Efficient and selective synthesis of quinoline derivatives. Quinolines were first synthesized in 1879, and since then a multitude of. Solventfree synthesis of quinoline derivatives via the friedlander reaction using 1,3disulfonic acid imidazolium hydrogen sulfate as an efficient and recyclable. Quinoline appears as a colorless liquid with a peculiar odor. In an attempt to find new bioactive antimicrobial molecules, a series of quinoline3carbonitrile and 2chloroquinoline derivatives were synthesized by multistep reactions. A combinatorial synthesis of pyrrolo3,2fquinoline and pyrrolo3,2aacridine derivatives is described as a threecomponent reaction of aromatic aldehyde, 1hindol5amine, and 1,3dicarbonyl compounds under catalystfree conditions. A mild, efficient, and general method for the synthesis of benzofquinoline and benzoaphenanthridine derivatives by a three. It is named after the czech chemist zdenko hans skraup 18501910. The reaction was carried out in solvent free conditions under microwave. Friedlander prepared quinoline in 1882 by the condensation of o aminobenzaldehyde with acetaldehyde in the presence of sodium hydroxide. Pdf quinoline or 1azanaphthalene is a weak tertiary base. Quinoline is a heterocyclic scaffold of paramount importance to human race.
Pdf synthesis and cytotoxicity of new quinoline derivatives. Synthesis of quinoline derivatives via cucatalyzed cascade. An efficient green method for the synthesis of oxazino quinoline 2amine derivatives, oxazino quinoline derivatives and chromeno oxazin5one derivatives have been synthesized through cyclization of aromatic aldehyde, ammonium acetate, substituted amides and 8hydroxy quinoline or 4hydroxy coumarin by onepot condensation method is described. Their antibacterial 1 activities against five gramnegative escherichia coli, salmonella. As a result, the synthesis of quinoline core and its derivatives have been an attractive goal for the synthetic organic chemist. Quinoline is a heterocyclic aromatic organic compound with the chemical formula c9h7n.
The reaction could be carried out under solventfree condition and gave low yield. It ignites readily, burning with a smoky flame characteristic of aromatic compounds, the amine is nearly planar owing to conjugation of the lone pair with the aryl substituent. Quinolines have antiseptic, antipyretic, and antiperiodic properties and are used as antimalarials and for preparing other antimalarial drugs. Pdf microwave enhanced solventfree synthesis of a library. Synthesis and biological activity investigation of some. For the synthesis of quinolines, various methods have been reported including the skraup, conradlimpachknorr, pfitzinger, friedlander, and combes. Intheattemptstosynthesizecompoundswith structuresrelatedtoquinine,itwasfirstnecessarytogeta compoundfromwhichtostartthesynthesis. Advances in the syntheses of quinoline and quinoline. Organometallic derivatives of quinoline and isoquinoline. Microwave enhanced solventfree synthesis of a library of quinoline derivatives. The 1,3dicarbonyl compounds include 5,5dimethylcyclohexane1,3dione, cyclopentane1,3dione, and 2hindene1,3dione. Pharmacokinetic pk studies of compound 7a the most potent pde5i of our quinoline analogs were also performed.
New quinoline 2one derivatives were synthesized by reaction of 4,7dimethyl coumarin i with nitric acid in the presence of concentrated sulfuric acid to afford 4,7dimethyl6nitrocoumarin ii and 4,7dimethyl8nitrocoumarin iii. Synthesis and biological potentials of quinoline analogues. Inspired by the diversity of the synthetic pathways, solvent free, microwave. In this study we report the synthesis and pde activity of a series of quinoline derivatives. Selective synthesis of substituted aminoquinoline derivatives by ch activation and fluorescence evaluation of their lipophilicityresponsive properties. Organometallic derivatives of quinoline and isoquinoline theodore stephen soddy iowa state college follow this and additional works at. Several quinoline derivatives isolated from natural resources or prepared synthetically are significant with respect to medicinal chemistry and biomedical use. Introduction activity against pseudomonas vulgaris, staphylococcus aureus, aspergillus niger and pseudomonas chrysogenum.
