-2-(quinolin-2-yl)hydrazono)methyl)aniline) as well as of one cyclized system (3-methyl-1-(pyridin-2-yl)-3H-1,2,4-triazolo[4,3-a]quinolin-10-ium dichloridoaurate(I)) were deter

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4

Elagamey, Abdel Ghani A., Salah Z. Sawllim, Fathy M. A. El-Taweel, and Mohamed H. Elnagdi. "Nitriles in heterocyclic synthesis: Novel syntheses of benzo[b]pyrans, naphtho[1,2-b]pyrans, naphtho[2,1-b]pyrans, pyrano[3,2-h]quinolines and pyrano[3,2-c]quinolines." Collection of Czechoslovak Chemical Communications 53, no. 7 (1988): 1534–38. http://dx.doi.org/10.1135/cccc19881534.

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Benzo[b]pyrans, naphtho[1,2-b]pyrans, naphtho[2,1-b]pyrans, pyrano[3,2-h]quinolines, and pyrano[3,2-c]quinolines were synthesized by the reaction of cinnamonitriles with phenols, naphthols, 8-hydroxyquinoline, and 1-methyl-4-hydroxy-2-quinoline.

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5

Faldu, V. J., P. K. Talpara, N. H. Bhuva, P. R. Vachharajani, and Viresh H. Shah. "Synthesis, Characterization and Biological Evaluation of some Newer 5-[6-Chloro/Fluor/Nitro-2-(p-Chloro/Fluoro/Methyl Phenyl)-Quinolin-4-yl]-1,3,4-Oxadiazole-2-Thiols." International Letters of Chemistry, Physics and Astronomy 25 (January 2014): 26–32. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.25.26.

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Recent study shows that quinolines represent one of the most active classes of compounds possesses wide spectrum biodynamic activities and use as potent therapeutic agents. In present research work, 5-[6-chloro/fluoro/nitro-2-(p-chloro/fluoro/methyl phenyl)-quinolin-4-yl]-1,3,4-oxadiazole-2-thiols have been synthesized by condensation of substituted quinoline-4-carbohydrazides and mixture of carbon disulphide and potassium hydroxide. All of these compounds were screened for their in vitro anti microbial assay against gram (+ve), gram (-ve) bacteria and fungi activity compared with standard dru

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6

Faldu, V. J., P. K. Talpara, N. H. Bhuva, P. R. Vachharajani, and Viresh H. Shah. "Synthesis, Characterization and Biological Evaluation of some Newer 5-[6-Chloro/Fluor/Nitro-2-(p-Chloro/Fluoro/Methyl Phenyl)-Quinolin-4-yl]-1,3,4-Oxadiazole-2-Thiols." International Letters of Chemistry, Physics and Astronomy 25 (January 10, 2014): 26–32. http://dx.doi.org/10.56431/p-vi5cvh.

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Recent study shows that quinolines represent one of the most active classes of compounds possesses wide spectrum biodynamic activities and use as potent therapeutic agents. In present research work, 5-[6-chloro/fluoro/nitro-2-(p-chloro/fluoro/methyl phenyl)-quinolin-4-yl]-1,3,4-oxadiazole-2-thiols have been synthesized by condensation of substituted quinoline-4-carbohydrazides and mixture of carbon disulphide and potassium hydroxide. All of these compounds were screened for their in vitro anti microbial assay against gram (+ve), gram (-ve) bacteria and fungi activity compared with standard dru

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7

Kamal, Ahmed, Abdul Rahim, Sd Riyaz, et al. "Regioselective synthesis, antimicrobial evaluation and theoretical studies of 2-styryl quinolines." Organic & Biomolecular Chemistry 13, no. 5 (2015): 1347–57. http://dx.doi.org/10.1039/c4ob02277g.

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2-Styryl quinolines have been synthesized regioselectively from 2-methyl-quinoline using NaOAc in water acetic acid binary solvents and evaluated for their antibacterial activity against both Gram-positive and Gram-negative strains.

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8

Radini, Ibrahim Ali, Sameh Ramadan El-Gogary, Mohamed Sabri Mostafa, Bander Alnagei, Mohammed Mudarbish, and Shadad Dash. "Ecofriendly and simple synthesis of pyrano[3,2-c]quinolone in water via an efficient one-pot three-component reaction." European Journal of Chemistry 9, no. 1 (2018): 44–48. http://dx.doi.org/10.5155/eurjchem.9.1.44-48.1679.

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Pyrano[3,2-c]quinolones are commonly found in alkaloids, manifesting diverse biological activities. In this work, 2-amino-6-methyl-5-oxo-4-substituted-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitriles and ethyl 2-amino-4-(substituted)-6-methyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylates have been synthesized efficiently from reaction of 4-hydroxy-1-methylquinolin-2(1H)-one, aldehydes and active methylene nitriles in one-pot three component reaction in aqueous medium, containing catalytic amount of ethanolamine resulting in 70-95% yields.

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9

Provatas, Anthony A., Gary A. Epling, and James D. Stuart. "Synthesis and Photocleavage of Quinoline Methyl Ethers: A Mild and Efficient Method for the Selective Protection and Deprotection of the Alcohol Functionality." Australian Journal of Chemistry 69, no. 7 (2016): 763. http://dx.doi.org/10.1071/ch15627.

