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Journal articles on the topic '4-oxo-quinoline'

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Published: 10 September 2021

Last updated: 29 July 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

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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3

Rádl, Stanislav, and Viktor Zikán. "Synthesis and biological activity of some basic-substituted 4,9-dihydro-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinolines." Collection of Czechoslovak Chemical Communications 53, no. 8 (1988): 1812–19. http://dx.doi.org/10.1135/cccc19881812.

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Compounds Ia, Ib were obtained by an alkylation of 4,9-dihydro-6-hydroxy-1,3,9-trimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (VIIb) with the respective dialkylaminoalkyl chloride. The same alkylation of 4,9-dihydro-6-hydroxy-2,3,9-trimethyl-4-oxo-2H-pyrazolo[3,4-b]quinoline (VIIIb) yielded compounds IIa and IIb. Similar alkylation of 4,9-dihydro-6-hydroxy-3,9-dimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (IXa) and its 6-methoxy derivative (IXb) afforded IIIa-IIId. Compound IV was prepared from 4-chloro-3-methyl-1H-pyrazolo[3,4-b]quinoline (Xa) via its 1-(3-dimethylaminopropyl)derivative (Xb). Compo

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4

Heleyová, Katarína, Dušan Ilavský, Vladimír Bobošík, and Naďa Prónayová. "Gould-Jacobs Reaction of 5- and 6-Amino-2-substituted Benzoxazoles. II. Reaction with 3-Ethoxymethylene-2,4-pentanedione and Ethyl 2-Ethoxymethylene-3-oxobutanoate." Collection of Czechoslovak Chemical Communications 61, no. 3 (1996): 371–80. http://dx.doi.org/10.1135/cccc19960371.

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Nucleophilic reaction of 5-amino- and 6-amino-2-substituted benzoxazoles 1 and 2 with 3-ethoxymethylene-2,4-pentanedione (3) gave compounds 5 and 6. Compounds 1 and 2 reacted with ethyl ethoxymethylene-3-oxobutanoate (4) under formation of compounds 7and 8. The substitution products 7 and 8 underwent thermal cyclization at high temperature (boiling mixture of diphenyl ether and biphenyl) to give angularly and linearly annelated derivatives of 5-acetyl-4-oxo-oxazolo[4,5-f]quinoline 9 and 7-acetyl-8-oxo-oxazolo[5,4-g]quinoline 10 (from 7), and derivatives of 8-acetyl-9-oxo-oxazolo[5,4-f]quinolin

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5

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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6

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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7

Rádl, Stanislav, and Viktor Zikán. "Syntheses of some 4-dialkylaminoalkylamino derivatives of 2,3-dimethyl-2H- and 3,9-dimethyl-9H-pyrazolo[3,4-b]quinoline." Collection of Czechoslovak Chemical Communications 51, no. 8 (1986): 1692–97. http://dx.doi.org/10.1135/cccc19861692.

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Reactions of 4-chloro-2,3-dimethyl-2H-pyrazolo[3,4-b]quinoline and 4-chloro-6-methoxy-2,3-dimethyl-2H-pyrazolo[3,4-b]quinoline with 3-dimethylaminopropylamine and/or 2-dimethylaminoethylamine afforded 4-(3-dimethylaminopropylamino)-2,3-dimethyl-2H-pyrazolo[3,4-b]quinoline (IIa), its 6-methoxy derivative (IIc), 4-(2-diethylaminoethylamino)-2,3-dimethyl-2H-pyrazolo[3,4-b]quinoline (IIb) and its 6-methoxy derivative (IId). Reaction of 4,9-dihydro-3,9-dimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline with thionyl chloride gave an intermediate, whose reaction with 3-dimethylaminopropylamine afforded 4-(3-

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8

V, Sangeetha. "SYNTHESIS OF ISOXAZOLO AND PYRAZOLINO ANNELATED CARBAZOLES FROM 2-(3'-(2'-CHLORO) QUINOLIDINE)-1-OXO-1, 2, 3, 4-TETRAHYDROCARBAZOLE AND 2-CHLORO-3-FORMYLQUINOLINE." Kongunadu Research Journal 2, no. 1 (2015): 29–31. http://dx.doi.org/10.26524/krj61.

