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Search for "naphthoquinone" in Full Text gives 34 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis of polycyclic aromatic quinones by continuous flow electrochemical oxidation: anodic methoxylation of polycyclic aromatic phenols (PAPs)

  • Hiwot M. Tiruye,
  • Solon Economopoulos and
  • Kåre B. Jørgensen

Beilstein J. Org. Chem. 2024, 20, 1746–1757, doi:10.3762/bjoc.20.153

Graphical Abstract
  • properties make them privileged structures in medicinal chemistry [2]. Benzoquinone and naphthoquinone can exist as ortho-quinone and para-quinone, with the latter considered more stable [5]. Additionally, p- and o-quinones are formed in metabolism of drugs [6] as well as polycyclic aromatic hydrocarbons
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Published 24 Jul 2024

Methodology for awakening the potential secondary metabolic capacity in actinomycetes

  • Shun Saito and
  • Midori A. Arai

Beilstein J. Org. Chem. 2024, 20, 753–766, doi:10.3762/bjoc.20.69

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  • , ytterbium (Yb), but not in the presence of other metals. Structural analyses revealed that this pigment is a type of naphthoquinone similar to nanaomycin (24) [64]. Furthermore, Tanaka et al. showed that low concentrations of the rare earth elements scandium (Sc) and/or lanthanum (La) markedly activate (2.5
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Published 10 Apr 2024

Copper-catalyzed N-arylation of amines with aryliodonium ylides in water

  • Kasturi U. Nabar,
  • Bhalchandra M. Bhanage and
  • Sudam G. Dawande

Beilstein J. Org. Chem. 2023, 19, 1008–1014, doi:10.3762/bjoc.19.76

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  • -arylation of amines using iodonium ylides obtained from 2-hydroxy-1,4-naphthoquinone in the presence of a Cu(II) catalyst in dichloromethane as a solvent (Scheme 1b) [41]. Albeit useful, this protocol suffers drawbacks such as low yields, formation of byproducts, limited substrate study, and the use of
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Published 04 Jul 2023

Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

  • Elena R. Lopat’eva,
  • Igor B. Krylov,
  • Dmitry A. Lapshin and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2022, 18, 1672–1695, doi:10.3762/bjoc.18.179

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  • biomimetic oxidation of benzyl alcohols was developed using o-naphthoquinone [129] (Scheme 28). The reaction shows regioselectivity toward benzylic alcohol oxidation. This process could be included in one-pot synthesis strategies. The key step of the reaction is a 1,5-hydrogen transfer (the suggested
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Perspective
Published 09 Dec 2022

Menadione: a platform and a target to valuable compounds synthesis

  • Acácio S. de Souza,
  • Ruan Carlos B. Ribeiro,
  • Dora C. S. Costa,
  • Fernanda P. Pauli,
  • David R. Pinho,
  • Matheus G. de Moraes,
  • Fernando de C. da Silva,
  • Luana da S. M. Forezi and
  • Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

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  • , Brazil 10.3762/bjoc.18.43 Abstract Naphthoquinones are important natural or synthetic compounds belonging to the general class of quinones. Many compounds in this class have become drugs that are on the pharmaceutical market for the treatment of various diseases. A special naphthoquinone derivative is
  • menadione, a synthetic naphthoquinone belonging to the vitamin K group. This compound can be synthesized by different methods and it has a broad range of biological and synthetic applications, which will be highlighted in this review. Keywords: cancer; chemical reactions; 2-methyl-1,4-naphthoquinone
  • interesting chemical properties and bioactivities, naphthoquinones have aroused great interest, mainly in the pharmaceutical field, where they have been widely used in the development of new and more efficient drugs [1][9]. The naphthoquinone menadione has attracted a lot of attention. Menadione or 2-methyl
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Published 11 Apr 2022

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

  • Ruan Carlos B. Ribeiro,
  • Patricia G. Ferreira,
  • Amanda de A. Borges,
  • Luana da S. M. Forezi,
  • Fernando de Carvalho da Silva and
  • Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

Graphical Abstract
  • against various microorganisms and pharmacological targets, including being used in the preparation of several drugs that are on the pharmaceutical market. Among these naphthoquinones, the series of compounds prepared from 1,2-naphthoquinone-4-sulfonic acid salts (β-NQS) stands out. In addition to being
  • catecholamines and other compounds, but they can also be ingested as exogenous products of air and water. The most common quinones, such as benzoquinone, naphthoquinone, anthraquinone, and phenanthrenequinone, can be formed by incomplete combustion or photooxidation of their respective polycyclic aromatic
  • electrons through a redox cycle promoted by the 1,2- or 1,4-naphthoquinone system. In this cycle, transient reactive oxygen (ROS) and nitrogen (RNS) species are formed as free radicals, peroxides, superoxide anions, radical anions, or dianions. These species generated inside cells accelerate hypoxia and
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Published 05 Jan 2022