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The synthesis and photocleavage of quinolinyl methyl ether-protected alcohols is reported in this study. A variety of quinoline methyl chlorides were synthesized, and protection of the various alcohols was performed via a substitution reaction in the presence of a strong base. Photocleavage of the quinolinyl methyl ether moiety proceeded under visible light with the formation of the charged quinolinyl radical intermediate through a single-electron transfer in the presence of a photosensitizer dye leading to the deprotected alcohol in excellent yields. The utility of triethylamine as a sacrific

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10

Munir, Rubina, Noman Javid, Muhammad Zia-ur-Rehman, et al. "Synthesis of Novel N-Acylhydrazones and Their C-N/N-N Bond Conformational Characterization by NMR Spectroscopy." Molecules 26, no. 16 (2021): 4908. http://dx.doi.org/10.3390/molecules26164908.

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In this article, a synthesis of N’-(benzylidene)-2-(6-methyl-1H-pyrazolo[3,4-b]quinolin-1-yl)acetohydrazides and their structural interpretation by NMR experiments is described in an attempt to explain the duplication of some peaks in their 1H- and 13C-NMR spectra. Twenty new 6-methyl-1H-pyrazolo[3,4-b]quinoline substituted N-acylhydrazones 6(a–t) were synthesized from 2-chloro-6-methylquinoline-3-carbaldehyde (1) in four steps. 2-Chloro-6-methylquinoline-3-carbaldehyde (1) afforded 6-methyl-1H-pyrazolo[3,4-b]quinoline (2), which upon N-alkylation yielded 2-(6-methyl-1H-pyrazolo[3,4-b]quinolin

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11

Abelt, Christopher, Ian Day, Junkai Zhao, and Robert Pike. "Fluorescence of Half-Twisted 10-Acyl-1-methyltetrahydrobenzoquinolines." Molecules 29, no. 13 (2024): 3016. http://dx.doi.org/10.3390/molecules29133016.

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The steric interference of proximal dialkyl amino and acyl groups at the peri (1,8) positions of naphthalene affects the intramolecular charge transfer fluorescence. Previous studies indicate that acyl and freely rotating dimethyl amino groups twist toward coplanarity with the naphthalene ring in the excited state. The present study examines the effect of constraining the amino group in a ring. The photophysical properties of 2,2-dimethyl-1-(1-methyl-1,2,3,4-tetrahydrobenzo[h]quinolin-10-yl)propan-1-one (4), ethyl 1-methyl-1,2,3,4-tetrahydrobenzo[h]quinoline-10-carboxylate (5), and 1-methyl-1,

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12

Almansour, Abdulrahman I., Natarajan Arumugam, Saradh Prasad, et al. "Investigation of the Optical Properties of a Novel Class of Quinoline Derivatives and Their Random Laser Properties Using ZnO Nanoparticles." Molecules 27, no. 1 (2021): 145. http://dx.doi.org/10.3390/molecules27010145.

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Quinoline Schiff bases display potential applications in optoelectronics and laser fields because of their unique optical properties that arise from extensive delocalization of the electron cloud, and a high order of non-linearity. In this context, a new class of conjugated quinoline-derivative viz. N-(quinolin-3-ylmethylene)anilines were synthesized from 2-hydroxyquinoline-3-carbaldehyde in two good yielding steps. The ability of these imines to accept an electron from a donor is denoted by their electron acceptor number and sites, which is calculated using density functional theory (DFT). Th

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13

Frites, Wahiba, Massaab Khalfaoui, Lamouri Hammal, Vera L. M. Silva та Artur M. S. Silva. "Ultrasound-Assisted Wittig Reaction for the Synthesis of 3-Substituted 4-Chloroquinolines and Quinolin-4(1H)-ones with Extended π-Conjugated Systems". Journal of Chemistry 2022 (5 грудня 2022): 1–12. http://dx.doi.org/10.1155/2022/4807767.

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3-(Vinyl-/buta-1,3-dien-1-yl/4-phenylbuta-1,3-dien-1-yl)-4-chloro quinolines and quinolin-4(1H)-ones were synthesized by ultrasound-assisted Wittig reaction of the corresponding 4-chloro-3-formylquinoline and 3-formylquinolin-4(1H)-ones with nonstabilized ylides. Ease execution, mild conditions, and high yields make this method exploitable for the generation of libraries of 3-substituted 4-chloroquinolines and quinolin-4(1H)-ones with extended π-conjugated systems. To demonstrate the usefulness of these compounds as precursors for the synthesis of more complex structures, 3-vinylquinolin-4(1H)

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14

Boyd, Derek R., Narain D. Sharma, Ludmila V. Modyanova, et al. "Dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems." Canadian Journal of Chemistry 80, no. 6 (2002): 589–600. http://dx.doi.org/10.1139/v02-062.

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Toluene dioxygenase-catalyzed dihydroxylation, in the carbocyclic rings of quinoline, 2-chloroquinoline, 2-methoxyquinoline, and 3-bromoquinoline, was found to yield the corresponding enantiopure cis-5,6- and -7,8-dihy dro diol metabolites using whole cells of Pseudomonas putida UV4. cis-Dihydroxylation at the 3,4-bond of 2-chloroquino line, 2-methoxyquinoline, and 2-quinolone was also found to yield the heterocyclic cis-dihydrodiol metabolite, (+)-cis-(3S,4S)-3,4-dihydroxy-3,4-dihydro-2-quinolone. Heterocyclic cis-dihydrodiol metabolites, resulting from dihydroxylation at the 5,6- and 3,4-bon

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15

Sabo, T., D. Kut, M. Kut, M. Onysko, and V. Lendel. "TELLURO-INDUCED CYCLISATION 2-(BUT-2-ENYLTHIO)QUINOLINECARBALDEHYDE AND QUINOLINE-4-ONE." Scientific Bulletin of the Uzhhorod University. Series «Chemistry» 48, no. 2 (2023): 73–78. http://dx.doi.org/10.24144/2414-0260.2022.2.73-78.

