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Journal articles on the topic 'Quinoline – Synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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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

Xuan, Duc Dau. "Recent Progress in the Synthesis of Quinolines." Current Organic Synthesis 16, no. 5 (2019): 671–708. http://dx.doi.org/10.2174/1570179416666190719112423.

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Background: Quinoline-containing compounds present in both natural and synthetic products are an important class of heterocyclic compounds. Many of the substituted quinolines have been used in various areas including medicine as drugs. Compounds with quinoline skeleton possess a wide range of bioactivities such as antimalarial, anti-bacterial, anthelmintic, anticonvulsant, antiviral, anti-inflammatory, and analgesic activity. Due to such a wide range of applicability, the synthesis of quinoline derivatives has attracted a lot of attention of chemists to develop effective methods. Many known me

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3

Sonawane, Amol D., Dinesh R. Garud, Taro Udagawa, and Mamoru Koketsu. "Synthesis of thieno[2,3-b]quinoline and selenopheno[2,3-b]quinoline derivativesviaiodocyclization reaction and a DFT mechanistic study." Organic & Biomolecular Chemistry 16, no. 2 (2018): 245–55. http://dx.doi.org/10.1039/c7ob02523h.

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Thieno[2,3-b]quinoline and selenopheno[2,3-b]quinoline derivatives were synthesized by the regioselective iodocyclization reaction of 3-alkynyl-2-(methylthio)quinolines and 3-alkynyl-2-(methylseleno)quinolines.

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4

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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5

Singhal, Anchal, Pratibha Kumari, and Kharu Nisa. "Facile One-Pot Friedlander Synthesis of Functionalized Quinolines using Graphene Oxide Carbocatalyst." Current Organic Synthesis 16, no. 1 (2019): 154–59. http://dx.doi.org/10.2174/1570179415666181002114621.

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Background: Quinolines represent an important class of bioactive molecules which are present in various synthetic drugs, biologically active natural compounds and pharmaceuticals. Quinolines find their potential applications in various chemical and biomedical fields. Thereby, the demand for more efficient and simple methodologies for the synthesis of quinolines is growing rapidly. </P><P> Objective: The green one-pot Friedlander Synthesis of Functionalized Quinolines has been demonstrated by using graphene oxide as a carbocatalyst. </P><P> Method: The graphene oxide cat

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6

Rocha, Djenisa H. A., Vasco F. Batista, Emanuel J. F. Balsa, Diana C. G. A. Pinto, and Artur M. S. Silva. "Chromene- and Quinoline-3-Carbaldehydes: Useful Intermediates in the Synthesis of Heterocyclic Scaffolds." Molecules 25, no. 17 (2020): 3791. http://dx.doi.org/10.3390/molecules25173791.

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Chromenes and quinolines are recognized as important scaffolds in medicinal chemistry. Herein, the efficient use of chromene- and quinoline-3-carbaldehydes to synthesize other valuable heterocycles is described. These carbaldehydes are obtained in excellent yields through the Vilsmeyer-Haack reaction of flavanones and azaflavanones. Protocols towards the synthesis of new heterocycles, such as 3H-chromeno[3–c]quinolines, (Z/E)-2-aryl-4-chloro-3-styryl-2H-chromenes, and (E)-2-aryl-4-chloro-3-styrylquinoline-1(2H)-carbaldehydes were established. Altogether, we demonstrate the value of chromene- a

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7

Peng, Jin-Bao, Bo Chen, Xinxin Qi, Jun Ying, and Xiao-Feng Wu. "Palladium-catalyzed synthesis of quinolin-2(1H)-ones: the unexpected reactivity of azodicarboxylate." Organic & Biomolecular Chemistry 16, no. 10 (2018): 1632–35. http://dx.doi.org/10.1039/c8ob00199e.

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8

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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9

Mandal, Susanta, Samuzal Bhuyan, Saibal Jana, Jagir Hossain, Karan Chhetri, and Biswajit Gopal Roy. "Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinoline N-oxides." Green Chemistry 23, no. 14 (2021): 5049–55. http://dx.doi.org/10.1039/d1gc01460a.