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1-Oxo-1,2,3,4-tetrahydrocarbazole (1) on mixed aldol condensation with 2-chloro-3-formylquinoline (2) ielded 2-(3'-(2'-chloro)quinolidine)-1-oxo-1,2,3,4-tetrahydrocarbazole (3), which was further treated with hydroxylamine hydrochloride and hydrazine hydrate in separate reactions to afford 4,5-dihydro-3-3'-(2'-chloro) quinoline -isoxazolo [3,4-a]carbazole (4) and 3'-(2'-chloro)- quinoline- 3,3a,4,5- tetrahydro- 2Hpyrazolino [3,4-a]carbazole (5). The prepared compounds were elaluated for their invitro antibacterial and antifungal activities against certain pathogenic fungal and bacterial strain

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9

Yadav, Pradeep, and Y. C. Joshi. "Synthesis and Spectral Study of Novel Norfloxacin Derivatives." E-Journal of Chemistry 5, s2 (2008): 1154–58. http://dx.doi.org/10.1155/2008/357073.

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Reaction of [1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinolone-3-carboxylic acid (norfloxacin) with thiazole / benzothiazole diazonium chloride to get new piperazine substituted norfloxacin derivative. These norfloxacin derivatives were further condensed with variousβ-diketone to get novel acid derivatives of 1-Ethyl-6-fluoro-4-oxo-7- [4 (thiazol-2-yldiazenyl)-piperzin-1-yl]-1,4-dihydro-quinoline-3-carboxylic acid (6a-e) and 7-(4-(benzo[d]thiazol-2-yldiazenyl)piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1, 4-dihydroquinoline-3-carboxylic acid (6 f-j). Structures of these compounds were

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10

Zhang, Jinpeng, Jie Ding, Shu Yan, Liangce Rong, and Lichun Xu. "4-(4-Fluorophenyl)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile." Acta Crystallographica Section E Structure Reports Online 65, no. 6 (2009): o1354. http://dx.doi.org/10.1107/s1600536809017991.

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In the molecule of the title compound, C20H13FN2O, the fluorophenyl ring is oriented at a dihedral angle of 72.76 (3)° with respect to the fused benzene ring. In the crystal structure, intermolecular N—H...O, C—H...O and C—H...F interactions link the molecules into chains. π–π contacts between the quinoline and benzene rings [centroid–centroid distance = 3.918 (3) Å] may further stabilize the structure. A weak C—H...π interaction is also present. The O atom and two of the CH2groups of the quinoline ring system are disordered over two positions. The O atom was refined with occupancies of 0.489

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11

Akinboye, Emmanuel S., Ray J. Butcher, Sema Ozturk Yildirim, and John T. Isaacs. "4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-1,2-dihydroquinoline-3-carboxamide." Acta Crystallographica Section E Structure Reports Online 70, no. 3 (2014): o297—o298. http://dx.doi.org/10.1107/s1600536814003031.

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The title compound, C20H17F3N2O4, named tasquinimod, is a second-generation oral quinoline-3-carboxamide analogue, which is currently in phase III clinical trials for the treatment of metastatic prostate cancer. The quinoline unit is almost planar (r.m.s. deviation of fitted atoms = 0.0075 Å). The carboxamide side chain, substituted at position 3, is tilted by 88.07 (7)° to the quinoline plane. Both the methyl and carbonyl groups of this carboxamide side chain are in asynconformation. The 4-(trifluoromethyl)phenyl plane is inclined at 50.62 (17)° to the plane of the carboxamide side chain, and

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12

Yavari, Issa, Mahniya Hojati, Leila Azad, and Mohammad Halvagar. "A Synthesis of Spirocyclic Oxazinoisoquinolines and Oxazinoquinolines Bearing Thiazolopyrimidine Moieties." Synlett 29, no. 08 (2018): 1024–27. http://dx.doi.org/10.1055/s-0037-1609302.

