Log in

Relevant bibliographies by topics / Quinoline – Synthesis / Journal articles

To see the other types of publications on this topic, follow the link: Quinoline – Synthesis.

Journal articles on the topic 'Quinoline – Synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

Create a spot-on reference in APA, MLA, Chicago, Harvard, and other styles

Select a source type:

Consult the top 50 journal articles for your research on the topic 'Quinoline – Synthesis.'

Next to every source in the list of references, there is an 'Add to bibliography' button. Press on it, and we will generate automatically the bibliographic reference to the chosen work in the citation style you need: APA, MLA, Harvard, Chicago, Vancouver, etc.

You can also download the full text of the academic publication as pdf and read online its abstract whenever available in the metadata.

Browse journal articles on a wide variety of disciplines and organise your bibliography correctly.

1

Horta, Pedro, Marta S. C. Henriques, Elisa M. Brás, Fernanda Murtinheira, Fátima Nogueira, Paul M. O’Neill, José A. Paixão, Rui Fausto, and Maria L. S. Cristiano. "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 (June 27, 2017): 765–80. http://dx.doi.org/10.1515/pac-2016-1119.

Full text

Abstract:

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-iodo-4-(3-iodo-4-methylphenoxy)-quinoline-3-carboxylate, a 4-aryloxy-quinoline 3-ester formed during attempted preparation of 6-methyl-7-iodo-4-oxo-quinoline-3-carboxylate (4-oxo-quinoline 3-ester). We propose that the 4-aryloxy-quinoline 3-ester derives from 6-methyl-7-iodo-4-hydroxy-quinoline-3-carboxylate (4-hydroxy-quinoline 3-ester), the enol form of 6-methyl-7-iodo-4-oxo-quinoline-3-carboxylate. Formation of the 4-aryloxy-quinoline 3-ester confirms the impact of quinolone/hydroxyquinoline tautomerism, both on the efficiency of synthetic routes to quinolones and on pharmacologic profiles. Tautomers exhibit different cLogP values and interact differently with the enzyme active site. A structural investigation of 6-methyl-7-iodo-4-oxo-quinoline-3-carboxylate and 6-methyl-7-iodo-4-hydroxy-quinoline-3-carboxylate, using matrix isolation coupled to FTIR spectroscopy and theoretical calculations, revealed that the lowest energy conformers of 6-methyl-7-iodo-4-hydroxy-quinoline-3-carboxylate, lower in energy than their most stable 4-oxo-quinoline tautomer by about 27 kJ mol−1, are solely present in the matrix, while the most stable 4-oxo-quinoline tautomer is solely present in the crystalline phase.

APA, Harvard, Vancouver, ISO, and other styles

2

Xuan, Duc Dau. "Recent Progress in the Synthesis of Quinolines." Current Organic Synthesis 16, no. 5 (October 17, 2019): 671–708. http://dx.doi.org/10.2174/1570179416666190719112423.

Full text

Abstract:

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 methods have been expanded and improved. Furthermore, various new methods for quinoline synthesis have been established. This review will focus on considerable studies on the synthesis of quinolines date which back to 2014. Objective: In this review, we discussed recent achievements on the synthesis of quinoline compounds. Some classical methods have been modified and improved, while other new methods have been developed. A vast variety of catalysts were used for these transformations. In some studies, quinoline synthesis reaction mechanisms were also displayed. Conclusion: Many methods for the synthesis of substituted quinoline rings have been developed recently. Over the past five years, the majority of those reported have been based on cycloisomerization and cyclization processes. Undoubtedly, more imaginative approaches to quinoline synthesis will appear in the literature in the near future. The application of known methods to natural product synthesis is probably the next challenge in the field.

APA, Harvard, Vancouver, ISO, and other styles

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.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

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.

Full text

Abstract:

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-5,6,7,8- tetrahydro-quinolin-1(4H)-yl)-4-hydroxybenzamide derivatives. In the second step, synthesis of the final product 2-(4-hydroxyphenyl)-8,8-dimethyl-6-oxo-5-phenyl-6,7,8,9-tetrahydro[1,2,4]triazolo[1,5- a]-quinoline-4-carbonitriles was achieved by the intramolecular cyclization of step 1 product.The structure of all the synthesized compounds (HP101-110) has been elucidated by FT-IR, 1H & 13C NMR, mass spectral data and elemental analyses.

