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Search for "quinolines" in Full Text gives 88 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis of pyrrolo[1,2-a]quinolines by formal 1,3-dipolar cycloaddition reactions of quinolinium salts

  • Anthony Choi,
  • Rebecca M. Morley and
  • Iain Coldham

Beilstein J. Org. Chem. 2019, 15, 1480–1484, doi:10.3762/bjoc.15.149

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  • Anthony Choi Rebecca M. Morley Iain Coldham Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, S3 7HF, UK 10.3762/bjoc.15.149 Abstract Quinolinium salts, Q+-CH2-CO2Me Br− and Q+-CH2-CONMe2 Br− (where Q = quinoline), were prepared from quinolines. Deprotonation of these salts
  • with electron-poor alkenes occurs through a stepwise conjugate addition–cyclization process [23]. We were interested in the related quinolinium ylides that, on (formal) cycloaddition would provide pyrrolo[1,2-a]quinolines as products. These are tricyclic compounds consisting of a pyrrole ring fused
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Published 03 Jul 2019

Quinolines from the cyclocondensation of isatoic anhydride with ethyl acetoacetate: preparation of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate and derivatives

  • Nicholas G. Jentsch,
  • Jared D. Hume,
  • Emily B. Crull,
  • Samer M. Beauti,
  • Amy H. Pham,
  • Julie A. Pigza,
  • Jacques J. Kessl and
  • Matthew G. Donahue

Beilstein J. Org. Chem. 2018, 14, 2529–2536, doi:10.3762/bjoc.14.229

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  • electrophiles are reacted with the sodium enolate of ethyl acetoacetate, generated from sodium hydroxide, in warm N,N-dimethylacetamide resulting in the formation of substituted quinolines. A degradation–build-up strategy of the ethyl ester at the 3-position allowed for the construction of the α-hydroxyacetic
  • ], quinolines are only present in approximately 2% of FDA approved prescription pharmaceuticals [2]. Recently, 2,3,4-trisubstituted arylquinolines such as BI 224436 1 [3][4] and 2 [5][6] have been shown to exhibit inhibitory activity against HIV-1 integrase that is essential for viral replication through
  • regioselectivity issues and practical challenges associated with the aniline cyclocondensation (7→8), along with the scarcity of commercially available highly substituted quinolines, we sought to employ an entirely different tactic by utilizing 2H-3,1-benzoxazine-2,4(1H)-dione (isatoic anhydride) chemistry [16][17
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Published 28 Sep 2018

Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal

  • Antonio Arcadi,
  • Sandro Cacchi,
  • Giancarlo Fabrizi,
  • Francesca Ghirga,
  • Antonella Goggiamani,
  • Antonia Iazzetti and
  • Fabio Marinelli

Beilstein J. Org. Chem. 2018, 14, 2411–2417, doi:10.3762/bjoc.14.218

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  • -catalyzed reaction of 15a with aldehydes as electrophiles resulted in the divergent formation of 11H-indolo[3,2-c]quinolines 17 (Scheme 5b) [32] through functionalization of C-3 position of the indole ring instead of N-1. The sequential reaction shown in Scheme 5, path a, probably occurs through cyclization
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Published 14 Sep 2018

Hydroarylations by cobalt-catalyzed C–H activation

  • Rajagopal Santhoshkumar and
  • Chien-Hong Cheng

Beilstein J. Org. Chem. 2018, 14, 2266–2288, doi:10.3762/bjoc.14.202

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  • styrenes, while alkylalkenes resulted in linear-selective products 35b. Similarly, quinolines 34a also underwent hydroarylation reaction with styrene to give C4-selective alkylated products 36 in good regioselectivity (Scheme 24b) [76]. 2.2 Co(III)-catalyzed hydroarylation of alkenes In 2013, Kanai
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Published 29 Aug 2018

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

  • Michael K. Bogdos,
  • Emmanuel Pinard and
  • John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