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The reaction of isoquinoline or quinoline with dialkyl acetylenedicarboxylates in the presence of alkyl 2-{3,5-dioxo-5H-thiazolo[3,2-a]pyrimidin-2(3H)-ylidene}acetates (generated in situ from acetylenedicarboxylates and 2-thiouracils) led to dialkyl 2-(2-alkoxy-2-oxoethylidene)-5-oxo-2H,5H,11b′H-spiro{thiazolo[3,2-a]pyrimidine-3,2′-[1,3]oxazino[2,3-a]isoquinoline}-3′,4′-dicarboxylates or dialkyl 2-(2-alkoxy-2-oxoethylidene)-5-oxo-2H,4a′H,5H-spiro{thiazolo[3,2-a]pyrimidine-3,2′-[1,3]oxazino[3,2-a]quinoline}-1′,2′-dicarboxylates in good yields. The structure of the target compounds was confirmed

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13

Moussaoui, Oussama, El Mestafa El Hadrami, Ghita Benjalloune Touimi, et al. "Synthesis of a new serie of quinoline-carboxamides based on methylated aminoesters: NMR characterization and antimicrobial activity." Mediterranean Journal of Chemistry 9, no. 4 (2019): 326–36. http://dx.doi.org/10.13171/mjc941911231077sc.

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Ten new quinoline-carboxamides have been synthesized using the coupling reaction between 2-oxo-1,2-dihydroquinoline-4-carboxylic acid as a substrate and five different amino ester at room temperature with basic media (triethylamine). The products were obtained with a good yield ranging from 60 to 80 % and were structurally characterized by 1H and 13C NMR spectroscopy and mass spectrometry. The antibacterial activities of the synthesized compounds have been evaluated against 9 strains of bacteria and compared to references (erythromycin, ofloxacin, ticarcillin, oxacillin, ampicillin, norfloxaci

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14

Asiri, Abdullah M., Hassan M. Faidallah, Abdulrahman O. Al-Youbi, Khalid A. Alamry, and Seik Weng Ng. "4-(4-Bromophenyl)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile." Acta Crystallographica Section E Structure Reports Online 67, no. 9 (2011): o2469. http://dx.doi.org/10.1107/s1600536811033885.

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15

Asiri, Abdullah M., Hassan M. Faidallah, Abdulrahman O. Al-Youbi, Khalid A. Alamry, and Seik Weng Ng. "4-(4-Methoxyphenyl)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile." Acta Crystallographica Section E Structure Reports Online 67, no. 9 (2011): o2470. http://dx.doi.org/10.1107/s1600536811033897.

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16

Parekh, H. P., M. H. Chauhan, N. L. Solanki, and V. H. Shah. "A Clean, Benign, Energy Efficient One-Pot Multicomponent Synthesis and Bio-evaluation of Novel [1,2,4]Triazolo[1,5-a]quinolines." Asian Journal of Organic & Medicinal Chemistry 6, no. 2 (2021): 111–15. http://dx.doi.org/10.14233/ajomc.2021.ajomc-p322.

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In present work, a series of novel [1,2,4]triazolo[1,5-a]quinoline derivatives (HP-101-110) have been synthesized using multi-component reaction at room temperature in the presence of ammonium chloride as mild, cost effective green catalyst along with water as eco-friendly green solvent. The synthesis of 1,2,4-triazolo[1,5-a]quinolines (HP-101-110) was achieved by two step process. In first step, diversified Hantzsch pyridine reaction of an appropriate aromatic aldehyde, malononitrile, dimedone and benz hydrazide using ethanol as a solvent gives N-(2-amino-3-cyano-7,7-dimethyl-5-oxo-4-phenyl-5

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17

Donati, C., WK Janowski, RH Prager, MR Taylor, and LM Vilkins. "Base Catalyzed Rearrangement of Isoxazolinyl Heterocycles: Synthesis of Annelated Pyrimidines." Australian Journal of Chemistry 42, no. 12 (1989): 2161. http://dx.doi.org/10.1071/ch9892161.

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The rearrangement of a number of ethyl 2-(heterocyclic)-5-oxo-2,5-dihydroisoxazole-4-carb-oxylates by mild base is described, leading to new syntheses of the pyrimido [2,1-a] isoquinoline, pyrimido [1,2-a]quinoline, pyrimido [2,1-b] benzothiazole , pyrirnido [1,2-a] pyrimidine, pyrimido [1,2-b]pyridazine and pyrimido [1,2-c] quinazoline ring systems. A mechanism is suggested, and X-ray crystallographic evidence presented for the structure of one of the products, ethyl 2-hydroxy-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate.