Recent advances in the syntheses of anthracene derivatives

  • Giovanni S. Baviera and
  • Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

Graphical Abstract
  • -workers [77] provided better results. In a related approach, Estévez-Braun and co-workers synthesized dibenzo[a,h]anthracene-12,13-diones 188 from 2-hydroxy-1,4-naphthoquinone (186), β-naphthol (181), and aromatic aldehydes 187 through a multicomponent reaction that used InCl3 as catalyst under solvent
  • multicomponent reactions employing 2-hydroxy-1,4-naphthoquinone (186), β-naphthol (181), and aromatic aldehydes. Synthesis of substituted anthraquinones catalyzed by an AlCl3/MeSO3H system. Palladium(II)-catalyzed/visible light-mediated synthesis of anthraquinones. [4 + 2] Anionic annulation reaction for the
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Published 10 Aug 2021

A straightforward conversion of 1,4-quinones into polycyclic pyrazoles via [3 + 2]-cycloaddition with fluorinated nitrile imines

  • Greta Utecht-Jarzyńska,
  • Karolina Nagła,
  • Grzegorz Mlostoń,
  • Heinz Heimgartner,
  • Marcin Palusiak and
  • Marcin Jasiński

Beilstein J. Org. Chem. 2021, 17, 1509–1517, doi:10.3762/bjoc.17.108

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  • naphthoquinone-derived products and low-intensity bands in the visible region (≈400 nm) for the anthraquinone series. Keywords: [3 + 2]-cycloadditions; fluorinated compounds; fused pyrazoles; N-heterocycles; nitrile imines; 1,4-quinones; Introduction The 1,4-quinone scaffold belongs to the most important
  • exclusively [16]. Noteworthy, [3 + 2]-cycloadditions of nitrile imines to the C=O group of 1,4-quinones have not yet been reported. In a historical work by Rolf Huisgen et al., the first [3 + 2]-cycloadditions of some 1,4-quinones, e.g., 1,4-naphthoquinone (1a), with C,N-diphenyl nitrile imine (2) were
  • 1,4-naphthoquinone (1a) and 1,4-anthraquinone (1b), which were selected as model dipolarophiles. In addition, an important issue of the work was the examination of the chemoselectivity governing the formation of five-membered rings via competitive cycloaddition of the in-situ-generated 1,3-dipoles
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Published 28 Jun 2021

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

  • Shivani Gulati,
  • Stephy Elza John and
  • Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

Graphical Abstract
  • exploring the MC-MWA reactions Jiang and co-workers [41] designed a microwave facilitated regioselective four-component domino reaction employing naphthyl- or anthracenylamine 10, aldehydes 5 and 2-hydroxy-1,4-naphthoquinone (11) in acetic acid for the construction of dibenzo[a,h]acridine-12,13(7H,14H
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Published 19 Apr 2021

Recent developments in enantioselective photocatalysis

  • Callum Prentice,
  • James Morrisson,
  • Andrew D. Smith and
  • Eli Zysman-Colman

Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197

Graphical Abstract
  • naphthoquinones 216 to afford enantioenriched benzofuranones 217 (Scheme 33) [93]. They then expanded the scope of the naphthoquinone by coupling this reaction with a photocatalysed oxidation of naphthols 218 to generate 216 in situ. While no detailed mechanism has been proposed, based on prior work of Hawkins et
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Published 29 Sep 2020

The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization

  • Sharna-kay Daley and
  • Nadale Downer-Riley

Beilstein J. Org. Chem. 2020, 16, 2026–2031, doi:10.3762/bjoc.16.169

Graphical Abstract
  • ), was subjected to the oxidants activated carbon (Act-C), potassium ferricyanide (K3[Fe(CN)6]), p-benzoquinone and stannic chloride (SnCl4). As shown in Scheme 4, with the exception of SnCl4, all oxidants resulted in the re-oxidation of the hydroxylated substrate to naphthoquinone 7. SnCl4, however
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Published 18 Aug 2020

Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules

  • Valerian Dragutan,
  • Ileana Dragutan,
  • Albert Demonceau and
  • Lionel Delaude