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Quinolin-2(1H)-ones are prevalent in natural products and pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides.

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10

Abdel Hafez, Ali A., Ahmed A. Geies, Zeinab A. Hozien, and Zarif H. Khalil. "Synthesis of Some New 8-Quinolinyloxy-5-sulfonamide Derivatives." Collection of Czechoslovak Chemical Communications 59, no. 4 (1994): 957–77. http://dx.doi.org/10.1135/cccc19940957.

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5-Sulfonyl-8-quinolinol was used for the synthesis of various derivatives. This attempt was directed by knowledge that 8-quinolinol was utilized in the synthesis of biologically active heterocycles as bactericides, fungicides and bioregulators. The biological and pesticidal activity of 1,3,4-oxadiazoles, as well as the pharmacological interest of the quinoline moiety, are well known, too.

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11

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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12

Yang, Jinfei, Xiao Meng, Kai Lu, et al. "Acid-promoted iron-catalysed dehydrogenative [4 + 2] cycloaddition for the synthesis of quinolines under air." RSC Advances 8, no. 55 (2018): 31603–7. http://dx.doi.org/10.1039/c8ra06826g.

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An acid-promoted iron-catalysed dehydrogenative [4 + 2] cycloaddition reaction was developed for the synthesis of quinolines using air as a terminal oxidant. Various quinoline derivatives were obtained, and no other byproducts besides water.

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13

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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14

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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15

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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16

Wang, Cheng-Chung, Chieh-Kai Chan, and Chien-Yu Lai. "Environmentally Friendly Nafion-Mediated Friedländer Quinoline Synthesis under Microwave Irradiation: Application to One-Pot Synthesis of Substituted Quinolinyl Chalcones." Synthesis 52, no. 12 (2020): 1779–94. http://dx.doi.org/10.1055/s-0039-1690088.

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An efficient and eco-friendly synthetic route for Friedländer quinoline synthesis of polysubstituted quinolines is described. This green chemical method starts from various 2-aminobenzophenones and mono- or dicarbonyl synthons and uses reusable Nafion NR50 material as a solid catalyst in ethanol under microwave irradiation. The protocol has a high generality of functional groups and provides the desired quinolines in good to excellent yields. Some structures were confirmed by single-crystal X-ray diffraction analysis.

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17

Abd El-Aal, Hassan A. K., and Talaat I. El-Emary. "Synthesis of Tetracyclic Fused Quinolines via a Friedel–Crafts and Beckmann Ring Expansion Sequence." Australian Journal of Chemistry 72, no. 12 (2019): 945. http://dx.doi.org/10.1071/ch19363.

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An efficient protocol for the construction of tetracyclic fused quinolines (pyrazole-fused azepino-, azocino-, and azonino[3,2-b]quinolinones) via consecutive Friedel–Crafts and Beckmann reactions has been developed. The key steps in the syntheses of these new molecular scaffolds involve acid-mediated cyclization of 2-(pyrazol-3-yl)quinoline based carboxylic acids 6a–c, 8, and 12 to ketones 13a–e, followed by Beckmann rearrangements of the corresponding oximes 14a–e to provide the tetracyclic-fused quinoline skeletons 15a–e. Structures of synthesised compounds without stereochemical implicatio

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18

Abdel Hafez, Ali A. "Synthesis of Some Heterocyclic Sulfones Related to Quinolinol." Collection of Czechoslovak Chemical Communications 58, no. 9 (1993): 2222–26. http://dx.doi.org/10.1135/cccc19932222.

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It is well known that pyrazolone derivatives possess antifungal and antibacterial activities. Pyrazole and isoxazole derivatives are widely used in medicinal chemistry. In continuation of our work on the synthesis of heterocycles containing the quinoline moiety we synthesized different heterocyclic sulfones related to quinolinol.