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18

Asiri, Abdullah M., Hassan M. Faidallah, Abdulrahman O. Al-Youbi, Khalid A. Alamry, and Seik Weng Ng. "2-Oxo-4-phenyl-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile." Acta Crystallographica Section E Structure Reports Online 67, no. 9 (2011): o2468. http://dx.doi.org/10.1107/s1600536811033873.

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19

Charris, Jaime, Arthur Barazarte, José Domínguez, and Neira Gamboa. "Microwave-assisted synthesis of quinolones and 4H-1,4-benzo thiazine 1,1-dioxides." Journal of Chemical Research 2005, no. 1 (2005): 27–28. http://dx.doi.org/10.3184/0308234053431158.

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A rapid method for the preparation of N-aryl-2-methylthio-4-oxo-1,4-dihydro quinoline-3-carbonitriles (2a–e) and N-aryl-3-methylthio-4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxides (2f–o) is reported. The cyclization is accelerated by microwave irradiation under solvent free conditions in the presence of K2CO3.

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20

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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21

Sekar, K., S. Parthasarathy, K. J. Prabahar, and V. T. Ramakrishnan. "Structure of 1,8-dimethyl-4-oxo-1,2,2a,3,4,5-hexahydrocyclopenta[de]quinoline." Acta Crystallographica Section C Crystal Structure Communications 49, no. 1 (1993): 97–99. http://dx.doi.org/10.1107/s0108270192004219.

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22

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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23

Milata, Viktor, Dušan Ilavský, Igor Goljer, Ján Leško, Marc Chahinian, and Erica Henry-Basch. "4-Aminoethylene derivatives of 2-methylbenzotriazole." Collection of Czechoslovak Chemical Communications 55, no. 4 (1990): 1038–48. http://dx.doi.org/10.1135/cccc19901038.

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N-Methylation of 4(7)-nitrobenzotriazole (I) afforded a mixture of three isomers; one of them, 4-nitro-2-methylbenzotriazole (II) could easily be isolated. Catalytical hydrogenation of II led to the corresponding amine which in turn, afforded products of nucleophilic substitution IVa-IVi on reaction with alkoxymethylene derivatives IIIa-IIIi. Thermal cyclocondensation of IVi yielded 7-ethoxycarbonyl-6,9-dihydro-6-oxo-2-methyl-2H-triazolo[4,5-h]quinoline (V). The structure of all products was deduced from the IR, UV, 1H and 13C NMR spectral data.

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24

Acosta Quintero, Lina M., Alirio Palma, Justo Cobo, and Christopher Glidewell. "A concise and efficient concurrent synthesis of 6,11-dihydrodibenzo[b,e]azepines and 5,6,11,12-tetrahydrodibenzo[b,f]azocines and their conversion to 4-oxo-8,13-dihydro-4H-benzo[5,6]azepino[3,2,1-ij]quinoline-5-carboxylates and N-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocines: synthetic sequence, spectroscopic characterization and the structures of two products." Acta Crystallographica Section C Structural Chemistry 75, no. 6 (2019): 650–56. http://dx.doi.org/10.1107/s2053229619005746.

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Reaction of 2-allyl-N-benzyl-4-fluoroaniline or 2-allyl-N-benzyl-4-chloroaniline with 98% sulfuric acid leads to the concurrent formation of halogeno-substituted 11-ethyl-6,11-dihydrodibenzo[b,e]azepines, (II), and halogeno-substituted 11-methyl-5,6,11,12-tetrahydrodibenzo[b,f]azocines, (III), in each case in (II):(III) molar ratios of ca 2:1. Further reaction of (II) leads to ethyl 13-ethyl-2-halogeno-4-oxo-8,13-dihydro-4H-benzo[5,6]azepino[3,2,1-ij]quinoline-5-carboxylate, while acetylation of (III) gives the corresponding N-acetyl derivatives. The dibenzo[b,e]azepine and dibenzo[b,f]azocine

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25

Ghorab, Mostafa M., and Mansour S. Alsaid. "Anti-breast cancer activity of some novel quinoline derivatives." Acta Pharmaceutica 65, no. 3 (2015): 271–83. http://dx.doi.org/10.1515/acph-2015-0030.