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Aryltellurium trichlorides have proven themselves as good cyclizing reagents in electrophilic intramolecular cyclization reactions, mainly of propenyl derivatives of heterocycles. On the other hand, information on the use of butenyl derivatives in reactions with p-alkoxyphenyltellurtrichlorides is limited. In this work, the regioselectivity of the process of electrophilic intramolecular cyclization of but-2-enyl thioethers of quinoline-3carbaldehyde and quinazolin-4-one with p-methoxyphenyltellurium trichloride was investigated. It was established that, as a result of the tellurium-induc

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16

Jiang, Shujiao, Sijia Ding, Yasong Zhou, Shenghua Yuan, Xinguo Geng, and Zhengkai Cao. "Substituent Effects of the Nitrogen Heterocycle on Indole and Quinoline HDN Performance: A Combination of Experiments and Theoretical Study." International Journal of Molecular Sciences 24, no. 3 (2023): 3044. http://dx.doi.org/10.3390/ijms24033044.

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Hydrodenitrogenation (HDN) experiments and density functional theory (DFT) calculations were combined herein to study the substituent effects of the nitrogen heterocycle on the HDN behaviors of indole and quinoline. Indole (IND), 2-methyl-indole (2-M-IND), 3-methyl-indole (3-M-IND), quinoline (QL), 2-methyl-quinoline (2-M-QL) and 3-methyl-quinoline (3-M-QL) were used as the HDN reactant on the NiMo/γ-Al2O3 catalyst. Some key elementary reactions in the HDN process of these nitrogen compounds on the Ni-Mo-S active nanocluster were calculated. The notable difference between IND and QL in the HDN

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17

Li, Yang, Ming-qin Chang, Feng Gao, and Wen-tao Gao. "Facile synthesis of fused quinolines via intramolecular Friedel–Crafts acylation." Journal of Chemical Research 2008, no. 11 (2008): 640–41. http://dx.doi.org/10.3184/030823408x375070.

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The intramolecular cyclisation of 6-[(phenoxy/phenylthio)methyl][1,3]dioxolo[4,5-g]quinoline-7-carboxylic acids to [1]benzoxepino[3,4-b][1,3]dioxolo[4,5-g]quinolin-12(6H)-onesand[1]benzothiepino[3,4-b][1,3]dioxolo[4,5-g]quinolin-12(6H)-ones in the presence of Eaton's reagent (P2O5-MeSO3H) is described. This cyclisation protocol requires milder conditions than those traditionally employed and is characterised by relatively low reaction temperatures and ease of product isolation.

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18

Rádl, Stanislav, and Viktor Zikán. "Synthesis of 1,2, and 9-methyl derivatives of 4,9-dihydro-6-methoxy-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline and 4,9-dihydro-6-hydroxy-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline and their antiviral activity." Collection of Czechoslovak Chemical Communications 52, no. 3 (1987): 788–92. http://dx.doi.org/10.1135/cccc19870788.

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The paper describes syntheses of 4,9-dihydro-6-methoxy-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline (Ia), its 1-methyl derivative (Ic), 1,9-dimethyl derivative (Ie), 2-methyl derivative (IIa), and 2,9-dimethyl derivative (IIc). Demethylation of these compounds with hydrobromic acid afforded 4,9-dihydro-6-hydroxy-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline (Ib), its 1-methyl derivative (Id), 1,9-dimethyl derivative (If), 2-methyl derivative (IIb), and 2,9-dimethyl derivative (IId) respectively. 4,9-Dihydro-6-hydroxy-3,9-dimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (Ig) was prepared by demeth

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19

Sabo, T., D. Kut, M. Kut, M. Onysko, and V. Lendel. "TELLURO-INDUCED CYCLIZATION OF 2-ALLYLTHIOQUINOLINECARBALDEHYDE." Scientific Bulletin of the Uzhhorod University. Series «Chemistry» 46, no. 2 (2022): 74–79. http://dx.doi.org/10.24144/2414-0260.2021.2.74-79.

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It is known that thiazolopyrimidines with an exocyclic aryl tellurium moiety exhibit antimalarial activity against the deadliest strain of Plasmodium falciparum. For expanding the number of potentially biologically active compounds with an exocyclic aryl tellurium moiety, a study of tellurium-induced heterocyclization of 2-allylthioquinoline-3-carbaldehyde with p-methoxyphenylteltur trichloride was performed. The selection of this synton is motivated by the fact that quinoline derivatives are used as drugs in the treatment of malaria. The starting compound 2-allylthioquinoline-3-carbalde

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20

Patel, Darshana D., and Vikram N. Panchal. "Studies on Metal Complexes of Pyrazole Bearing Ligand with Their Antimicrobial Screening." Oriental Journal Of Chemistry 40, no. 5 (2024): 1394–98. http://dx.doi.org/10.13005/ojc/400522.