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19

Arya, Anju, Akhil Mahajan, and Tejpal Singh Chundawat. "Microwave-assisted One-pot Synthesis of 2-Substituted Quinolines by Using Palladium Nanoparticles as a Catalyst developed from Green Alga Botryococcus braunii." Current Organocatalysis 7, no. 2 (2020): 82–88. http://dx.doi.org/10.2174/2213337206666190625112833.

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Background: Quinoline is a type of N-based organic heterocyclic biologically active compound. Quinolines have grasped the interest of scientists because of their wide scope of applications. Several methods have been developed for the synthesis of quinoline and its derivatives. In this study, a new, efficient, simple, one-pot synthesis of the substituted quinolines was developed by using palladium nanoparticles as a catalyst. Methods: Catalyst synthesized by algal extract of green alga Botryococcus braunii and palladium acetate solution, and characterized by different instrumental techniques li

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20

Choudhury, Sudip, Satya Paul, K. Majumdar, and Siddique Anwar. "Copper(I) Iodide Supported Synthesis of Coumarin- and Quinolone-Annulated 2-Aminothiazoles." Synlett 26, no. 08 (2015): 1039–44. http://dx.doi.org/10.1055/s-0034-1380272.

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An efficient and convenient method for the synthesis of coumarin- and quinolone-annulated 2-aminothiazoles is reported. The fused ring 2-aminothiazoles were synthesized from substituted coumarin/quinoline and phenylisothiocyanates in the presence of CuI, DABCO, and 1,10-phenanthroline. Both the rings in coumarin moiety supported the annulation by this method.

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21

Abirami, M., S. Thamarai Selvi, V. Nadaraj, and T. Daniel Thangadurai. "Synthesis and Biological Screening of Pyrano[2,3-b]quinoline Derivatives." Asian Journal of Chemistry 33, no. 8 (2021): 1791–95. http://dx.doi.org/10.14233/ajchem.2021.23253.

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Herein, a novel ionic liquid catalyzed synthesis of 3-acetylpyrano[2,3-b]quinolin-2(1H)-ones (3a-e) from substituted 3-formylquinolin-2(1H)-ones (1a-e) and ethyl acetoacetate (2) through Knoevenagel condensation is reported. We have perceived the application of microwave irradiation and ionic liquid for carrying out pollution free and ecofriendly chemical reactions. These reactions proceeded much faster in ionic liquid medium under microwave irradiation. The structures of quinoline derivatives (3a-e) were characterized by standard physico-chemical techniques. The synthesized quinoline derivati

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22

Mekheimer, Ramadan Ahmed, Galal Hamza Elgemeie, and Thomas Kappe. "Synthesis of some novel azido- and tetrazoloquinoline-3-carbonitriles and their conversion into 2,4-diaminoquinoline-3-carbonitriles." Journal of Chemical Research 2005, no. 2 (2005): 82–85. http://dx.doi.org/10.3184/0308234054497100.

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23

Abd El-Aal, Hassan A. K., and Talaat I. El-Emary. "Corrigendum to: Synthesis of Tetracyclic Fused Quinolines via a Friedel–Crafts and Beckmann Ring Expansion Sequence." Australian Journal of Chemistry 72, no. 12 (2019): 990. http://dx.doi.org/10.1071/ch19363_co.

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An efficient protocol for the construction of tetracyclic fused quinolines (pyrazole-fused azepino-, azocino-, and azonino[3,2-b]quinolinones) via consecutive Friedel–Crafts and Beckmann reactions has been developed. The key steps in the syntheses of these new molecular scaffolds involve acid-mediated cyclization of 2-(pyrazol-3-yl)quinoline based carboxylic acids 6a–c, 8, and 12 to ketones 13a–e, followed by Beckmann rearrangements of the corresponding oximes 14a–e to provide the tetracyclic-fused quinoline skeletons 15a–e. Structures of synthesised compounds without stereochemical implicatio

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24

Öhlinger, Stefan Holger. "AN EFFICIENT SYNTHESIS OF β-(3-QUINOLINYL)-α-ALANINE". SOUTHERN BRAZILIAN JOURNAL OF CHEMISTRY 17, № 17 (2009): 1–8. http://dx.doi.org/10.48141/sbjchem.v17.n17.209.4_2009.pdf.