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Abstract To discover new bioactive lead compounds for medicinal purposes, 2-cyano-3-(4-substituted)-N-(quinolin-3-yl) acrylamide derivatives 2–24, chromenes 25, 26 and benzochromenes 27, 28 were synthesized. The structures of the newly synthesized compounds were confirmed by elemental analyses, IR, 1H NMR and 13C NMR spectroscopies. In addition, the structure of compound 1 was confirmed through X-ray crystallography. All the newly synthesized compounds were evaluated for their cytotoxic activity against the breast cancer cell line MCF7. The corresponding 2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N

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26

Abadleh, Mohammed M., Tawfiq Arafat, Luay Abu-Qatouseh, Mustafa M. El-Abadelah, Firas F. Awwadi, and Wolfgang Voelter. "Facile synthesis of model 2,4-diaryl-1,3,4-thiadiazino[5,6-h]fluoroquinolones." Zeitschrift für Naturforschung B 74, no. 6 (2019): 507–12. http://dx.doi.org/10.1515/znb-2019-0023.

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AbstractA Selected set of 2,4-diaryl-7-oxo-1,2,4-thiadiazino[5,6-h]quinoline-8-carboxylic acids 6a–e has been prepared via reaction of the parent 7-chloro-8-nitro-10-cyclopropyl-6-fluoroquinolone 4 with the appropriate N′-(aryl)benzothiohydrazide 5a–e in presence of triethylamine. Structures of the new heterocyclics 6a–e are supported by spectral data and confirmed by single-crystal X-ray crystallography for 6a.

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27

Torii, Sigeru, Hiroshi Okumoto, and Long He Xu. "Palladium-catalyzed carbonylation to form 2-substituted 1,4-dihydro-4-oxo-quinoline." Tetrahedron Letters 32, no. 2 (1991): 237–40. http://dx.doi.org/10.1016/0040-4039(91)80864-3.

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28

Asiri, Abdullah M., Hassan M. Faidallah, Abdulrahman O. Al-Youbi, Khalid A. Alamry, and Seik Weng Ng. "2-Oxo-4-(thiophen-2-yl)-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile." Acta Crystallographica Section E Structure Reports Online 67, no. 9 (2011): o2472. http://dx.doi.org/10.1107/s1600536811033915.

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29

Gaber, Ahmed, Walaa F. Alsanie, Majid Alhomrani, Abdulhakeem S. Alamri, Ibrahim M. El-Deen, and Moamen S. Refat. "Synthesis and Characterization of Some New Coumarin Derivatives as Probable Breast Anticancer MCF-7 Drugs." Crystals 11, no. 5 (2021): 565. http://dx.doi.org/10.3390/cryst11050565.

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This study aimed to synthesize quinolinone derivatives and investigate their cytotoxic activity. The compound 1-azacoumarin-3-carboxylic acid (2-oxo-1H-quinoline-3-carboxylic acid) was obtained via the cyclocondensation of 2-hydroxybenzaldehyde with diethyl malonate in base catalyst to give ethyl coumarin-3-carboxylate, followed by the ammonolysis of ester (ethyl coumarin-3-carboxylate) with ammonia in the presence of anhydrous potassium carbonate. Treatment of 2-oxo-1H-quinoline-3-carboxylic acid with acetic anhydride, cinnamaldehyde, cinnamic acid and methyl 5-phenyl-2-cyano-2,4-pentadienoat

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30

Farrayeh, Batool A., Mustafa M. El-Abadelah, Jalal A. Zahra, Salim F. Haddad, and Wolfgang Voelte. "Heterocycles [h]-Fused onto 4-Oxoquinoline-3-carboxylic Acid. Part X [1]. Synthesis and X-Ray Structure of a Model 4- Oxo[1,4]benzoxazepino[2,3-h]quinoline-3-carboxylic Ester." Zeitschrift für Naturforschung B 68, no. 2 (2013): 187–94. http://dx.doi.org/10.5560/znb.2013-2270.