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In present research article, we reported the synthesise of novel hetertocyclic ligand namely,5-((3-((1H-benzimidazol-1-yl)methyl)-5-phenyl-1H-pyrazol-1-yl) methyl)-8-hydroxy quinoline (BIPPHQ) from 5-chloro methyl-8-hydroxy quinoline and 1-((5-phenyl-1H-pyrazol-3-yl) methyl)-1H-benzimidazole (BIPP). The BIPP was synthsised by the reaction between hydrazine hydrate with 1-(1H-benzimidazol-1-yl)-4-phenylbut-3-en-2-one (BIPB), which was synthesisd from 1-(1H-benzimidazol-1-yl)propan-2-one (BIP) and benzaldehyde. The transition metal complxes of 5-((3-((1H-benzimidazol-1-yl)methyl)-5-phenyl-1H-pyr

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21

Zhang, Rui Fang, Rui Rui Zhang, Yu Jing Lu, et al. "5-Methyl-Benzofuro[3,2-b]quinoline Derivatives as DNA Binders." Advanced Materials Research 711 (June 2013): 73–78. http://dx.doi.org/10.4028/www.scientific.net/amr.711.73.

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Several derivatives of 5-methyl-benzofuro [3,2-quinoline (O-isostere of cryptolepine) were synthesized. Spectrometric experiments and molecular modeling indicated that these derivatives interacted with duplex DNA by intercalation binding mode. The derivatives with aniline substituent exhibited superior DNA binding affinity to that of lead compound 5-methyl-benzofuro [3,2-quinoline.

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22

Kwak, Sang Woo, Ju Hyun Hong, Sang Hoon Lee, et al. "Synthesis and Photophysical Properties of a Series of Dimeric Indium Quinolinates." Molecules 26, no. 1 (2020): 34. http://dx.doi.org/10.3390/molecules26010034.

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A novel class of quinolinol-based dimeric indium complexes (1–6) was synthesized and characterized using 1H and 13C(1H) NMR spectroscopy and elemental analysis. Compounds 1–6 exhibited typical low-energy absorption bands assignable to quinolinol-centered π–π* charge transfer (CT) transition. The emission spectra of 1–6 exhibited slight bathochromic shifts with increasing solvent polarity (p-xylene < tetrahydrofuran (THF) < dichloromethane (DCM)). The emission bands also showed a gradual redshift, with an increase in the electron-donating effect of substituents at the C5 position of the q

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23

Hafiz, Ibrahim Saad Abdel, Elham Sayed Darwish, and Fivian Farouk Mahmoud. "Utility of 3-Aminocrotononitrile in the Synthesis of New Methyl 1,4-Dihydropyridine, Methylquinoline and Thiophene Derivatives: Reactivity of the Methyl Function in Alkyl 1,4-Dihydropyridine and Methyl Quinoline Derivatives towards Some Electrophilic Reagents." Journal of Chemical Research 23, no. 9 (1999): 536–37. http://dx.doi.org/10.1177/174751989902300909.

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Ivanova, Maria, Joana Zaharieva, Martin Tsvetkov, Vesela Lozanova, Bernd Morgenstern, and Rumen Lyapchev. "8-(2-Methoxyphenyl)-6-methyl-2-(1-methyl-1H-benzo[d]imidazol-2-yl)quinoline." Molbank 2024, no. 3 (2024): M1874. http://dx.doi.org/10.3390/m1874.

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For very first time, we report the synthesis of 8-(2-methoxyphenyl)-6-methyl-2-(1-methyl-1H-benzo[d]imidazol-2-yl)quinoline 1. This was achieved in several steps, including usage of the Suzuki reaction for functionalization of 2-(1H-benzo[d]imidazol-2-yl)quinoline moiety. The new compound exhibits blue fluorescence. Its structure was confirmed with 1D and 2D NMR spectroscopy, IR spectroscopy, high-resolution mass spectrometry and X-ray analysis.

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Wantulok, Jakub, Marcin Szala, Andrea Quinto, et al. "Synthesis, Electrochemical and Spectroscopic Characterization of Selected Quinolinecarbaldehydes and Their Schiff Base Derivatives." Molecules 25, no. 9 (2020): 2053. http://dx.doi.org/10.3390/molecules25092053.

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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. Addit

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Kovalenko, Sergiy M., Oleksandr G. Drushlyak, Svitlana V. Shishkina, et al. "Methylation of Methyl 4-Hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate: Synthetic, Crystallographic, and Molecular Docking Studies." Molecules 25, no. 18 (2020): 4238. http://dx.doi.org/10.3390/molecules25184238.

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Consecutive alkylation of 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate by CH3I has been investigated to establish regioselectivity of the reaction for reliable design and synthesis of combinatorial libraries. In the first stage, the product of S-methylation-methyl 4-hydroxy-2-(methylthio)quinoline-3-carboxylate was obtained. The subsequent alkylation with CH3I led to the formation of both O- and N-methylation products mixture-methyl 4-methoxy-2-(methylthio)quinoline-3-carboxylate and methyl 1-methyl-2-(methylthio)-4-oxo-1,4-dihydroquinoline-3-carboxylate with a predominance of O-methy

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Ghosh, Bidhan, Satabdi Bera, Pintu Ghosh, and Rajarshi Samanta. "Rh(iii)-Catalyzed mild straightforward synthesis of quinoline-braced cyclophane macrocycles via migratory insertion." Chemical Communications 57, no. 97 (2021): 13134–37. http://dx.doi.org/10.1039/d1cc04418d.

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A mild and straightforward Rh(iii)-catalysed macrocylization strategy is developed to deliver quinoline braced cyclophane type macrocycles based on migratory insertion of metal–carbenes into the C8-methyl group of quinoline scaffolds.