APA, Harvard, Vancouver, ISO, and other styles

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 (February 4, 2019): 154–59. http://dx.doi.org/10.2174/1570179415666181002114621.

Full text

Abstract:

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 catalyzed condensation reaction of 2–aminoaryl carbonyl compounds with different cyclic/ acyclic/ aromatic carbonyl compounds in methanol at 70°C affords different quinoline derivatives. </P><P> Results: The reaction has been examined in different protic and aprotic solvents and the best yield of quinoline is observed in methanol at 70°C. Conclusion: The present method of quinoline synthesis offers various advantages over other reported methods such as short reaction time, high yield of product, recycling of catalyst and simple separation procedure. The graphene oxide carbocatalyst can be easily recovered from the reaction mixture by centrifugation and then can be reused several times without any significant loss in its activity.

APA, Harvard, Vancouver, ISO, and other styles

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 (August 20, 2020): 3791. http://dx.doi.org/10.3390/molecules25173791.

Full text

Abstract:

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- and quinoline-3-carbaldehydes as building blocks.

APA, Harvard, Vancouver, ISO, and other styles

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.

Full text

APA, Harvard, Vancouver, ISO, and other styles

8

Portilla, Jaime, Jairo Quiroga, Manuel Nogueras, Jose M. de la Torre, Justo Cobo, John N. Low, and Christopher Glidewell. "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 (January 17, 2008): 72–83. http://dx.doi.org/10.1107/s0108768107065743.

Full text

Abstract:

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-methylphenyl)-10-methyl-8-phenyl-6,8-dihydro-5H-benzo[f]pyrazolo[3,4-b]quinoline, C28H23N3 (P\bar 1, Z′ = 2), 11-(4-methoxyphenyl)-10-methyl-8-phenyl-6,8-dihydro-5H-benzo[f]pyrazolo[3,4-b]quinoline, C28H23N3O (P21/c, Z′ = 4), and 11-(3,4,5-trimethoxyphenyl)-10-methyl-8-phenyl-6,8-dihydro-5H-benzo[f]pyrazolo[3,4-b]quinoline, C30H27N3O3, are reported. The crystal structures are compared with those of a number of analogues reported in the recent literature; in particular, structural comparisons are drawn within each series as the substituted pendent aryl group is varied, and between several pairs of strictly isomeric 7-aryl-benzo[h]pyrazolo[3,4-b]quinolines and 11-aryl-benzo[f]pyrazolo[3,4-b]quinolines containing the same aryl substituents within each pair. Intermolecular interactions of the C—H...π type are found in the crystal structures of both series, but π...π stacking interactions are found only in the 7-aryl-benzo[h]pyrazolo[3,4-b]quinoline series.

APA, Harvard, Vancouver, ISO, and other styles

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.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

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.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

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.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

12

Yang, Jinfei, Xiao Meng, Kai Lu, Zhihao Lu, Minliang Huang, Chengniu Wang, and Fei Sun. "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.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

13

Wantulok, Jakub, Marcin Szala, Andrea Quinto, Jacek E. Nycz, Stefania Giannarelli, Romana Sokolová, Maria Książek, and Joachim Kusz. "Synthesis, Electrochemical and Spectroscopic Characterization of Selected Quinolinecarbaldehydes and Their Schiff Base Derivatives." Molecules 25, no. 9 (April 28, 2020): 2053. http://dx.doi.org/10.3390/molecules25092053.

Full text

Abstract:

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. Additionally, Duff and Vilsmeier-Haack reactions were used in the double formylation of quinoline derivatives and their analogues benzo[h]quinolin-10-ol, 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde, 8-(dimethylamino) quinoline-5,7-dicarbaldehyde and 10-hydroxybenzo[h]quinoline-7,9-dicarbaldehyde. Four Schiff base derivatives of 2,6-diisopropylbenzenamine were prepared from selected quinoline-5-carbaldehydes and quinoline-7-carbaldehyde by an efficient synthesis protocol. Their properties have been characterized by a combination of several techniques: MS, HRMS, GC-MS, FTIR, electronic absorption spectroscopy and multinuclear NMR. The electrochemical properties of 8-hydroxy-quinoline-5-carbaldehyde, 6-(dimethylamino)quinoline-5-carbaldehyde and its methylated derivative were investigated, and a strong correlation between the chemical structure and obtained reduction and oxidation potentials was found. The presence of a methyl group facilitates oxidation. In contrast, the reduction potential of methylated compounds was more negative comparing to non-methylated structure. Calculations of frontier molecular orbitals supported the finding. The structures of 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde and four Schiff bases were determined by single-crystal X-ray diffraction measurements.