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A convenient synthesis for β-(3-quinolinyl)-α-alanine (4) is presented. Condensation of 2-chloro-3-chloromethylquinoline (5) with diethyl acetamidomalonate (2) gave high yield of diethyl 2-acetylamino-2-(2-chloro-3-quinolinylmethyl)- propanedionate (6), which was dehalogenated in the presence of ammonium formate and palladium/charcoal. Diethyl 2-acetamido-2-(3-quinolinylmethyl)-malonate (3) was easily converted to the amino acid. The condensation reaction between 2 and 6 is also useful for the construction of (1H)-2,3-dihydropyrrolo[2,3-b]quinoline-2,2-bis(carboxylic acid) and pyrrolo[2,3-b]qu

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25

Chen, Xinghua, Mei Peng, Hao Huang, et al. "TsOH·H2O-mediated N-amidation of quinoline N-oxides: facile and regioselective synthesis of N-(quinolin-2-yl)amides." Organic & Biomolecular Chemistry 16, no. 34 (2018): 6202–5. http://dx.doi.org/10.1039/c8ob00862k.

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An operationally simple method with 100% atom economy was developed for the synthesis of various N-(quinolin-2-yl)amides via the TsOH·H<sub>2</sub>O-mediated N-amidation of quinoline N-oxides using inexpensive and commercially available nitriles as the amidation reagents.

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26

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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27

Zhao, Min Min, Yong Hua Li, De Hong Wu, and Qing Wan. "4-(6-Quinolyloxymethyl)benzonitrile." Acta Crystallographica Section E Structure Reports Online 65, no. 6 (2009): o1261. http://dx.doi.org/10.1107/s1600536809016560.

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The title compound, C17H12N2O, was synthesized by an ether synthesis from quinolin-6-ol and 4-(bromomethyl)benzonitrile. The phenyl ring of the benzonitrile group makes a dihedral angle of 47.52 (6)° with the plane of the quinoline fragment. The crystal structure is stabilized by intermolecular C—H...π interactions between a benzene H atom of the benzonitrile group and the benzene ring of the quinoline fragment. In addition, the crystal structure also exhibits a weak intermolecular C—H...N hydrogen bond.

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28

Khidre, Rizk E., Tahah A. Ameen, and Mounir A. I. Salem. "Tetrazoloquinolines: Synthesis, Reactions, and Applications." Current Organic Chemistry 24, no. 4 (2020): 439–64. http://dx.doi.org/10.2174/1385272824666200217095341.

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This review summarizes the synthesis, reactions, and biological activities of tetrazolo[1,5-a]quinoline derivatives. These derivatives were synthesized by several methods such as i) from the reaction of 2-chloroquinoline with sodium azide ii) from diazotization 2-hydrazinylquinoline derivatives, and iii) from intramolecular cyclocondensation of 2-azidoarylidenes. Also, the chemical reactions and pharmacological activities of some tetrazoloquinolines such as tetrazolo[1,5-a]quinoline-4-carbaldehyde, 5-chlorotetrazolo[ 1,5-a]quinoline, 4-(chloromethyl)tetrazolo[1,5-a]quinoline, tetrazolo[1,5- a]

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29

Shimada, Kazuaki, Hironori Izumi, Koki Otashiro, et al. "A Novel One-step Synthesis of Quinoline-2(1H)-thiones and Selones by Treating 3-Aryl-3-(2-aminophenyl)-1-propyn-3-ols with a Base and Elemental Sulfur or Selenium." Natural Product Communications 10, no. 6 (2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000628.