Synthesis of quinoline derivatives by a doebnervon miller. Quinoline derivatives are prevalent in a variety of pharmacologically active synthetic and natural compounds. The parent compound 18 and new quinoline derivatives 1926 were prepared from the corresponding quinoline hydrazones and substituted carboxylic acids using edc. Different groups, such as methyl, fluoro, chloro, bromo, methoxy, and ester linked on benzene rings, are tolerated under. Therefore, many researchers have synthesized these compounds as target structures and evaluated their biological activities. Abdelbaset faculty of pharmacy, department of pharmaceutical organic chemistry, al. New quinoline2one derivatives were synthesized by reaction of 4,7dimethyl coumarin i with nitric acid in the presence of concentrated sulfuric acid to afford 4,7dimethyl6nitrocoumarin ii and 4,7dimethyl8nitrocoumarin iii. Microwave enhanced solvent free synthesis of a library of quinoline derivatives. Solventfree synthesis of quinoline derivatives via the friedlander.
With regard to anticancer properties, in vitro cytotoxicities against three human cancer cell lines a. It is a mancude organic heterobicyclic parent, a member of quinolines, an azaarene and an orthofused heteroarene. Derivatives of quinoline moiety plays very important role in the development of various types of newer drugs and it can be used as lead compounds for future investigation in the field of drug discovery process. Fiorito j1, saeed f, zhang h, staniszewski a, feng y, francis yi, rao s, thakkar dm, deng sx, landry dw, arancio o. Quinoline and quinolinone ring systems are present in a diverse array of natural products such as tecleabine, tecleoxime, pancratistatin, plakinidine and quinine. Discovery of a potent and selective phosphodiesterase 5 inhibitor for the treatment of alzheimers disease jole fiorito, a faisal saeed, a hong zhang, a agnieszka staniszewski, a yan feng, a yitshak i. The design and synthesis of the titled compounds were carried out with two objectives. In the absence of the alkali metal acetate cyclization takes place in a different direction. The benzene ring contains six carbon atoms, while the pyridine ring contains five carbon atoms and a nitrogen atom. Synthesis of benzo f quinoline and its derivatives. The new ligands were characterized by elemental analyses, ftir and hnmr.
Reduction of nitrobenzene using ammonium chloride and zinc dust in hot water afforded phenyl hydroxylamine 5. Sulfuric acid,glycerol and mild oxidising agent are heated together 16. Synthesis of some quinoline21hone and 1, 2, 4 triazolo 4, 3 a quinoline derivatives as potent anticonvulsants liping guan,a, b qinghao jin,b guanrong tian,d kyuyun chai,c and zheshan quan, a, b, a key laboratory of organism functional factors of the changbai mountainyanbian university. A straightforward synthesis of oxazino2,3,4ijquinoline. Anilidoquinoline 65 derivatives synthesized by ghosh et al. Aug 05, 20 a combinatorial synthesis of pyrrolo3,2f quinoline and pyrrolo3,2aacridine derivatives is described as a threecomponent reaction of aromatic aldehyde, 1hindol5amine, and 1,3dicarbonyl compounds under catalyst free conditions. The compound ii was treated with hydrazine hydrate 80% in pyridine to give n amino4,7dimethy 6nitroquinoline2one iv. A mechanism for this reaction has been proposed as taking place. Several alkaloid quinoline compounds found in plants are important medicines. The structure of the synthesized products was elucidated by a. The electronic spectra of linear benzog quinoline, its 4substituted derivatives, and some hydrogenated derivatives are examined and discussed. There are multiple ways to synthesize quinoline, one of which is the combes quinoline synthesis. Combinatorial synthesis of pyrrolo3,2fquinoline and.