APA, Harvard, Vancouver, ISO, and other styles

14

Kamal, Ahmed, Abdul Rahim, Sd Riyaz, Y. Poornachandra, Moku Balakrishna, C. Ganesh Kumar, Syed Mohammed Ali Hussaini, B. Sridhar, and Pavan Kumar Machiraju. "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.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

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.

Full text

Abstract:

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 drugs viz., Ampicilin, Chloramphenicol, Ciprofloxacin, Norfloxacin, Griseofulvin and Nystatin at different concentrations.

APA, Harvard, Vancouver, ISO, and other styles

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 (March 19, 2020): 1779–94. http://dx.doi.org/10.1055/s-0039-1690088.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

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.

Full text

Abstract:

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 implication were confirmed by NMR and elemental analyses.

APA, Harvard, Vancouver, ISO, and other styles

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.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

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 (July 2, 2020): 82–88. http://dx.doi.org/10.2174/2213337206666190625112833.

Full text

Abstract:

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 like FTIR, SEM, and XRD. The synthesized palladium nanoparticles explored for the catalytic activity in the synthesis of quinoline derivatives by the use of 2-aminobenzyl alcohol in toluene with acetyl derivatives followed by the addition of potassium hydroxide. The formation of the product was confirmed by 1HNMR, 13C NMR, and electron ionization mass spectra. Results: The formation of palladium nanoparticles characterized by visual observation means the color change from light pale yellow to dark brown indicates the reduction of palladium ions into palladium nanoparticles. Synthesized palladium nanoparticles characterized by FTIR spectrum of the algal extract of green algae B. braunii for the presence of proteins, lipids, carbohydrates, carotenoids, vitamins and other secondary metabolites in algal extract, which function as active components for bioreduction. The morphology of the catalyst was confirmed by SEM and X-ray diffraction measurements for shape, crystalline nature and size. The synthesized palladium nanoparticles explored for the catalytic activity in the synthesis of quinoline derivatives by use of 2-aminobenzyl alcohol in toluene and added acetyl derivatives followed by the addition of potassium hydroxide. In order to establish the optimum heating method, a comparative study between conventional and microwave heating method was carried out in the presence of palladium nanoparticles as a catalyst. Conclusion: This protocol provides a convenient and practical procedure for the preparation of quinoline derivatives from 2-aminobenzyl alcohol, acetyl derivatives, potassium hydroxide and palladium nanoparticles as a catalyst. This protocol will be helpful in synthesizing other quinoline derivatives and several organic heterocycles which are used in different fields such as biological, industrial, pharmaceutical, chemical, medical, etc.

APA, Harvard, Vancouver, ISO, and other styles

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 (March 3, 2015): 1039–44. http://dx.doi.org/10.1055/s-0034-1380272.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

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.

Full text

Abstract:

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 derivatives (3a-e) were also evaluated for their in vitro antimicrobial screening on different strains of bacteria and fungi.

APA, Harvard, Vancouver, ISO, and other styles

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 (February 2005): 82–85. http://dx.doi.org/10.3184/0308234054497100.

Full text

APA, Harvard, Vancouver, ISO, and other styles

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.

Full text

Abstract:

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 implication were confirmed by NMR and elemental analyses.

APA, Harvard, Vancouver, ISO, and other styles

24

Öhlinger, Stefan Holger. "AN EFFICIENT SYNTHESIS OF β-(3-QUINOLINYL)-α-ALANINE." SOUTHERN BRAZILIAN JOURNAL OF CHEMISTRY 17, no. 17 (December 20, 2009): 1–8. http://dx.doi.org/10.48141/sbjchem.v17.n17.209.4_2009.pdf.