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A one-step conversion of 3-aryl-3-(2-aminophenyl)-1-propyn-3-ols into quinoline-2(1 H)-thiones and quinoline-2(1 H)-selones was achieved only by treating the substrates with n-butyllithium and either elemental sulfur or selenium, respectively. The reactions were assumed to proceed through an intramolecular nucleophilic attack of the neighboring amino group to the plausible in situ generated reactive species related to chalcogenoketenes. The subsequent mCPBA oxidation of quinoline-2(1 H)-selones afforded quinolin-2(1 H)-ones in high yields.

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30

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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31

Chi, Nguyen Thi Thanh, Pham Van Thong, Truong Thi Cam Mai, and Luc Van Meervelt. "Mixed natural arylolefin–quinoline platinum(II) complexes: synthesis, structural characterization and in vitro cytotoxicity studies." Acta Crystallographica Section C Structural Chemistry 74, no. 12 (2018): 1732–43. http://dx.doi.org/10.1107/s2053229618015978.

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Five new platinum(II) complexes bearing a eugenol and a quinoline derivative, namely [η2-4-allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]-trans-dichlorido(quinoline-κN)platinum(II), [PtCl2(C15H20O4)(C9H7N)], (2), {η2-4-allyl-2-methoxy-1-[(propan-2-yloxy)carbonylmethoxy]benzene}-trans-dichlorido(quinoline-κN)platinum(II), [PtCl2(C15H19O4)(C9H7N)], (3), [η2-4-allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]chlorido(quinolin-8-olato-κ2 N,O)platinum(II), [Pt(C9H6NO)Cl(C15H20O4)], (4), {η2-4-allyl-2-methoxy-1-[(propan-2-yloxy)carbonylmethoxy]benzene}chlorido(quinolin-8-olato-κ2 N,O)platinum(I

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32

Ozturk, Turan, and Alexander McKillop. "The synthesis of pyrido(2,3,4-kl)acridine unit of some marine alkaloids." Canadian Journal of Chemistry 78, no. 9 (2000): 1158–64. http://dx.doi.org/10.1139/v00-119.

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A simple and convenient synthesis of pyrido(2,3,4-kl)acridine (1), the main skeleton of some marine alkaloids, via cyclization and intramolecular nitrene insertion, is described. The importance of the planarity of the molecule during the nitrene insertion is explained.Key words: pyridoacridine, marine alkaloids, nitrene insertion, quinoline, quinolinone.

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33

Ramasamy, A. K., V. Balasubramaniam, and K. Mohan. "Synthesis and Characterization of Substituted 4-Methoxy-1H-quinolin-2-ones." E-Journal of Chemistry 7, no. 3 (2010): 1066–70. http://dx.doi.org/10.1155/2010/317391.

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An efficient method for the synthesis of various substituted 4-methoxy-1H-quinolin-2-ones from various substituted aniline with malonic acid, phosphorous oxychloride, sodium methoxide and glacial acetic acid under different conditions is described. The title compounds were synthesized from three steps; the first step involved the synthesis of substituted 2, 4-dichloro quinoline from aniline (substituted), with malonic acid and phosphorous-oxychloride. In the second step, the substituted 2, 4 dichloro compounds was heated with freshly prepared methanolic sodium methoxide solution to give 2, 4-d

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34

Shiri, Morteza, Zahra Gholami-Koupaei, Farzaneh Bandehali-Naeini та ін. "Highly Selective Synthesis of α-Hydroxy, α-Oxy, and α-Oxo Amides by a Post-Passerini Condensation Transformation". Synthesis 52, № 21 (2020): 3243–52. http://dx.doi.org/10.1055/s-0040-1707132.