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  • nicotinamides to highly functionalised quinolines, such as the antimalarial drug quinine. The ability of this protocol to tolerate such highly functionalised molecules, with such a variety of functional groups present, really justifies the claims of the authors that this protocol is ideal for LSF in drug
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Published 03 Aug 2018

Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines)

  • Michał Nowacki and
  • Krzysztof Wojciechowski

Beilstein J. Org. Chem. 2018, 14, 194–202, doi:10.3762/bjoc.14.14

Graphical Abstract
  • as anticancer agents [1][6][7] (Figure 1). Synthetic strategies towards indolo[3,2-b]quinolines have been reviewed [8]. These methodologies usually employ multistep procedures. Selected starting materials applicable to the synthesis of indolo[3,2-b]quinolines are presented in Scheme 1. Bis(2
  • pharmaceutical applications [19]. During our studies on the reactions of nitroarenes with nucleophiles [20][21][22][23], particularly carbanions, we were interested in a direct transformation of the formed σH-adducts into heterocyclic systems – indoles [21][23] and quinolines [21][22]. Quinolines were formed
  • heteroanalogues of benzyl carbanions to synthesise 11-substituted norcryptotackieine derivatives (indolo[2,3-b]quinolines) [26], benzothieno[2,3-b]quinolines [27], and other tetra- and pentacyclic polyazaarenes containing the quinoline system [28]. We elaborated two general variations of this methodology. In the
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Published 23 Jan 2018

CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF3SO2Na

  • Hélène Guyon,
  • Hélène Chachignon and
  • Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2764–2799, doi:10.3762/bjoc.13.272

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  • good oxidant for this reaction and allowed to carry out the trifluoromethylation exclusively at the α-position of the carbonyl group in the pyranone ring. The substrate scope was large and included 17 coumarins, 2 quinolines and 3 pyrimidinones. With coumarins bearing electron-donating groups on the
  • five cycles of this heterogeneous trifluoromethylation. In 2017, Lu, Weng and co-workers reported a protocol for the para-selective trifluoromethylation of naphthylamide 70, instead of the previously studied quinolines, with CF3SO2Na, tert-butyl hydroperoxide and Cu(OAc)2·H2O as oxidant (Scheme 46) [69
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Published 19 Dec 2017

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

  • Martina Tireli,
  • Silvija Maračić,
  • Stipe Lukin,
  • Marina Juribašić Kulcsár,
  • Dijana Žilić,
  • Mario Cetina,
  • Ivan Halasz,
  • Silvana Raić-Malić and
  • Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

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  • reactions using Cu(II), Cu(I) and Cu(0) catalysts have been successfully implemented to provide novel 6-phenyl-2-(trifluoromethyl)quinolines with a phenyl-1,2,3-triazole moiety at O-4 of the quinoline core. Milling procedures proved to be significantly more efficient than the corresponding solution
  • click reaction to provide the target 6-phenyl-2-(trifluoromethyl)quinolines containing p-halogen-substituted and non-substituted phenyl-1,2,3-triazole unit attached at the O-4 position of the quinoline fragment. All triazole products have almost identical conformations in the solid state, with no
  • gray. c) Capped-stick representation of 5, showing the dimer formed by C–H∙∙∙N hydrogen bond (orange stippled lines). Synthetic procedures for preparation of p-halogen-substituted and non-substituted phenyl-1,2,3-triazole 6-phenyl-2-(trifluoromethyl)quinolines. Reaction conditions and yields for the
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Published 06 Nov 2017

Solvent-free and room temperature synthesis of 3-arylquinolines from different anilines and styrene oxide in the presence of Al2O3/MeSO3H