Beilstein J. Org. Chem. 2020, 16, 738–755, doi:10.3762/bjoc.16.68

Graphical Abstract
  • method, an enyne precursor was first converted into an exocyclic 1,3-diene in 92% yield. A Diels–Alder reaction with naphthoquinone and a deprotection step then led to the final compound (−)-zenkequinone B in a stereoselective manner (Scheme 23). C-Aryl glycosides Another interesting report from
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Published 16 Apr 2020

First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones

  • Grzegorz Mlostoń,
  • Katarzyna Urbaniak,
  • Paweł Urbaniak,
  • Anna Marko,
  • Anthony Linden and
  • Heinz Heimgartner

Beilstein J. Org. Chem. 2018, 14, 1834–1839, doi:10.3762/bjoc.14.156

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  • 1,4-benzoquinone, 1,4-naphthoquinone, and 1,4-anthraquinone were investigated as a route to novel 4H-thiochromene-5,8-dione derivatives. Results and Discussion Aryl and hetary lthiochalcones 1a–d are easily obtained by treatment of the corresponding chalcones with Lawesson′s reagent in THF solution
  • [15]. Along with the commercially available 1,4-benzoquinone (2a) and 1,4-naphthoquinone (2b), 1,4-anthraquinone (2c) and 5-chloro-10-hydroxy-1,4-anthraquinone (2d) were prepared from quinizarine according to known procedures [27][28]. First experiments were performed with 2b and thiochalcones 1a–d in
  • -Benzoquinone (2a) and 1,4-naphthoquinone (2b) were commercial reagents and used without further purification. 1,4-Anthraquinone (2c) was prepared from commercial quinizarine by treatment with sodium borohydride according to a literature procedure [27]. 5-Chloro-10-hydroxy-1,4-anthraquinone (2d) was obtained by
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Published 19 Jul 2018

Synthesis of spirocyclic scaffolds using hypervalent iodine reagents

  • Fateh V. Singh,
  • Priyanka B. Kole,
  • Saeesh R. Mangaonkar and
  • Samata E. Shetgaonkar

Beilstein J. Org. Chem. 2018, 14, 1778–1805, doi:10.3762/bjoc.14.152

Graphical Abstract
  • of palmarumycin CP1 were synthesized later which were showing good thioredoxin–thioredoxin reductase (Trx-1/TrxR) inhibitory activity [129]. It was observed that the introduction of enone functionality in naphthoquinone spiroketal enhances the biological activity of palmarumycin 138. Furthermore, Ley
  • pathway for the synthesis of the naturally occurring antibiotic platensimycin (154) which is isolated from Streptomyces platensis. In this report, 6-methoxy-1,4-naphthoquinone-4-ethylene ketal (153) was synthesized by intermolecular oxidative cyclization of 7-methoxy-α-naphthol (152) with ethylene glycol
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Published 17 Jul 2018

One hundred years of benzotropone chemistry

  • Arif Dastan,
  • Haydar Kilic and
  • Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

Graphical Abstract
  • depicted in Scheme 38 (Scheme 45) [161]. Sato’s group reported the synthesis of 7-hydroxy-2,3-benzotropone (241) via the ring expansion pathway of β-naphthoquinone (280) with diazomethane under various conditions and hydrolysis steps (Scheme 46) [169]. The boron trifluoride etherate-promoted ring expansion
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Published 23 May 2018

An air-stable bisboron complex: a practical bidentate Lewis acid catalyst

  • Longcheng Hong,
  • Sebastian Ahles,
  • Andreas H. Heindl,
  • Gastelle Tiétcha,
  • Andrey Petrov,
  • Zhenpin Lu,
  • Christian Logemann and
  • Hermann A. Wegner

Beilstein J. Org. Chem. 2018, 14, 618–625, doi:10.3762/bjoc.14.48

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  • acid catalyst B (25.0 µmol, 5.00 mol %) and 1,2,4,5-tetrazine (5.00 equiv) in CF3Ph (2.5 mL) were thoroughly stirred for several minutes. Then, 1,4-naphthoquinone (1.00 equiv) was added, the reaction mixture was heated at 110 °C for 20 h. The solvent, together with the excess of 1,2,4,5-tetrazine were
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Published 13 Mar 2018

Mannich base-connected syntheses mediated by ortho-quinone methides

  • Petra Barta,
  • Ferenc Fülöp and
  • István Szatmári

Beilstein J. Org. Chem. 2018, 14, 560–575, doi:10.3762/bjoc.14.43

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  • , mutagenous properties were also shown. Freccero et al. examined the photogeneration by laser flash photolysis and reactivity of naphthoquinone methides as well as their activity as purine selective DNA alkylating agents [93]. Farrell et al. studied the mechanism of the cytotoxic action of naphthoquinone
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Published 06 Mar 2018