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Zacharopoulos, Nikolaos, Gregor Schnakenburg, Eleni I. Panagopoulou, Nikolaos S. Thomaidis, and Athanassios I. Philippopoulos. "Pyridine–Quinoline and Biquinoline-Based Ruthenium p-Cymene Complexes as Efficient Catalysts for Transfer Hydrogenation Studies: Synthesis and Structural Characterization." Molecules 30, no. 14 (2025): 2945. https://doi.org/10.3390/molecules30142945.

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Searching for new and efficient transfer hydrogenation catalysts, a series of new organometallic ruthenium(II)-arene complexes of the formulae [Ru(η6-p-cymene)(L)Cl][PF6] (1–8) and [Ru(η6-p-cymene)(L)Cl][Ru(η6-p-cymene)Cl3] (9–11) were synthesized and fully characterized. These were prepared from the reaction of pyridine–quinoline and biquinoline-based ligands (L) with [Ru(η6-p-cymene)(μ-Cl)Cl]2, in 1:2 and 1:1, metal (M) to ligand (L) molar ratios. Characterization includes a combination of spectroscopic methods (FT-IR, UV-Vis, multi nuclear NMR), elemental analysis and single-crystal X-ray c

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Levendis, Demetrius C., Jeffrey Moffit, Benjamin Staskun, and Theodorus van Es. "Thionyl Chloride-induced Conversion of 1-Ethyl-1,4-dihydro-2-methyl-4-oxoquinoline-3-carboxylic Acids to Highly Functionalised Thieno[3,4-b]quinoline Derivatives." Journal of Chemical Research 23, no. 10 (1999): 614–15. http://dx.doi.org/10.1177/174751989902301014.

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Warming a title acid with SOCl2 gives the corresponding 3,3,9-trichlorothieno[3,4- b]quinolin-1 (3 H)-one whereas reaction at room temperature leads to the intermediate 3,3-dichloro-4-ethylthieno[3,4- b]quinoline-1(3 H),9(4 H)-dione product as established from the respective X-ray crystallographic determinations.

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30

Erazua, E. A., and B. B. Adeleke. "A Computational Study of Quinoline Derivatives as Corrosion Inhibitors for Mild Steel in Acidic Medium." Journal of Applied Sciences and Environmental Management 23, no. 10 (2019): 1819–24. http://dx.doi.org/10.4314/jasem.v23i10.8.

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The corrosion inhibition efficiency of three quinoline derivatives namely; ethyl 2-(((8-hydroxyquinolin5-yl)methyl)amino)acetate (QN1), 5-((benzylamino)methyl)quinolin-8-ol (QN2) and 5-(azidomethyl)quinolin-8-ol (QN3) on the mild steel in 1 M HCl was studied using density functional theory (DFT) calculations and quantitative structural activity relationship (QSAR) approach. The experimental inhibition efficiency were discussed in relation with molecular descriptors such as such as EHOMO (energy of the highest occupied molecular orbital), ELUMO (energy of the lowest unoccupied molecular orbital

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31

Anjana, S. S., Babu Varghese, and Edamana Prasad. "Dinuclear cobalt(II) complexes with double phosphate ester bridges and tetradentate ligands having anisole or quinoline appendages." Acta Crystallographica Section C Structural Chemistry 73, no. 6 (2017): 492–97. http://dx.doi.org/10.1107/s2053229617007355.

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Phosphate esters provide a rigid and stable polymeric backbone in nucleic acids. Metal complexes with phosphate ester groups have been synthesized as structural and spectroscopic models of phosphate-containing enzymes. Dinucleating ligands are used extensively to synthesize model complexes since they provide the support required to stabilize such complexes. The crystal structures of two dinuclear CoII complexes, namely bis(μ-diphenyl phosphato-κ2 O:O′)bis({2-methoxy-N,N-bis[(pyridin-2-yl)methyl]aniline-κ4 N,N′,N′′,O}cobalt(II)) bis(perchlorate), [Co(C12H10O4P)2(C19H19N3O)2](ClO4)2, and bis(μ-d

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32

Rádl, Stanislav, Viktor Zikán, and František Šmejkal. "Syntheses of some N-carboxymethyl derivatives of 4,9-dihydro-3-methyl-4-oxo-1H-(2H)-pyrazolo[3,4-b]quinoline with antiviral effects." Collection of Czechoslovak Chemical Communications 50, no. 9 (1985): 2010–14. http://dx.doi.org/10.1135/cccc19852010.

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The paper describes the syntheses of 4,9-dihydro-9-carboxymethyl-1,3-dimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (Ic), 4,9-dihydro-9-carboxymethyl-2,3-dimethyl-4-oxo-2H-pyrazolo[3,4-b]quinoline (IIc), 4,9-dihydro-1-carboxymethyl-3-methyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (Id), 4,9-dihydro-1-carboxymethyl-3,9-dimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (If) and 4,9-dihydro-2-carboxymethyl-3,9-dimethyl-4-oxo-2H-pyrazolo[3,4-b]quinoline (IIf). The compounds were tested in vivo in mice for their efficacy against the virus A2-Hongkong and the encephalomyocarditis virus.

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33

lenin, Santhadani, Ramasamy sujatha, and Shanmugasundaram Palanisamy. "Pharmacological Properties And Bioavailability Studies Of 3-Methyl Quinoline." International Journal of Pharma and Bio Sciences 12, no. 1 (2022): 100–104. http://dx.doi.org/10.22376/ijpbs/lpr.2022.12.1.l100-104.