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A post-Passerini condensation transformation can be employed in the synthesis of three types of amides: α-hydroxy, α-oxy, and α-oxo amides. K2CO3 efficiently promotes the solvolysis of α-acetoxy amides to form α-hydroxy amides in methanol. 2-Acetoxy-2-(2-alkynylquinolin-3-yl)acetamides in basic methanol are cyclized to 1,3-dihydrofuro[3,4-b]quinoline-1-carboxamides via deacetylation and 5-exo-dig cyclization. Treatment of 2-hydroxy-2-[2-(phenylethynyl)quinolin-3-yl]acetamides with I2 in basic media produces pyrrolo[2,3-b]quinoline-2,3-diones. This cyclization involves intramolecular cyclizati

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Muhammad, Mehwish Hussain, Xiao-Lan Chen, Bing Yu, Ling-Bo Qu, and Yu-Fen Zhao. "Applications of H-phosphonates for C element bond formation." Pure and Applied Chemistry 91, no. 1 (2019): 33–41. http://dx.doi.org/10.1515/pac-2018-0906.

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Abstract The readily accessible and inexpensive dialkyl H-phosphonates are important building blocks for organic synthesis. This review specifically covers our recent work on the application of H-phosphonates as reactants for C–P bond formation, and as promoters for quinoline N-oxides to synthesize 2-functionalized quinolines.

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36

Yang, Yi-Qiu, Long-Zhi Ke, Gui-Fei Wang, et al. "Synthesis of N-Pyridin-2-ylmethyl and N-Quinolin-2-ylmethyl Substituted Ethane-1,2-diamines." SynOpen 01, no. 01 (2017): 0147–55. http://dx.doi.org/10.1055/s-0036-1590963.

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Two N-(2-(bis(pyridin-2-ylmethyl)amino)ethyl)quinoline-2-carboxamides and two N-(2-(bis(quinolin-2-ylmethyl)amino)ethyl)quinoline-2-carboxamides have been synthesized. These structures contain five nitrogen atoms that can form coordinate bonds with metal ions such as Mn(II) and Fe(II). An additional coordinating bond can be formed between the metal ion and a neutral molecule of nitric oxide (NO). The resultant complexes are potentially useful agents for targeted delivery of NO to in vivo biological sites such as tumors, where the NO is released upon irradiation with long-wavelength light. Init

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37

Kumar, Alleni Suman, Rathod Aravind Kumar, Vavilapally Satyanarayana, et al. "Catalyst-Free Synthesis of Novel 6-Phenyl-6H-chromeno [4, 3-b] quinoline Derivatives at RT: Their Further Structure Evaluation Leads to Potential Anti-cancer Agents." Natural Product Communications 12, no. 7 (2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200732.

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A variety of novel quinoline derivatives (6-phenyl-6 H-chromeno [4,3- b] quinoline) have been prepared by using 4-chloro-2-phenyl-2 H-chromene-3-carbaldehyde and various substituted of aromatic anilines as starting materials. This is the first example on the preparation of quinolines through this novel method. And the resulting quinoline derivatives further structure evolution is leads to an anti cancer agents. Our preliminary data of model compound (7i) on three cancer cell lines (B16F10, MCF7 and A549) suggested decent anticancer activity on two cell lines (B16F10 and MCF7) with IC50 values

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38

Tasqeeruddin, Syed, Yahya Asiri, and Jaber Abdullah Alsherhri. "An Efficient and Green Microwave-Assisted Synthesis of Quinoline DerivativesviaKnoevengal Condensation." Letters in Organic Chemistry 17, no. 2 (2020): 157–63. http://dx.doi.org/10.2174/1570178616666190618153721.

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:We have developed an efficient and green synthesis of quinoline derivatives using L-proline under Knoevenagel condensation. L-proline was found to be an efficient catalyst for the Knoevenagel condensation of substituted 2-aminoaryl ketones 1 with the active methylene compounds 2, affording quinolone derivatives 3. The reaction has been done under conventional as well as under microwave conditions. The latter procedure has been found to be much more efficient in terms of time and yield.

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39

Rádl, Stanislav. "Synthetic Studies Connected with the Preparation of 4-Cyclopropyl-7-fluoro-6-(4-methylpiperazin-1-yl)-1,2,4,9-tetrahydrothiazolo[5,4-b]quinoline-2,9-dione." Collection of Czechoslovak Chemical Communications 62, no. 5 (1997): 791–99. http://dx.doi.org/10.1135/cccc19970791.