  • Hashem Sharghi,
  • Mahdi Aberi,
  • Mohsen Khataminejad and
  • Pezhman Shiri

Beilstein J. Org. Chem. 2017, 13, 1977–1981, doi:10.3762/bjoc.13.193

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  • optimized conditions for the synthesis of quinolines, the reaction of 3,4-dimethylaniline (1, 1.0 mmol) and styrene oxide (2, 2.0 mmol) in an open atmosphere was chosen as a model reaction (Table 1). Control experiments showed that in the absence of Al2O3 and MeSO3H, no quinoline 3a was observed (Table 1
  • with styrene oxide to form the desired products (Table 2). In continuation of our study, aliphatic epoxides were also checked; unfortunately, they were not applicable for the preparation of quinolines. All novel and known compounds were characterized by their melting points, IR, 1H NMR, 13C NMR and
  • . Column chromatography was carried out on short columns of silica gel 60 (70–230 mesh) in glass columns. General procedure for the synthesis of quinolines in the presence of Al2O3/MeSO3H Aniline (1.0 mmol) and styrene oxide (2.0 mmol) were added to a mixture of MeSO3H (0.3 mL) and Al2O3 (0.1 g). The
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Published 20 Sep 2017

Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

  • Santanu Hati,
  • Ulrike Holzgrabe and
  • Subhabrata Sen

Beilstein J. Org. Chem. 2017, 13, 1670–1692, doi:10.3762/bjoc.13.162

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  • mechanisms (radical and metal-catalyzed) of the transformation. Ferric chloride-catalyzed, TBHP-oxidized synthesis of substituted quinazolinones and arylquinazolines. Iridium-catalyzed oxidative dehydrogenation of quinolines. Microwave-assisted synthesis of β-carboline with a catalytic amount of Pd/C in
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Published 15 Aug 2017

Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides

  • Ryota Miyaji,
  • Yuuki Wada,
  • Akira Matsumoto,
  • Keisuke Asano and
  • Seijiro Matsubara

Beilstein J. Org. Chem. 2017, 13, 1518–1523, doi:10.3762/bjoc.13.151

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  • have recently demonstrated that bifunctional organocatalysts can also be applied to the asymmetric synthesis of axially chiral compounds (biaryls bearing isoquinoline N-oxides or quinolines and phenolic moieties) by translating a specific conformation, recognized by bifunctional organocatalysts, into
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Published 02 Aug 2017

Effect of the ortho-hydroxy group of salicylaldehyde in the A3 coupling reaction: A metal-catalyst-free synthesis of propargylamine

  • Sujit Ghosh,
  • Kinkar Biswas,
  • Suchandra Bhattacharya,
  • Pranab Ghosh and
  • Basudeb Basu

Beilstein J. Org. Chem. 2017, 13, 552–557, doi:10.3762/bjoc.13.53

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  • ], 3-aminobenzofurans [12], aminoindolizines [13], 2-aminoimidazoles [14], oxazolidinones [15], and quinolines [16] (Scheme 1). Because of diverse applications of propargylamine, several methods are developed among which the three–component reaction of aldehyde, amine and terminal alkyne, commonly
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Published 16 Mar 2017

New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation

  • Pavel Nagorny and
  • Zhankui Sun

Beilstein J. Org. Chem. 2016, 12, 2834–2848, doi:10.3762/bjoc.12.283

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  • the titration of L4 with TBAC [37]. Catalysts L3 and L4 were successfully applied to the asymmetric dearomatization of electron-deficient N-heteroarenes (Scheme 3). Various nitrogen-containing heterocycles such as pyridines [36], quinolines [38], isoquinolines [38], etc. were reacted with TrocCl to
  • 2008 the Bolm group explored the use of halogen bond donors in organocatalysis. They discovered that perfluorinated alkyl halides could activate 2-substituted quinolines toward reduction by Hantzsch ester (Scheme 15) [81]. These studies explored various C6 to C10 perfluorinated bromides and iodides. It
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Published 23 Dec 2016

Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives

  • Larisa Yu. Gurskaya,
  • Diana S. Belyanskaya,
  • Dmitry S. Ryabukhin,
  • Denis I. Nilov,
  • Irina A. Boyarskaya and
  • Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2016, 12, 950–956, doi:10.3762/bjoc.12.93