Full text

Abstract:

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]quinoline-2-carboxylic acid derivatives.

APA, Harvard, Vancouver, ISO, and other styles

25

Chen, Xinghua, Mei Peng, Hao Huang, Yangfan Zheng, Xiaojun Tao, Chunlian He, and Yi Xiao. "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.

Full text

Abstract:

An operationally simple method with 100% atom economy was developed for the synthesis of various N-(quinolin-2-yl)amides via the TsOH·H₂O-mediated N-amidation of quinoline N-oxides using inexpensive and commercially available nitriles as the amidation reagents.

APA, Harvard, Vancouver, ISO, and other styles

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 (November 2008): 640–41. http://dx.doi.org/10.3184/030823408x375070.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

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 (May 14, 2009): o1261. http://dx.doi.org/10.1107/s1600536809016560.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

28

Khidre, Rizk E., Tahah A. Ameen, and Mounir A. I. Salem. "Tetrazoloquinolines: Synthesis, Reactions, and Applications." Current Organic Chemistry 24, no. 4 (May 9, 2020): 439–64. http://dx.doi.org/10.2174/1385272824666200217095341.

Full text

Abstract:

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]quinoline-4-carboxylic acid, and 5-azidotetrazolo[1,5-a]quinoline were discussed.

APA, Harvard, Vancouver, ISO, and other styles

29

Shimada, Kazuaki, Hironori Izumi, Koki Otashiro, Kensuke Noro, Shigenobu Aoyagi, Yuji Takikawa, and Toshinobu Korenaga. "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 (June 2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000628.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

30

Kwak, Sang Woo, Ju Hyun Hong, Sang Hoon Lee, Min Kim, Yongseog Chung, Kang Mun Lee, Youngjo Kim, and Myung Hwan Park. "Synthesis and Photophysical Properties of a Series of Dimeric Indium Quinolinates." Molecules 26, no. 1 (December 23, 2020): 34. http://dx.doi.org/10.3390/molecules26010034.

Full text

Abstract:

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 quinoline groups. The absolute emission quantum yields (ΦPL) of compounds 1 (11.2% in THF and 17.2% in film) and 4 (17.8% in THF and 36.2% in film) with methyl substituents at the C5 position of the quinoline moieties were higher than those of the indium complexes with other substituents.

APA, Harvard, Vancouver, ISO, and other styles

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 (November 22, 2018): 1732–43. http://dx.doi.org/10.1107/s2053229618015978.

Full text

Abstract:

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(II), [Pt(C9H6NO)Cl(C15H20O4)], (5), and [η2-4-allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]chlorido(quinolin-2-carboxylato-κ2 N,O)platinum(II), [Pt(C10H6NO2)Cl(C15H20O4)], (6), have been synthesized and fully characterized spectroscopically. A single-crystal X-ray diffraction study was carried out for complexes (2) and (4)–(6). PrEug [or 4-allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene] in (2), (4) and (6), and iPrEug (the propan-2-yloxy analogue of PrEug) in (3) and (5) coordinate with PtII at the ethylenic double bond of the allyl group. In (2)–(6), the donor N atom of the amine group occupies a trans position with respect to the double bond. A comparison of the IC50 values of 0.38–29.23 µM for (2)–(6) with cisplatin, as well as other platinum(II) complexes, indicates an excellent in vitro cytotoxicity against the KB, LU, Hep-G2 and MCF-7 cancer cell lines, with the highest cytotoxic effect (IC50 = 0.38–1.99 µM) being for complexes (4) and (5) bearing a quinolin-8-olate ligand.

APA, Harvard, Vancouver, ISO, and other styles

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 (September 1, 2000): 1158–64. http://dx.doi.org/10.1139/v00-119.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

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.

Full text

Abstract:

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-dimethoxy quinoline compounds, it was then refluxed with glacial acetic acid and hydrochloric acid to give the titled compounds in the final step. The purity of the synthesized compounds was confirmed by their C, H and N analysis and the structure was analyzed on the basics of Mass, FT-IR and1H NMR.