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Direct interaction of salicylaldehyde oxyanion with ethyl 7-chloro-8-nitro-4-oxoquinoline-3- carboxylate (2) delivered the respective 7-(2-formyl-phenoxy)-8-nitro-4-oxoquinoline-3-carboxylic ester 3. Reductive cyclization of 3 furnished the corresponding 4-oxo-[1,4]benzoxazepino[2,3- h]quinoline-3-carboxylic ester 5. Acid-catalyzed hydrolysis of the esters 3/5 produced the respective acids 4/6. Structural assignments for the new compounds 3 - 6 are supported by microanalytical and spectral (IR, HRMS, NMR) data and confirmed by X-ray structure determination for compound 5. Interestingly, compou

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31

Ukrainets, Igor, Mykola Golik, Lyudmila Sidorenko, et al. "The Study of the Structure—Diuretic Activity Relationship in a Series of New N-(Arylalkyl)-6-hydroxy-2-methyl-4-oxo-2,4-dihydro-1H-pyrrolo-[3,2,1-ij]quinoline-5-carboxamides." Scientia Pharmaceutica 86, no. 3 (2018): 31. http://dx.doi.org/10.3390/scipharm86030031.

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In accordance with the principles of “me-too” technique, the preparative method for obtaining has been proposed, and the synthesis of a large series of new N-(arylalkyl)-6-hydroxy-2-methyl-4-oxo-2,4-dihydro-1H-pyrrolo[3,2,1-ij]quinoline-5-carboxamides as structurally close analogs of tricyclic pyrrolo- and pyridoquinoline diuretics has been carried out. All target compounds were obtained with high yields and purity by amidation of ethyl ester of the corresponding 2-methyl-pyrroloquinoline-5-carboxylic acid with arylalkylamines in boiling ethanol. Their structure was confirmed by the data of el

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32

Ma, Juan, and Guo-Hua Gong. "Discovery of Novel 3,4-Dihydro-2(1H)-Quinolinone Sulfonamide Derivatives as New Tubulin Polymerization Inhibitors with Anti-Cancer Activity." Molecules 27, no. 5 (2022): 1537. http://dx.doi.org/10.3390/molecules27051537.

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In this paper, a small series of novel quinoline sulfonamide derivatives was synthesized, and their structure of the target compounds were confirmed by 1H NMR and MS. The screening of the news target compounds’ in vitro cytotoxic activities against tumor cell lines by the MTT method was performed. Among them, compound D13 (N-(4-methoxybenzyl)-2-oxo-N-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydroquinoline-6-sulfonamide exhibited the strongest inhibitory effect on the proliferation of HeLa (IC50: 1.34 μM), and this value correlated well with the inhibitory activities of the compound against tubuli

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33

Chinh, Pham The, Pham Thi Tham, Duong Huong Quynh, et al. "Synthesis and Cytotoxic Activity of Several Novel N-Alkyl-Plinabulin Derivatives With Aryl Group Moieties." Natural Product Communications 16, no. 4 (2021): 1934578X2110100. http://dx.doi.org/10.1177/1934578x211010040.

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Seven novel N-alkyl-plinabulin derivatives with aryl groups moieties (nitroquinoline, 1,4-dihydroquinoline, 4-methoxybenzene, and 4-chlorobenzene) have been synthesized via aldol condensation and alkylation in one-pot, and tested for their cytotoxicity against 4 cancer cell lines (KB, HepG2, Lu, and MCF7). Compounds ( Z)−3-((6,8-dimethyl-4-oxo-1,4-dihydroquinolin-2-yl)methylene)−6-(( Z)−4-methoxybenzylidene)−1-(prop-2-yn-1-yl)piperazine-2,5-dione (5a), ( Z)−6-(( Z)−4-methoxybenzylidene)−1-(prop-2-yn-1-yl)−3-((1,6,8-trimethyl-4-oxo-1,4-dihydroquinolin-2-yl)methylene)piperazine-2,5-dione (5b), a

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34

Asiri, Abdullah M., Hassan M. Faidallah, Abdulrahman O. Al-Youbi, Khalid A. Alamry, and Seik Weng Ng. "4-(1,3-Benzodioxol-5-yl)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile." Acta Crystallographica Section E Structure Reports Online 67, no. 9 (2011): o2471. http://dx.doi.org/10.1107/s1600536811033903.