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Amongst heterocyclic compounds, quinoline is the privileged scaffold that appears as a significant assembly motif for the development of new drug entities. Quinoline and its derivatives tested with diverse biological activity constitute an important class of compounds for new drug development. Therefore, many scientific communities have developed these compounds as intent structures and evaluated their biological activities. Our goal is to discover bioavailability, relative bioavailability, definition and assembly factors that may influence the bioavailability of a medication item, physiologic

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34

Hazra, Ananta, Ankita Roy, Abhishek Mukherjee, Guru Prasad Maiti, and Partha Roy. "Remarkable difference in Al3+ and Zn2+ sensing properties of quinoline based isomers." Dalton Transactions 47, no. 39 (2018): 13972–89. http://dx.doi.org/10.1039/c8dt02856g.

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4-Methyl-2-((quinolin-6-ylimino)methyl)phenol and 4-methyl-2-((quinolin-2-ylimino)methyl)phenol have been found to be dual fluorescence chemosensors for Al<sup>3+</sup> and Zn<sup>2+</sup> ions, but their sensing ability varies.

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35

Deady, Leslie W., and Clare L. Smith. "Tetracycle Formation from the Reaction of Acetophenones with 1-Aminoanthraquinone, and Further Annulation of Pyridine and Diazepine Rings." Australian Journal of Chemistry 56, no. 12 (2003): 1219. http://dx.doi.org/10.1071/ch03136.

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Acetophenones (H, o-, m-, p-Cl, o-aza) react with aminoanthraquinone in pyridine containing solid sodium hydroxide to form 6-(arylcarbonyl)methyl-2-aryl-7H-naphtho[1,2,3-de]quinolin-7-ones (with the 4-(arylcarbonyl)methyl isomer as minor product). Preformed 7H-benzo[e]perimidin-7-one with acetophenone underwent the second part of this process, i.e. nucleophilic substitution to form 6-phenacyl-7H-benzo-[e]perimidin-7-one. Further reactions are described, including cyclization with ammonium acetate/acetic acid to 2,7-diphenyl-1,6-diazabenzo[e]pyrene and 7-phenyl-1,3,8-triazabenzo[e]pyrene, respe

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36

Ladani, Gaurav G., and Manish P. Patel. "Regioselective one-pot three-component synthesis of quinoline based 1,2,4-triazolo[1,5-a]quinoline derivatives." RSC Advances 5, no. 94 (2015): 76943–48. http://dx.doi.org/10.1039/c5ra15560f.

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A one-pot three-component approach for the synthesis of 2-(piperidin-1-yl) quinoline based 1,2,4-triazolo[1,5-a]quinoline derivatives (4a–l) has been described by the reaction of aldehyde (1a–f), methyl 2-cyanoacetate (2) and enaminones (3a–b).

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37

N., D. SHARMA, KUMAR SANTOSH, V. BAKORE P., and C. JOSHI B. "Condensation of 2-Anilino-4-methylquinoline Derivatives with Substituted-diethylmalonate and Studies of Isomerism through Nmr Spectra." Journal of Indian Chemical Society Vol. 64, Aug 1987 (1987): 481–82. https://doi.org/10.5281/zenodo.6199354.

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Department of Chemistry, University of Rajasthan, Jaipur-302 004 <em>Manuscript received 6 February 1979, accepted 22 January 1987</em> 2 [<em>N</em>-(2,2-Dicarbethoxyvinyl)anilino]-4-methyl-quinoline (6), 2-[<em>N</em>-(2,2-dicarbethoxyvinyl)-2-chloroanilino]-4-methylquinoline (7) and 2-N-(2,2-dicarbethoxyvinyl)-4- methylquinoline (8) were prepared by condensing ethoxymethylene diethyl malonate (4) with 2-anilino-4-methyl-quinoline (1), 2-(2-chlorosailino)-4-methylquinoline (2) and 2.(4-methoxyanilino)-4-methyl quinoline (3), respectively. 2-[<em>N</em>-(2-Carbethoxy-2- pbenacetyl)anilin

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38

Torres Suarez, Elaine, Diana Susana Granados-Falla, Sara María Robledo, Javier Murillo, Yulieth Upegui, and Gabriela Delgado. "Antileishmanial activity of synthetic analogs of the naturally occurring quinolone alkaloid N-methyl-8-methoxyflindersin." PLOS ONE 15, no. 12 (2020): e0243392. http://dx.doi.org/10.1371/journal.pone.0243392.

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Leishmaniasis is a neglected, parasitic tropical disease caused by an intracellular protozoan from the genus Leishmania. Quinoline alkaloids, secondary metabolites found in plants from the Rutaceae family, have antiparasitic activity against Leishmania sp. N-methyl-8-methoxyflindersin (1), isolated from the leaves of Raputia heptaphylla and also known as 7-methoxy-2,2-dimethyl-2H,5H,6H-pyran[3,2-c]quinolin-5-one, shows antiparasitic activity against Leishmania promastigotes and amastigotes. This study used in silico tools to identify synthetic quinoline alkaloids having structure similar to th

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39

Kafka, Stanislav, Andrej Pevec, Karel Proisl, Roman Kimmel, and Janez Košmrlj. "4-Hydroxy-1-methyl-3-phenylquinolin-2(1H)-one." Acta Crystallographica Section E Structure Reports Online 69, no. 2 (2013): o231. http://dx.doi.org/10.1107/s1600536813000226.