APA, Harvard, Vancouver, ISO, and other styles

34

Shiri, Morteza, Zahra Gholami-Koupaei, Farzaneh Bandehali-Naeini, Maryam-Sadat Tonekaboni, Saeedeh Soheil-Moghaddam, Delaram Ebrahimi, Sima Karami, and Behrouz Notash. "Highly Selective Synthesis of α-Hydroxy, α-Oxy, and α-Oxo Amides by a Post-Passerini Condensation Transformation." Synthesis 52, no. 21 (June 8, 2020): 3243–52. http://dx.doi.org/10.1055/s-0040-1707132.

Full text

Abstract:

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 cyclization, dealkynylative aromatization, and oxidation of the secondary alcohol.

APA, Harvard, Vancouver, ISO, and other styles

35

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 (January 28, 2019): 33–41. http://dx.doi.org/10.1515/pac-2018-0906.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

36

Yang, Yi-Qiu, Long-Zhi Ke, Gui-Fei Wang, Shu-Yong Song, Ming-Ning Qiu, Jian-Jun Liu, and Yun-Sheng Huang. "Synthesis of N-Pyridin-2-ylmethyl and N-Quinolin-2-ylmethyl Substituted Ethane-1,2-diamines." SynOpen 01, no. 01 (March 2017): 0147–55. http://dx.doi.org/10.1055/s-0036-1590963.

Full text

Abstract:

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. Initial work involving the synthesis and characterization of these analogues is reported here.

APA, Harvard, Vancouver, ISO, and other styles

37

Kumar, Alleni Suman, Rathod Aravind Kumar, Vavilapally Satyanarayana, Elala Pravardhan Reddy, Boggu Jagan Mohan Reddy, Duddukuri Nandan Kumar, Amit Khurana, Godugu Chandraiah, and Jhillu Singh Yadav. "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 (July 2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200732.

Full text

Abstract:

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 of 14.8 and 21.32 μM, respectively. This method is operationally simple and works with a diverse range of substrates.

APA, Harvard, Vancouver, ISO, and other styles

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 (January 7, 2020): 157–63. http://dx.doi.org/10.2174/1570178616666190618153721.

Full text

Abstract:

: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.

APA, Harvard, Vancouver, ISO, and other styles

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.

Full text

Abstract:

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-dione (5b) was prepared similarly as the target compound. Treatment of 5b with N-methylpiperazine did not afford 5a but 1-cyclopropyl-6,7-difluoro-2-mercapto-3-[(4-methylpiperazin-1-yl)carbonylamino]quinolin-4(1H)-one (11). Several unsuccessful attempts to prepare compound 5a and/or some useful intermediates of its synthesis are also described.

APA, Harvard, Vancouver, ISO, and other styles

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 (September 10, 2018): 2310. http://dx.doi.org/10.3390/molecules23092310.

Full text

Abstract:

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 azido compounds. The products were characterized by 1H, 13C and 15N NMR spectroscopy. The corresponding resonances were assigned on the basis of the standard 1D and gradient selected 2D NMR experiments (1H–1H gs-COSY, 1H–13C gs-HSQC, 1H–13C gs-HMBC) with 1H–15N gs-HMBC as a practical tool to determine 15N NMR chemical shifts at the natural abundance level of 15N isotope.

APA, Harvard, Vancouver, ISO, and other styles

41

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 (May 29, 2018): 2761–67. http://dx.doi.org/10.1055/s-0037-1610137.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

42

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.

Full text

Abstract:

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 synthesis to fused tetracyclic quinolinone skeletons as demonstrated by concise and atom-economical syntheses.

APA, Harvard, Vancouver, ISO, and other styles

43

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.

Full text

Abstract:

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 yield. The structure of compounds was proved by spectral methods of analysis. The 1H NMR spectrum shows characteristic signals of protons of the CH-groups in acridine(quinoline) (3.4–3.5 ppm) and pyrrolidine (3.8–3.9 ppm) cycles. It is interesting to note that the main direction of the fragmentation is the Michael retro-reaction, which is accompanied by the elimination of 1-(2-nitrophenyl)-1H-pyrrole-2,5-dione and leads to the formation of m/z ions of starting chloroacridines(quinolines).

APA, Harvard, Vancouver, ISO, and other styles

44

Muchowski, Joseph M., and Michael L. Maddox. "Concerning the mechanism of the Friedländer quinoline synthesis." Canadian Journal of Chemistry 82, no. 3 (March 1, 2004): 461–78. http://dx.doi.org/10.1139/v03-211.