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  • very important class of heterocycles, which are used in chemistry, biology, medicine, and materials science. For instance, see a series of recent reviews on anti-malaria drugs containing a quinoline motif in the structure [1][2][3]. The synthesis of quinolines is an important task of organic chemistry
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Published 11 May 2016

Synthesis of 2,1-benzisoxazole-3(1H)-ones by base-mediated photochemical N–O bond-forming cyclization of 2-azidobenzoic acids

  • Daria Yu. Dzhons and
  • Andrei V. Budruev

Beilstein J. Org. Chem. 2016, 12, 874–881, doi:10.3762/bjoc.12.86

Graphical Abstract
  • ], quinolines [9][10][11][12][13] and quinazolines [14][15][16]. Therefore, the search for new methods leading to 2,1-benzisoxazoles is of great interest. For the preparative synthesis of 2,1-benzisoxazoles, in addition to the traditional method based on the reductive heterocyclization of ortho-substituted
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Published 04 May 2016

Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen

  • Hans Sterckx,
  • Johan De Houwer,
  • Carl Mensch,
  • Wouter Herrebout,
  • Kourosch Abbaspour Tehrani and
  • Bert U. W. Maes

Beilstein J. Org. Chem. 2016, 12, 144–153, doi:10.3762/bjoc.12.16

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  • , benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial
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Published 27 Jan 2016

Enantioselective additions of copper acetylides to cyclic iminium and oxocarbenium ions

  • Jixin Liu,
  • Srimoyee Dasgupta and
  • Mary P. Watson

Beilstein J. Org. Chem. 2015, 11, 2696–2706, doi:10.3762/bjoc.11.290

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  • intermediates have been achieved. α-Chiral piperidines, quinolines, isoquinolines, and benzopyrans are accessible via these reactions. The utility of these alkyne-substituted products has been demonstrated via elaboration to biologically active natural products. As evidenced by the most recent reports
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Published 22 Dec 2015

Synthesis of a tricyclic lactam via Beckmann rearrangement and ring-rearrangement metathesis as key steps

  • Sambasivarao Kotha,
  • Ongolu Ravikumar and
  • Jadab Majhi

Beilstein J. Org. Chem. 2015, 11, 1503–1508, doi:10.3762/bjoc.11.163

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  • -caprolactam from cyclohexanone oxime involving the BR. The activation energy for the BR is almost the same as that of the nucleophilic substitution at sp2 nitrogen. To synthesize various aza-arenes and cyclic imines, such as quinolines, aza-spiro compounds and dihydropyrroles, the intramolecular SN2-type
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Published 27 Aug 2015

Tandem Cu-catalyzed ketenimine formation and intramolecular nucleophile capture: Synthesis of 1,2-dihydro-2-iminoquinolines from 1-(o-acetamidophenyl)propargyl alcohols

  • Gadi Ranjith Kumar,
  • Yalla Kiran Kumar,
  • Ruchir Kant and
  • Maddi Sridhar Reddy

Beilstein J. Org. Chem. 2014, 10, 1255–1260, doi:10.3762/bjoc.10.125

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  • classical Chichibabin reaction [47], there has been considerable interest shown for the synthesis of these compounds with varying substitution patterns [48][49][50][51][52][53][54][55][56][57][58][59][60][61][62][63][64]. Most of the methods used presynthesized quinolines for the 2-amination via either
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Published 28 May 2014

Aza-Diels–Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome

  • Amitabh Jha,
  • Ting-Yi Chou,
  • Zainab ALJaroudi,
  • Bobby D. Ellis and
  • T. Stanley Cameron