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In the title compound, C16H13NO2, the quinoline system is approximately planar with a maximum deviation from the least-squares plane of 0.059 (1) Å for the N atom. The phenyl ring is rotated by 62.16 (4)° with respect to the plane of the quinoline system. In the crystal, O—H...O hydrogen bonds link molecules into infinite chains running along theb-axis direction.

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40

Ma, Yan Li, Gui Zhen Fang, Ying Mei Ma, Rui Zhang, and Zhong Ling Jin. "Enhanced Photocatalytic Activity for Titanium Dioxide in Sunlight by a Kind of Squarylium Cyanine Dye." Advanced Materials Research 113-116 (June 2010): 1672–74. http://dx.doi.org/10.4028/www.scientific.net/amr.113-116.1672.

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The research synthesized bis-(2-methyl quinoline) squarylium cyanine (abbr. QYCD). It was used as dye to enhance the photocatalytic activity of nano-TiO2 in sunlight. Then the photocatalytic process of removal of benzene was investigated indoor air. Results reveal that bis-(2-methyl quinoline)- squarylium cyanine has an intense absorption in the light region of 200nm - 800 nm. The Benzene removal of QYCD-nano-TiO2 complex catalyst at 78h was 97.69%, at the same time it was 36.96% higher as compared with that of nano-TiO2.

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41

Shiri, Morteza, Maryam-Sadat Tonekaboni, Zahra Tanbakouchian, and Soma Majedi. "Synthesis of [1,4]Oxathiepino[5,6-b]quinolines via Base-Mediated Intramolecular Hydroalkoxylation." SynOpen 06, no. 01 (2022): 7–10. http://dx.doi.org/10.1055/s-0040-1719868.

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AbstractA base-mediated intramolecular hydroalkoxylation that was used to prepare a series of seven-membered S,O-heterocycles is described. 2-Thiopropargyl-3-hydroxymethyl quinolines were prepared starting from 2-mercaptoquinoline-3-carbaldehydes, via S-propargylation and reduction of a formyl group. Interestingly, 2-mercaptopropargyl-3-hydroxymethyl quinolines were converted into the corresponding oxathiepinoquinolines in the presence of t-BuOK. It is proposed that the S-propargyl moiety, in the presence of base, is converted into its allenyl isomer; subsequent addition of a hydroxyl group to

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42

Derabli, Chamseddine, Raouf Boulcina, Sofiane Bouacida, Hocine Merazig, and Abdelmadjid Debache. "2-(2-Chloro-8-methylquinolin-3-yl)-4-phenyl-1,2-dihydroquinazoline." Acta Crystallographica Section E Structure Reports Online 69, no. 11 (2013): o1719—o1720. http://dx.doi.org/10.1107/s1600536813029334.

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In the title compound, C24H18ClN3, the dihydroquinazoline and methyl-substituted quinoline benzene rings make a dihedral angle of 78.18 (4)° and form dihedral angles of 45.91 (5) and 79.80 (4)°, respectively, with the phenyl ring. The dihedral angle between the phenyl ring of dihydroquinazoline and the methyl-substituted benzene ring of quinoline is 78.18 (4)°. The crystal packing can be described as crossed layers parallel to the (011) and (0-11) planes. The structure features N—H...N hydrogen bonds and π–π interactions [centroid–centroid distance between phenyl rings = 3.7301 (9) Å].

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43

Lukevics, Edmunds, Edgars Abele, Pavel Arsenyan, et al. "Synthesis and Cytotoxicity of Silicon Containing Pyridine and Quinoline Sulfides." Metal-Based Drugs 9, no. 1-2 (2002): 45–51. http://dx.doi.org/10.1155/mbd.2002.45.

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Silicon containing pyridine and quinoline sulfides have been prepared using phase transfer catalytic system thiol/alkyl halide / solid KOH/18-crown-6 / toluene. The target S-ethers were isolated in yields up to 81%. The cytotoxicity of the synthesized compounds was studied. Among pyridine sulfides S-[3-(1-methyl- 1-silacyclohexyl)propyl] derivatives 5e and 6e exhibit the highest cytotoxicity. Aliphatic silicon derivatives were considerably less active. 8-[(Trimethylsilylmethyl)thio]quinoline (8a) exhibits the highest activity among quinoline sulfides.

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44

Faizi, Md Serajul Haque, та Pratik Sen. "[Bis(quinolin-2-ylcarbonyl)amido-κ3N,N′,N′′]bromido(N,N-dimethylformamide-κO)copper(II)". Acta Crystallographica Section E Structure Reports Online 70, № 6 (2014): m206—m207. http://dx.doi.org/10.1107/s1600536814010058.

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In the mononuclear title complex, [CuBr(C20H12N3O2)(C3H7NO)], synthesized from the quinoline-derived reduced Schiff base 4-(quinolin-2-ylmethyl)aminophenol, the coordination geometry around Cu2+is distorted square-pyramidal, comprising a bromide anion at the apex [Cu—Br = 2.4671 (5) Å]. The base of the pyramid is built up from one dimethylformamide O-atom donor [Cu—O = 2.078 (2) Å] and three N-atom donors from the monoanionic, tridentate bis(quinolin-2-ylcarbonyl)diimide ligand [Cu—Ndiimide= 1.941 (3) Å, and Cu—Nquinolyl= 2.060 (3) and 2.049 (3) Å]. An intramolecular C—H...O occurs. In the cry

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45

Weng, Wei-Zhao, Jiang-Shan Guo, Kai-Xuan Liu, et al. "Metal-free oxidative C(sp3)–H functionalization: a facile route to quinoline formaldehydes from methyl-azaheteroarenes." Canadian Journal of Chemistry 98, no. 4 (2020): 179–83. http://dx.doi.org/10.1139/cjc-2019-0456.