Full text

Abstract:

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 deliberately generated by other means. It is also shown that E-enones corresponding to 6, i.e., the aldol dehydration product, are converted into quinolines (e.g., 21a and 21b from 17a and 17b) under basic or acidic conditions. Such enones are not detected as intermediates in the base-induced Friedländer synthesis, even though certain congeners (17b) would be easily observable. Under acidic conditions these enones are too short lived to be detectable. Schiff bases derived from 2-aminobenzaldehyde (18a) and aldehydes or ketones can be generated under special conditions, but they show reactivity patterns different from those seen in the usual Friedländer condensations. Thus, the ytterbium-triflate-catalyzed reaction of aldehydes with 18a at room temperature in toluene generates the E-Schiff bases (33, R1 = H), from which isomeric mixtures of tetrahydroquinoline derivatives 26 are formed exclusively. At higher temperatures, the E-Schiff bases 33 are isomerized to the Z-Schiff bases 34, from which the 3-substituted quinoline derivatives 24 are formed as the major products under appropriate conditions. Also, the ytterbium-triflate-catalyzed reaction of 18a with the pyrrolidine enamines of the methyl-n-alkylketones 38a,b produces mixtures in which the 2-monosubstituted kinetic products 37b,d predominate over the 2,3-disubstituted thermodynamic products 21c,e by a factor of 4:1 to 5:1. These results are opposite to those observed under the usual basic or acidic Friedländer reactions with methyl-n-alkylketones, where the thermodynamic products are usually strongly favored. The unusual kinetic:thermodynamic product ratios observed with 38a,b are ascribed to the generation and rapid cyclization of mixtures of the Schiff bases 35 and 36, in which the kinetic isomer 35 is highly predominant. Key words: mechanism, Friedländer synthesis, quinolines, intramolecular aldol reactions, Schiff bases, tetrahydroquinolines, high kinetic:thermodynamic product ratios.

APA, Harvard, Vancouver, ISO, and other styles

45

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.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

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 (March 31, 2018): 44–48. http://dx.doi.org/10.5155/eurjchem.9.1.44-48.1679.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

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 (February 25, 2020): 959–64. http://dx.doi.org/10.14233/ajchem.2020.22542.

Full text

Abstract:

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 cyclization along with formylation give corresponding 2-chloro-3-formyl quinoline. The synthesized compounds were screened for in vitro antimalarial, anti-inflammatory, antioxiadant and antidiabetic activities. The structures of the synthesized compounds were characterized by infrared, 1H NMR and 13C NMR spectroscopy. Compounds 1f and 1h showed highest antimalarial activity even more than standard chloroquine diphosphate. Compound 1a showed excellent activity whereas 1c and 1d showed potent anti-inflammatory activity as compared to standard diclofenac. On the other hand, compounds 1a and 1g showed excellent antioxidant activity for 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical while compound 1a showed highest inhibition of nitic oxide free radical (NO•) and compound 1h showed highest inhibition for super oxide radical (SOR) as well as highest antidiabetic activity as compared to standard acarbose. All quinolne based chalcones were synthesized in good yields and showed potential biological activities hence they may be helpful for the designing of new drugs.

APA, Harvard, Vancouver, ISO, and other styles

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 (November 1, 2008): 295–302. http://dx.doi.org/10.2174/157019308786242197.

Full text

APA, Harvard, Vancouver, ISO, and other styles

49

Rowlands, Gareth J., Rebecca J. Severinsen, Jenna K. Buchanan, Karl J. Shaffer, Heather T. Jameson, Nishani Thennakoon, Ivo Leito, et al. "Synthesis and Basicity Studies of Quinolino[7,8-h]quinoline Derivatives." Journal of Organic Chemistry 85, no. 17 (July 30, 2020): 11297–308. http://dx.doi.org/10.1021/acs.joc.0c01428.

Full text

APA, Harvard, Vancouver, ISO, and other styles

50

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.

Full text

Abstract:

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.

APA, Harvard, Vancouver, ISO, and other styles

We offer discounts on all premium plans for authors whose works are included in thematic literature selections. Contact us to get a unique promo code!