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Target 4-cyclopropyl-7-fluoro-6-(4-methylpiperazin-1-yl)-1,2,4,9-tetrahydrothiazolo[5,4-b]quinoline-2,9-dione (5a) was obtained from 3-amino-1-cyclopropyl-6-fluoro-7-(4-methylpiperazin-1-yl)-2-mercaptoquinolin-4(1H)-one (9b). This intermediate was obtained from 3-amino-1-cyclopropyl- 6,7-difluoro-2-(methylsulfinyl)quinolin-4(1H)-one (9f) via 3-amino-1-cyclopropyl-6-fluoro-7-(4-methylpiperazin-1-yl)-2-(methylsulfinyl)quinolin-4(1H)-one (9c). Compound 9f was prepared from 2,4,5-trifluoroacetophenone (6a) in several steps. 4-Cyclopropyl-6,7-difluoro-2,3,4,9-tetrahydrothiazolo[5,4-b]quinoline-3,4-

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40

Milićević, David, Roman Kimmel, Martin Gazvoda, Damijana Urankar, Stanislav Kafka, and Janez Košmrlj. "Synthesis of Bis(1,2,3-Triazole) Functionalized Quinoline-2,4-Diones." Molecules 23, no. 9 (2018): 2310. http://dx.doi.org/10.3390/molecules23092310.

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Derivatives of 3-(1H-1,2,3-triazol-1-yl)quinoline-2,4(1H,3H)-dione unsubstituted on quinolone nitrogen atom, which are available by the previously described four step synthesis starting from aniline, were exploited as intermediates in obtaining the title compounds. The procedure involves the introduction of propargyl group onto the quinolone nitrogen atom of mentioned intermediates by the reaction of them with propargyl bromide in N,N-dimethylformamide (DMF) in presence of a potassium carbonate and the subsequent formation of a second triazole ring by copper catalyzed cyclisation reaction with

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Ma, Chen, Huanhuan Liu, and Xinfeng Wang. "Synthesis of Imidazo[1,5-a]quinolines via Metal-Free Oxidative Amination of sp3 C–H Bonds." Synthesis 50, no. 14 (2018): 2761–67. http://dx.doi.org/10.1055/s-0037-1610137.

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A novel oxidative amination of sp3 C–H bonds was developed for the efficient synthesis of imidazo[1,5-a]quinolines from readily available α-amino acids and (2-azaaryl)methanes. This domino protocol, which was established in a TBAI-TBHP oxidation system, includes transition-metal-free decarboxylation and intramolecular cyclization. This method represented a new avenue for the synthesis of N-heterocycles using 2-methylquinolines as the synthon of quinoline-2-carbaldehydes.

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Abd El-Aal, Hassan A. K. "Friedel–Crafts Chemistry. Part 48. Concise Synthesis of Condensed Azaheterocyclic [1,8]naphthyridinones, Azepino-, Azocino-, and Azoninoquinoline Systems via Friedel–Crafts Ring Closures." Australian Journal of Chemistry 70, no. 10 (2017): 1082. http://dx.doi.org/10.1071/ch17108.

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Unprecedented construction of a novel series of quinoline heteropolycycles (tetracyclic keto-analogues of [1,8]naphthyridinones, azepino-, azocino- and azonino[2,3-b]quinolinones systems) 10a–i by Friedel–Crafts cycliacylation reactions is described. Starting heterocyclic acids precursors 3a–i were prepared from easily accessible 2-chloroquinoline-3-carbaldehyde 1 via a three different synthetic pathways. Acid-catalyzed ring closures of the resulting tosylated acids were achieved under the influence of both Brønsted and Lewis acid catalysts. The present strategy enables a straightforward synth

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Smetanin, N. V., and A. V. Mazepa. "Functionalization of N-arylmaleimides by sp3 C–H bonds of hydroacridines(qinolines)." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 6 (December 2020): 165–70. http://dx.doi.org/10.32434/0321-4095-2020-133-6-165-170.