However, the friedlander condensation is still considered as a popular method for the synthesis of quinoline derivatives 914. Design, synthesis, and dual evaluation of quinoline and. Aged samples, if exposed to light,become yellow and later brown. Itis a colorless hygroscopic liquid with a strong odor. Quinoline is the simplest member of the quinoline class of compounds, comprising a benzene ring ortho fused to c2 and c3 of a pyridine ring. This sequential transformation was efficient, conducted under metalfree and mild. Design, synthesis and antimicrobial evaluation of some. An efficient method for the synthesis of benzofquinoline. A possible reaction mechanism for the formation of the product is proposed based on further experimental results. Reagents and conditions a br 2 3 equiv, chcl 3, dark, rt, 2 d.
Molecules free fulltext design, synthesis, and in vitro. Pdf nano sno 2 catalyzes the twocomponent reaction of. Design, synthesis, and antifungal evaluation of novel. Synthesis and antimicrobial activity of novel glyoximes. The new compounds were characterized by ir, 1hnmr and mass spectra. Indispensability of quinoline moiety in the field of. Proficient procedure for preparation of quinoline derivatives. Us2211538a us239505a us23950538a us2211538a us 2211538 a us2211538 a us 2211538a us 239505 a us239505 a us 239505a us 23950538 a us23950538 a us 23950538a us 2211538 a us2211538 a us 2211538a authority us united states prior art keywords acid quinoline phenyl synthesis sulfonic prior art date 19381108 legal status the legal status is an assumption and is not. Further, we investigated the effect of 7a on synaptic dysfunction and cognitive abnormalities in two mouse models of ad, a transgenic model the appps1 mouse and a nontransgenic model in. The electronic spectra of linear benzogquinoline, its 4substituted derivatives, and some hydrogenated derivatives are examined and discussed. Treatment of some aminoquinolines with antichloroglyoxime gave three new compounds as a ligand.
Antimicrobial screening of title compounds 324 was carried out against grampositive and gram negative bacteria and fungi using agar diffusion technique. Quinoline and its fused heterocyclic derivatives tested with diverse pharmacological activity functional groups constitute an important class of compounds for new drug development. Quinoline derivatives are essential for drug development and have diverse applications in many fields including analytical, biological, and inorganic chemistry. The synthesis of quinoline derivatives has been prevalent in biomedical studies due to the efficiency of the synthetic methods as well as the relative lowcost production of these compounds, which can also be produced in large scales. Synthesis of benzogquinoline derivatives springerlink. Synthesis of dihydropyrazoles via ligandfree pdcatalyzed alkene. An efficient green method for the synthesis of oxazino quinoline2amine derivatives, oxazino quinoline derivatives and chromeno oxazin5one derivatives have been synthesized through cyclization of aromatic aldehyde, ammonium acetate, substituted amides and 8hydroxyquinoline or 4hydroxy coumarin by onepot condensation method is described. Various quinoline derivatives are obtained in satisfactory to excellent yields. The utility of quinoline derivatives in the areas of medicine, food, catalyst, dye, materials, refineries and electronics is well established. Request pdf on jan 14, 2003, axelle arrault and others published a straightforward synthesis of oxazino2,3,4ij quinoline derivatives from 8hydroxyquinolines find, read and cite all the. Herein, we design and synthesize an array of benzofuro3,2cquinolines starting from. These include antiinflammatory and antitumor agents, the antimalarial drugs quinine and chloroquine, and organic lightemitting diodes. In the archetypal skraup reaction, aniline is heated with sulfuric acid, glycerol, and an oxidizing agent such as nitrobenzene to yield quinoline.
Quinoline definition of quinoline by medical dictionary. The results showed that compounds 3e and 3f series exhibited significant fungicidal activities. The parent compound 18 and new quinoline derivatives 1926 were prepared from the corresponding quinoline hydrazones and substituted carboxylic acids using edcmediated peptide. Quinolines heterocyclic building blocks sigmaaldrich. Pdf different heterocyclic analogues were evaluated for their. The reaction proceeds via dehydration of glycerol to acrolein. Novel quinoline derivatives carrying nitronesoximes nitric. Pdf synthesis of quinoline derivatives from the reaction of. Synthesis of quinoline derivatives download pdf info. Synthesis of derivatives of 2 phenyl quinoline 4 carboxylic acid.