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35

Dawe, Louise N., Abeer Ahmed, and Mohsen Daneshtalab. "4-Oxo-1,4-dihydrobenzo[h][1,3]thiazeto[3,2-a]quinoline-1,3-dicarboxylic acid." Acta Crystallographica Section E Structure Reports Online 67, no. 2 (2011): o529. http://dx.doi.org/10.1107/s1600536811003333.

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36

Nugraha, Yuda Prasetya, Haruki Sugiyama, and Hidehiro Uekusa. "Ciprofloxacin salt and salt co-crystal with dihydroxybenzoic acids." Acta Crystallographica Section E Crystallographic Communications 78, no. 3 (2022): 259–63. http://dx.doi.org/10.1107/s2056989022001177.

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The crystal structure of two multi-component crystals of ciprofloxacin [systematic name: 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)quinoline-3-carboxylic acid], a fluoroquinolone antibiotic, namely, ciprofloxacin 2,6-dihydroxybenzoate salt, C17H19FN3O3 +·C7H5O4 −, (I), and ciprofloxacin hydrochloride–3,5-dihydroxybenzoic–water (1/1/1), C17H19FN3O3 +·Cl−·C7H6O4·H2O, (II), were determined. In (I) and (II), the ciprofloxacin cations are connected via head-to-tail N—H...O hydrogen bonding. Both structures show an alternating layered arrangement between ciprofloxacin and dihydroxybenzoic acid.

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37

Wang, Qian-Qian, Da-Xiang Wang, and Qian-Qian Liu. "Redetermination of methyl 4-(4-chlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C20H22ClNO3." Zeitschrift für Kristallographie - New Crystal Structures 233, no. 5 (2018): 837–38. http://dx.doi.org/10.1515/ncrs-2018-0044.

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38

Rádl, Stanislav, Viktor Zikán, and František Šmejkal. "Syntheses of 1, 2, and 9-methyl derivatives of 4,9-dihydro-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline and their antiviral activity." Collection of Czechoslovak Chemical Communications 50, no. 5 (1985): 1057–63. http://dx.doi.org/10.1135/cccc19851057.

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The paper describes syntheses of 4,9-dihydro-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline (Ia), its 1-methyl derivative (Ib), 2-methyl derivative (IIa), 9-methyl derivative (Ic), 1,9-dimethyl derivative (Id) and 2,9-dimethyl derivative (IIb). Sodium salts of compounds Ia, Ib, Ic and IIa were methylated with methyl iodide in dimethylformamide at room temperature, compounds Id and IIb were demethylated with pyridine hydrochloride. The compounds prepared were tested for antiviral activity in vivo in mice against influenza virus A2-Hongkong and the Encephalomyocarditis virus.

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39

Zhuravleva, Yulia A., Anatolij V. Zimichev, Margarita N. Zemtsova, Victor B. Rybakov, and Yurij N. Klimochkin. "Methyl 4-methyl-2-oxo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline-6-carboxylate." Acta Crystallographica Section E Structure Reports Online 65, no. 8 (2009): o2059. http://dx.doi.org/10.1107/s1600536809029948.

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40

Edmont, Dolorès, and Jacques Chenault. "A Convenient Selective N-Alkylation of 4-Oxo-1,4-dihydro-2-quinoline Carboxylic Acid." Synlett 2001, no. 06 (2001): 0833–35. http://dx.doi.org/10.1055/s-2001-14588.

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41

Gronowitz, Salo, and Géza Timari. "A New method for the synthesis of 4-oxo-4,5-dihydrofuro[3,2-c]quinoline." Journal of Heterocyclic Chemistry 27, no. 4 (1990): 1159–60. http://dx.doi.org/10.1002/jhet.5570270465.

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42

HERNANDEZ-QUIROZ, Teresa, Simon HERNÁNDEZ-ORTEGA, and Manuel SORIANO-GARCÍA. "Crystal Structure of 1-Ethyl-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinoline Carboxylic Acid (Rosoxacin)." Analytical Sciences 14, no. 3 (1998): 637–39. http://dx.doi.org/10.2116/analsci.14.637.

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43

Meng, Jing, Hai-Yu Zhou, and Feng Sui. "Crystal structure of methyl 2,7,7-trimethyl-4-(4-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C20H22N2O5." Zeitschrift für Kristallographie - New Crystal Structures 232, no. 4 (2017): 527–28. http://dx.doi.org/10.1515/ncrs-2016-0282.