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The catalyst-free sp3 C–H functionalization of tetrahydroacridine(quinolines) derivatives has been achieved using a Michael-type reaction with N-arylmaleimides. This method enables the facile synthesis of biologically important N-aryl bearing tetrahydroacridine(quinolines) moieties in a single step with high yields. The reaction occurs under non-catalytic conditions by heating of hydroacridines(quinolines) in DMSO within 4 h at 100–1200C. The reaction between starting compounds allows synthesizing (3S/4R)-3-[(3R/4S)-9-chloroacridine(quinoline)-4-yl]-1(-N-aryl)pyrrolidine-2,5-diones with a good

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44

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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Ma, Fei-Ping, Gui-Tian Cheng, Zhi-Guo He, and Zhan-Hui Zhang. "A New and Efficient Procedure for Friedländer Synthesis of Quinolines in Low Melting Tartaric Acid-Urea Mixtures." Australian Journal of Chemistry 65, no. 4 (2012): 409. http://dx.doi.org/10.1071/ch12025.

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A general, efficient and green method for the synthesis of quinoline derivatives via the Friedländer heteroannulation reaction of 2-aminoaryl ketones and α-methylene ketones has been developed, employing low melting mixtures of L-(+)-tartaric acid and urea derivatives as an inexpensive, non-toxic, easily biodegradable reaction medium. The melt acts as both the reaction medium and catalyst, furnishing quinolines in high to excellent yields.

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46

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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47

Peerzade, Nargisbano A., Shravan Y. Jadhav, and Raghunath B. Bhosale. "Synthesis and Biological Evaluation of Some Novel Quinoline based Chalcones as Potent Antimalarial, Anti-inflammatory, Antioxidant and Antidiabetic Agents." Asian Journal of Chemistry 32, no. 4 (2020): 959–64. http://dx.doi.org/10.14233/ajchem.2020.22542.

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The objective of the present study was to synthesize a series of some novel quinoline based methoxy substituted chalcones and to evaluate their in vitro antimalarial, anti-inflammatory, antioxidant and antidiabetic activitites. The quinoline based chalcones was synthesized by condensation of 2-chloro-3-formyl qunoline with various methoxy substituted acetophenone in presence of NaOH. The Claisen-Schmidt condensation gave high yield of quinoline based chalcones. Synthesis of 2-chloro-3-formyl quinoline was carried out by Vilsmeir-Haack reaction on acetanilide and 4-methoxy acetanilide which on

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48

Corona, Paola, Sandra Piras, Michele Palomba, and Antonio Carta. "Synthesis of Linear Azolo and Pyrido Quinolines from Quinoline Derivatives." Mini-Reviews in Organic Chemistry 5, no. 4 (2008): 295–302. http://dx.doi.org/10.2174/157019308786242197.

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Rowlands, Gareth J., Rebecca J. Severinsen, Jenna K. Buchanan, et al. "Synthesis and Basicity Studies of Quinolino[7,8-h]quinoline Derivatives." Journal of Organic Chemistry 85, no. 17 (2020): 11297–308. http://dx.doi.org/10.1021/acs.joc.0c01428.

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Rimaz, Mehdi. "Two Efficient One-Pot Approaches for Regioselective Synthesis of New 3-Arylpyridazino[4,3-c]quinolin-5(6H)-ones." Australian Journal of Chemistry 68, no. 10 (2015): 1529. http://dx.doi.org/10.1071/ch15029.

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Two efficient regioselective approaches for the one-pot synthesis of 3-arylpyridazino[4,3-c]quinolin-5(6H)-one derivatives are reported, by the three-component reaction of arylglyoxal monohydrates, quinoline-2,4-diol, and hydrazinium dihydrochloride or hydrazine hydrate in ethanol and pyridine. In ethanol, the reactions were catalyzed by 1,4-diazobicyclo[2,2,2]octane. The features of both procedures are high regioselectivity, mild reaction conditions, good to high yields, and operational simplicity.

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