Novel quinoline derivatives carrying nitronesoximes nitric oxide donors. The simplest member of the quinoline family is quinoline itself, a. Synthesis of novel cyano quinoline derivatives sciencedirect. Also, these compounds have acquired attention of synthetic and biological chemists due to their vital role in many pharmacological activities such as antiinflammatory, anticonvulsant, antibacterial, antitubercular. Synthesis of quinoline derivatives using ketene dithioacetals synthesis of quinoline derivatives using ketene dithioacetals tominaga, yoshinori. Novel quinoline derivatives carrying nitronesoximes. The synthesis and in vitro antimicrobial evaluation of several quinoline derivatives of glyoximes were described. Inspired by quinine and its analogues, we designed, synthesized, and evaluated two series of quinoline small molecular compounds a and 2a and six series of quinoline derivatives 3a f for their antifungal activities. A possible reaction mechanism for the formation of the product is proposed based on further. An environmentally friendly and highly efficient procedure gives 2,4disubstituted quinoline derivatives by a simple alkynylationcyclization reaction of 2aminoaryl ketones with phenylacetylenes in the presence of indiumiii trifluoromethanesulfonate inotf 3 under microwave irradiation and solvent free conditions. The skraup synthesis is a chemical reaction used to synthesize quinolines. An environmentally friendly and highly efficient procedure gives 2,4disubstituted quinoline derivatives by a simple alkynylationcyclization reaction of 2aminoaryl ketones with phenylacetylenes in the presence of indiumiii trifluoromethanesulfonate inotf 3 under microwave irradiation and solventfree conditions. Bronsted acidcatalyzed metal and solventfree quinoline.
Quinoline is only slightly soluble in cold water but dissolvesreadily in hot water and most organic solvents. A series of novel quinoline and quinolinium iodide derivatives were designed and synthesized to discover potential anticancer and antibacterial agents. Thus, we have opened up two effective and selective methods for the synthesis of cyanide 8, which is a potential precursor for other quinoline derivatives due to the bromine substituents. Part of theorganic chemistry commons this dissertation is brought to you for free and open access by the iowa state university capstones, theses and dissertations at iowa state.
Quinoline can be prepared by heating a mixture of aniline, glycerol, and sulfuric acid 1 alone or with an oxidizing agent like nitrobenzene, 2 arsenic acid, 3 ferric oxide, 4 and vanadic acid. Nov 09, 2012 quinoline is a heterocyclic aromatic organic compound with the chemical formula c9h7n. Synthesis, classical and electrochemical evaluation of antioxidant, antiinflammatory, antimicrobial activities and the dna bsa binding author links open overlay panel khaoula douadi a salah chafaa a tahar douadi a mousa alnoaimi b ilhem kaabi a. Design, synthesis, and in vitro evaluation of benzofuro3,2cquinoline derivatives as potential antileukemia agents. Selective synthesis of substituted amino quinoline derivatives by ch activation and fluorescence evaluation of their lipophilicityresponsive properties. Quinoline, any of a class of organic compounds of the aromatic heterocyclic series characterized by a doublering structure composed of a benzene and a pyridine ring fused at two adjacent carbon atoms. Bronsted acidcatalyzed cyclization reactions of nalkyl anilines with alkynes or alkenes in the presence of oxygen gas as an oxidant under metal and solventfree conditions are described. The synthesis, in silico studies, antiprotozoal and cytotoxic activities of eleven quinoline. The quinoline ring system is one of the most ubiquitous heterocycles in the fields of medicinal and industrial chemistry, forming the scaffold for compounds of great significance. Apr 15, 2020 quinoline, any of a class of organic compounds of the aromatic heterocyclic series characterized by a doublering structure composed of a benzene and a pyridine ring fused at two adjacent carbon atoms. Friedlander reaction, quinoline derivatives, heteropoly compound, supported catalysts, solventfree condition. Recent advances in metalfree quinoline synthesis mdpi. Our aim is to produce the quinoline derivatives with the more. Synthesis of quinoline derivatives by a doebnervon miller reaction.
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