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44

Li, Da, Yan Zhou, Li Zhao, and Hua Zhang. "Crystal structure of methyl 4-(4-isopropylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C23H29NO3." Zeitschrift für Kristallographie - New Crystal Structures 234, no. 1 (2018): 35–36. http://dx.doi.org/10.1515/ncrs-2018-0111.

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45

Ukrainets, I. V., L. V. Sidorenko, O. V. Gorokhova, N. L. Bereznyakova, and S. V. Shishkina. "4-hydroxy-2-quinolones. 109. Alkylation of 4-substituted ethyl 2-oxo-1,2-dihydro-quinoline-3-carboxylates." Chemistry of Heterocyclic Compounds 42, no. 10 (2006): 1296–300. http://dx.doi.org/10.1007/s10593-006-0238-4.

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46

El-Sheref, Essmat M., Ashraf A. Aly, Aboul-Fetouh E. Mourad, Alan B. Brown, Stefan Bräse, and Momtaz E. M. Bakheet. "Synthesis of pyrano[3,2-c]quinoline-4-carboxylates and 2-(4-oxo-1,4-dihydroquinolin-3-yl)fumarates." Chemical Papers 72, no. 1 (2017): 181–90. http://dx.doi.org/10.1007/s11696-017-0269-6.

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47

SRIVATAVA, N., and A. KUMAR. "Synthesis of substituted-4-oxo-1, 4-dihydro-3-[1-oxo-2-hydrazino-3-{ptoluenesulfon}] quinoline Derivatives and their Biological Activity Against Bacterial Infections." Oriental Journal Of Chemistry 29, no. 2 (2013): 507–11. http://dx.doi.org/10.13005/ojc/290216.

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48

Bremner, JB, and W. Jaturonrusmee. "Synthesis of the 3-Aza[9]metacyclophane System by Oxidative Cleavage of a 3-Aza[6](1,7)naphthalenophane Derivative." Australian Journal of Chemistry 44, no. 1 (1991): 135. http://dx.doi.org/10.1071/ch9910135.

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Reaction of 10,11-dimethoxy-1,4,5,6-tetrahydro-7,9-ethano-3-benzazecine-3(2H)- carbonitrile (3) with ozone at -78°, followed by destruction of the ozonide with dimethyl sulfide, gave, in 82% yield, 15-formyl-12,13-dimethoxy-8-oxo-4-azabicyclo[9.3.1]pentadeca-1(15), 11,13-triene-4-carbonitrile (4), a representative of the new 3-aza[9] metacyclophane system. The precursor (3) was obtained by cyanogen bromide-induced eliminative ring destruction of 8,9-dimethoxy-2,3,5,6,10,11,11a,11b-octahydro-1H-benzo[de] pyrido [3,2,1-ij] quinoline (2) in 96% yield. An attempt to make the analogous precursor fo

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49

Kubicki, Maciej, Teresa Borowiak, Stanis?aw Boryczka, and Andrzej M�slankiewicz. "Molecular and crystal structure of 1-methyl-3-[(3-methylthio-4-quinolyl)thio]-1,4-dihydro-4-oxo-quinoline." Journal of Crystallographic and Spectroscopic Research 21, no. 6 (1991): 687–91. http://dx.doi.org/10.1007/bf01179914.

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50

M. AL-AJELY, Harith. "GREEN SYNTHESIS OF NEW HYDRAZONE DERIVATIVES." MINAR International Journal of Applied Sciences and Technology 4, no. 3 (2022): 530–35. http://dx.doi.org/10.47832/2717-8234.12.50.

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Novel set of hippuric hydrazones (6-9) bearing indole and quinoline moieties were synthesized in three steps following the protocol of microwave irradiation and solvent-free conditions. The first series were synthesized by irradiate ethyl hippurate (3) with 1H-indole-6-carbaldehyde (4) under solvent-free conditions. The second series were synthesized by irradiate ethyl hippurate (3) with substituted 2-oxo-1,2-dihydroquinoline-3-carbaldehyde (5) under solventfree conditions. This work aims to develop new synthetic route of hippuric hydrazones which may possess a promising biological activities

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