Beilstein J. Org. Chem. 2014, 10, 848–857, doi:10.3762/bjoc.10.81

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  • the N-aryl group undergo intramolecular electrophilic addition to the alkene yielding isoindolo[2,1-a]quinolines under acidic conditions [18]. Isoindolo[2,1-a]quinolone cores have also been prepared via an aldol-type intramolecular cyclization reaction of N-(2-acetylaryl)phthalimide under anhydrous
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Published 14 Apr 2014

Dimerisation, rhodium complex formation and rearrangements of N-heterocyclic carbenes of indazoles

  • Zong Guan,
  • Jan C. Namyslo,
  • Martin H. H. Drafz,
  • Martin Nieger and
  • Andreas Schmidt

Beilstein J. Org. Chem. 2014, 10, 832–840, doi:10.3762/bjoc.10.79

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  • available by copper-catalyzed aryl couplings or Buchwald–Hartwig reactions [22]. Pyrazol-3-ylidenes rearrange similarly to quinolines [17]. We report here on two unexpected rearrangements of indazol-3-ylidene, and trapping reactions of the N-heterocyclic carbene with rhodium. Results and Discussion On
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Published 10 Apr 2014

Use of activated enol ethers in the synthesis of pyrazoles: reactions with hydrazine and a study of pyrazole tautomerism

  • Denisa Tarabová,
  • Stanislava Šoralová,
  • Martin Breza,
  • Marek Fronc,
  • Wolfgang Holzer and
  • Viktor Milata

Beilstein J. Org. Chem. 2014, 10, 752–760, doi:10.3762/bjoc.10.70

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  • trifunctional electrophiles and are useful building blocks for the introduction of a three carbon fragment into the resulting molecule. Thus, the reaction of enol ethers with hydrazines produces pyrazoles, with amidines pyrimidines, with hydroxylamine isoxazoles, and with anilines quinolines/ones are formed [2
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Published 01 Apr 2014

Copper–phenanthroline catalysts for regioselective synthesis of pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and of pyrrolo[1,2-a]phenanthrolines under mild conditions

  • Rupankar Paira,
  • Tarique Anwar,
  • Maitreyee Banerjee,
  • Yogesh P. Bharitkar,
  • Shyamal Mondal,
  • Sandip Kundu,
  • Abhijit Hazra,
  • Prakas R. Maulik and
  • Nirup B. Mondal

Beilstein J. Org. Chem. 2014, 10, 692–700, doi:10.3762/bjoc.10.62

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  • , antifungal, antitumor and anti-HIV candidates [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15]. We have also been pursuing the cycloaddition methodology for several years and established some synthetic routes towards indolizines, pyrrolo[1,2-a]quinolines/isoquinolines, oxazadicyclopenta[a,h]naphthalenes
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Published 20 Mar 2014

New syntheses of 5,6- and 7,8-diaminoquinolines

  • Maroš Bella and
  • Viktor Milata

Beilstein J. Org. Chem. 2013, 9, 2669–2674, doi:10.3762/bjoc.9.302

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  • -substituted quinolines, making their separation necessary. To avoid these drawbacks, the readily available angularly annelated selenadiazoloquinolones, prepared as detailed in our previous papers [13][14], were employed as the precursors of o-diaminoquinoline derivatives. The preparation and application of
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Published 27 Nov 2013

Recent advances in transition metal-catalyzed Csp2-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation

  • Grégory Landelle,
  • Armen Panossian,
  • Sergiy Pazenok,
  • Jean-Pierre Vors and
  • Frédéric R. Leroux

Beilstein J. Org. Chem. 2013, 9, 2476–2536, doi:10.3762/bjoc.9.287

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  • [114] as well as of various arenes and heteroarenes (pyridines, pyrimidines, pyrazines, quinolines, pyrroles, thiophenes, furans, pyrazoles, imidazoles, thiazoles, oxazoles, thiadiazoles, triazoles) [115]. The yields were low to excellent, depending on the substrate (Scheme 12 and Figure 20). Iron(II
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Published 15 Nov 2013
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