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A facile protocol for the synthesis of quinoline formaldehydes via direct oxidative C–H bonds functionalization of methyl-azaheteroarenes in the presence of I2–DMSO has been described. This method is metal-free and easy to operate. This reaction provided a convenient route for the preparation of a range of important quinoline formaldehydes.

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46

Sharma, Naveen. "Design, Synthesis, And Biological Activity Of Some Novel Quinoline Derivatives." Journal of Neonatal Surgery 14, no. 7 (2025): 662–69. https://doi.org/10.5281/zenodo.15482274.

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Here, some novel quinoline derivatives are presented in an effort to synthesise some molecules with strong antioxidantactivity. First, 7-methyl or 8-methyl substituted 2-cholro-3-formylquinolines (Ia, b) were made utilising the Vilsemeir-Hackreagent method. Additional substitutions of 7-methyl or 8-methyl Compound (I) reacted with 4M HCl upon microwaveirradiation to produce 2-hydroxy quinoline-3-carbaldehyde (IIa, b). Subsequent treatment with various substituted hydrazidesproduced the new Schiff bases of quinoline III (a-f). TLC and melting point were used to assess the synthesised compounds'

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47

Bazgir, Ayoob. "Ethyl 2-methyl-4-phenylquinoline-3-carboxylate." Acta Crystallographica Section E Structure Reports Online 65, no. 6 (2009): o1382. http://dx.doi.org/10.1107/s1600536809018625.

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In the molecule of the title compound, C19H17NO2, the quinoline ring system is planar [maximum deviation 0.021 (3) Å] and oriented with respect to the phenyl ring at a dihedral angle of 80.44 (4)°. Intramolecular C—H...O interactions result in the formation of five- and six-membered rings having planar and envelope conformations, respectively. In the crystal structure, intermolecular C—H...O interactions link the molecules into centrosymmetric dimers formingR22(12) ring motifs. π–π contacts between the rings of the quinoline system [centroid-to-centroid distance = 3.812 (1) Å] may further stab

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48

Gharib, Ali, Bibi Robabeh Hashemipour Khorasani, Manouchehr Jahangir, Mina Roshani, and Reza Safaee. "Catalytic Synthesis of 3-Methyl-1-phenyl-1H-benzo[g]pyrazolo[3,4-b]quinoline-5,10-dione Derivatives Using Cerium Oxide Nanoparticles as Heterogeneous Catalyst in Green Conditions." Organic Chemistry International 2013 (August 6, 2013): 1–5. http://dx.doi.org/10.1155/2013/584708.

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We have developed a new methodology for the synthesis of 3-methyl-1-phenyl-1H-benzo[g]pyrazolo[3,4-b]quinoline-5,10-dione derivatives in excellent yields. A new green chemistry protocol with the reusability of the nanoparticle as catalyst has been developed for the synthesis of 3-methyl-1-phenyl-1H-benzo[g]pyrazolo[3,4-b]quinoline-5,10-dione derivatives via one-pot reaction of 3-methyl-1-phenyl-1H-pyrazol-5-amine, arylaldehydes, and 2-hydroxynaphthalene-1,4-dione in water as green solvent and using cerium oxide nanoparticles (CONPs) as heterogeneous catalyst. The present methodology affords se

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49

Medvedeva, Svetlana M., Alexey V. Movchan, Ksenia A. Bondarenko, Ksenia Dz Shikhalieva, and Khidmet S. Shikhaliev. "Preparation of individual derivatives in 1,3-oxazino[5,4,3-ij]quinolines and 1,4-oxazino[2,3,4-ij]quinolines series by column chromatography and their mass spectrometric study." Сорбционные и хроматографические процессы 23, no. 4 (2023): 705–15. http://dx.doi.org/10.17308/sorpchrom.2023.23/11577.

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Hundreds of highly effective compounds that have a complex of practically useful properties are known among tricyclic hydroquinolines. Therefore, the production of new compounds of high purity in this series and identification of the features of their behaviour under the influence of electron impact for the determination of their structures is important. Previously, we synthesized 1,3-oxazino[5,4,3-ij]quinoline-1,3-diones and 1,4-oxazino[2,3,4-ij]quinoline-2,3-diones, but the nature of the mass spectral decay for the determination of their structures was not discussed. In this study, using thi

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50

Muchowski, Joseph M., and Michael L. Maddox. "Concerning the mechanism of the Friedländer quinoline synthesis." Canadian Journal of Chemistry 82, no. 3 (2004): 461–78. http://dx.doi.org/10.1139/v03-211.

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Detailed experiments regarding the mechanism of the Friedländer synthesis of quinolines from o-aminobenzaldehydes and simple aldehydes or ketones are described. Under the basic or acidic conditions commonly used in this reaction, it is concluded that the first step involves a slow intermolecular aldol condensation of the aldehyde or ketone with the o-aminobenzaldehyde. The aldol adduct 5 generated in this manner then undergoes very rapid cyclization to 4, which subsequently loses water to produce the quinoline derivative 8. Both 5 and 4 are too short lived to be detectable (TLC), even when del

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