Design and synthesis of propellane derivatives and oxa-bowls via ring-rearrangement metathesis as a key step

  • Sambasivarao Kotha and
  • Rama Gunta

Beilstein J. Org. Chem. 2015, 11, 1727–1731, doi:10.3762/bjoc.11.188

Graphical Abstract
  • from readily accessible starting materials such as p-benzoquinone, 1,4-naphthoquinone and 1,4-anthraquinone. Keywords: allylation; propellane derivatives; quinones; ring-rearrangement metathesis; Introduction The synthesis of complex target structures requires bond-disconnection analysis of the
  • -quinones (p-benzoquinone, 1,4-naphthoquinone or 1,4-anthraquinone) with a freshly cracked cyclopentadiene. To realize the synthetic strategy (Figure 1) to various propellane derivatives [29][30][31] and oxa-bowls, we commenced with the preparation of a known DA adduct 3a [32]. Subsequent allylation of 3a
  • compounds 2a and 1a have been confirmed on the basis of 1H, 13C NMR and DEPT-135 spectral data and further supported by HRMS data. To expand the strategy, another DA adduct 3b was prepared from the commercially available 1,4-naphthoquinone and freshly cracked cyclopentadiene by following the literature
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Published 24 Sep 2015

Spiro annulation of cage polycycles via Grignard reaction and ring-closing metathesis as key steps

  • Sambasivarao Kotha,
  • Mohammad Saifuddin,
  • Rashid Ali and
  • Gaddamedi Sreevani

Beilstein J. Org. Chem. 2015, 11, 1367–1372, doi:10.3762/bjoc.11.147

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  • -pyrano cage compound 7 involving ring-closing metathesis is reported. The hexacyclic dione 10 was prepared from simple and readily available starting materials such as 1,4-naphthoquinone and cyclopentadiene. The synthesis of an unprecedented octacyclic cage compound through intramolecular Diels–Alder (DA
  • 10 could be constructed in two steps from readily available starting materials such as 1,4-naphthoquinone (9) and cyclopentadiene (8) [40][41]. Results and Discussion In connection with the synthesis of new cage molecules, we reported a new approach to the hexacyclic dione 10 and related systems via
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Published 05 Aug 2015

A new and efficient procedure for the synthesis of hexahydropyrimidine-fused 1,4-naphthoquinones

  • Marcelo Isidoro P. Reis,
  • Vinícius R. Campos,
  • Jackson A. L. C. Resende,
  • Fernando C. Silva and
  • Vitor F. Ferreira

Beilstein J. Org. Chem. 2015, 11, 1235–1240, doi:10.3762/bjoc.11.137

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  • ]quinazoline; microwave; naphthoquinone; 1,3-quinazoline; 1,3,5-triazinane; Introduction Quinones represent a diverse family of naturally occurring secondary metabolites [1][2][3]. Interest in these substances has intensified in recent years due to their pharmacological importance [4]. Heterocycle-fused
  • demonstrated to display various biological activities. There are several specific and general methods reported in the literature that describe the preparation and biological activity of heterocycle-fused naphthoquinone compounds [35]. Recently, Iida et al. described a general method for the construction of
  • unsymmetrical hexahydropyrimidine-fused 1,2- and 1,4-naphthoquinones by the reaction of 4-amino-l,2-naphthoquinone and 2-amino-1,4-naphthoquinone with amines and formaldehyde in moderate yields [37]. Ohta et al. studied the nucleophilic addition reaction of methylamine to 2-bromo-3-hydroxymethyl-1,4
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Published 22 Jul 2015

Glycoluril–tetrathiafulvalene molecular clips: on the influence of electronic and spatial properties for binding neutral accepting guests

  • Yoann Cotelle,
  • Marie Hardouin-Lerouge,
  • Stéphanie Legoupy,
  • Olivier Alévêque,
  • Eric Levillain and
  • Piétrick Hudhomme

Beilstein J. Org. Chem. 2015, 11, 1023–1036, doi:10.3762/bjoc.11.115

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  • molecular clip 2 in 48% yield using similar experimental conditions. Whereas the synthesis of molecular clips 1, 2 and 3 uses the nucleophilic substitution onto diphenylglycoluril 5 as a key-step, the introduction of the naphthoquinone spacer in clip 4 required the previous transformation of compound 5 into
  • -empirical AM1 method in the case of 4 [19]. This distance was estimated to be equal to 9.7 Å indicating that this enlargement around 2 Å was the result mainly of the spatial contribution of the additional naphthoquinone spacer in molecular clip 4. Electrochemical properties The electrochemical behaviour of
  • intermolecular electronic interactions between them. It should be noted that the electroactive naphthoquinone acceptor group incorporated in the spacer unit is characterized by a reduction wave (Eapp0red1) at −1.05 V vs Fc+/Fc. On the contrary, the CV of clips 1–3 shows a significant splitting of the first
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Published 17 Jun 2015

Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water”

  • Julio Benites,
  • Juan Meléndez,
  • Cynthia Estela,
  • David Ríos,
  • Luis Espinoza,
  • Iván Brito and
  • Jaime A. Valderrama

Beilstein J. Org. Chem. 2014, 10, 2448–2452, doi:10.3762/bjoc.10.255

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  • de Química, Universidad Técnica Federico Santa María, Casilla 110-V, Valparaíso, Chile Departamento de Química, Facultad de Ciencias Básicas Universidad de Antofagasta, Casilla 170, Antofagasta, Chile 10.3762/bjoc.10.255 Abstract A number of N-phenyl-1,4-naphthoquinone monoimines 6–10 were prepared
  • conventional oxidative phenylamination procedures, this novel synthetic method offers the advantage of aerobic conditions “on water” instead of hazardous oxidant reagents currently employed in aqueous alcoholic media. Keywords: 1,4-naphthoquinone monoimines; on water; oxidative coupling; rose bengal; solar
  • [1][2][3][4][5][6]. In this context, the sunlight-induced synthesis of 5-hydroxy-1,4-naphthoquinone (2, juglone, Figure 1) by sensitized phothooxygenation of 1,5-dihydroxynaphthalene (1, 1,5-DHN) [7] and the preparation of 2-phenylamino-1,4-naphthoquinones by reaction of 1,4-naphthoquinones with
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Published 22 Oct 2014

Boron-substituted 1,3-dienes and heterodienes as key elements in multicomponent processes

  • Ludovic Eberlin,
  • Fabien Tripoteau,
  • François Carreaux,
  • Andrew Whiting and
  • Bertrand Carboni

Beilstein J. Org. Chem. 2014, 10, 237–250, doi:10.3762/bjoc.10.19

Graphical Abstract
  • presence of Yb(fod)3 to afford 2-alkoxy-3,4-dihydro-5-vinyl-2H-pyran 33. In the presence of electron-poor dienophiles, as N-phenylmaleimide, maleic anhydride, activated azo compounds or naphthoquinone, 33 underwent normal Diels–Alder reactions thus giving the corresponding cycloadducts 34 as single
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Published 22 Jan 2014

New hydrogen-bonding organocatalysts: Chiral cyclophosphazanes and phosphorus amides as catalysts for asymmetric Michael additions

  • Helge Klare,
  • Jörg M. Neudörfl and
  • Bernd Goldfuss

Beilstein J. Org. Chem. 2014, 10, 224–236, doi:10.3762/bjoc.10.18

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  • to 2-hydroxy-1,4-naphthoquinone With these novel catalysts in hands we tested their efficiency in enantioselective catalysis. The reaction of 2-hydroxy-1,4-naphthoquinone (17) with β-nitrostyrene (18) is well-suited for comparison because it has already been studied while employing thiourea
  • addition of 2-hydroxy-1,4-naphthoquinone to trans-β-nitrostyrene: To a stirred mixture of 2-hydroxy-1,4-naphthoquinone (34.8 mg, 0.2 mmol) and trans-β-nitrostyrene (32.8 mg, 0.22 mmol) in dry DCM (1.2 mL) was added catalyst 14a (11.8 mg, 0.02 mmol) and stirred for 3 h at room temperature. After completion
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Published 21 Jan 2014

The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids

  • Tatyana L. Pavlovskaya,
  • Fedor G. Yaremenko,
  • Victoria V. Lipson,
  • Svetlana V. Shishkina,
  • Oleg V. Shishkin,
  • Vladimir I. Musatov and
  • Alexander S. Karpenko

Beilstein J. Org. Chem. 2014, 10, 117–126, doi:10.3762/bjoc.10.8

Graphical Abstract
  • nonnatural α-amino acids [11][12][13], more than fifteen isatins [14], and 1,3-dipolarophiles, e.g. α,β-unsaturated ketones [15][16][17], maleimides [18][19], benzo[b]thiophene-1,1-dioxide [20], bis(arylmethylidene)acetones and -cycloalkanones [21][22], 1,4-naphthoquinone [23], arylidenemalonodinitriles [24
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Published 09 Jan 2014
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