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Search for "ketones" in Full Text gives 610 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

High-pressure activation for the solvent- and catalyst-free syntheses of heterocycles, pharmaceuticals and esters

  • Kelsey Plasse,
  • Valerie Wright,
  • Guoshu Xie,
  • R. Bernadett Vlocskó,
  • Alexander Lazarev and
  • Béla Török

Beilstein J. Org. Chem. 2025, 21, 1374–1387, doi:10.3762/bjoc.21.102

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  • imidazole-based N-heterocyclic carbene (NHC)–CuCl complexes [40]. However, their synthesis is often tainted by the use of toxic reagents and solvents. In addition, when o-phenylenediamine reacts with ketones, the common catalytic methods yield benzodiazepine products [41]. In our case the reaction of o
  • -phenylenediamine with ketones to form 1,3-dihydrobenzimidazoles. Molecular volumes of the reactants and products and the reaction volume (ΔV) for the reaction of chalcone with hydrazines to form pyrazoles. Molecular volumes of the reactants and products and the reaction volume (ΔV) for the reaction of chalcone
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Published 02 Jul 2025

Oxetanes: formation, reactivity and total syntheses of natural products

  • Peter Gabko,
  • Martin Kalník and
  • Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

Graphical Abstract
  • base [5]. In fact, its hydrogen-bond-accepting ability is even stronger than that of the other 3-, 5- and 6-membered cyclic ethers, as well as the carbonyls of aldehydes, ketones, esters and carbonates [6][7][8]. The only better carbonyl-based hydrogen-bond acceptors are amides, carbamates and ureas [9
  • ] dimerisation, this methodology enables performing photocycloadditions between electron-deficient alkenes and aliphatic ketones which had been usually avoided. One year later, Yoon and co-workers published the first highly enantioselective Paternò–Büchi reaction between quinolones 84 and ketoesters 85 (Scheme
  • enantioselectivities. In 2018, Scheidt and colleagues disclosed the first N-heterocyclic carbene (NHC)-catalysed [2 + 2] annulation between trifluoromethyl ketones and γ-substituted allenoates (Scheme 25a) [68]. The resulting 2-alkylideneoxetane products 95 were generally obtained in >90% yields and good
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Published 27 Jun 2025

Recent advances in oxidative radical difunctionalization of N-arylacrylamides enabled by carbon radical reagents

  • Jiangfei Chen,
  • Yi-Lin Qu,
  • Ming Yuan,
  • Xiang-Mei Wu,
  • Heng-Pei Jiang,
  • Ying Fu and
  • Shengrong Guo

Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98

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  • , α-bromo ketones, and α-bromo nitriles, effectively participated in the reaction (88f–i). Even a more sterically hindered substrate also underwent successful cyclization affording 88j, thus further underscoring the robustness of this transformation. However, attempts using benzyl bromide, allyl
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Published 24 Jun 2025

Recent advances in synthetic approaches for bioactive cinnamic acid derivatives

  • Betty A. Kustiana,
  • Galuh Widiyarti and
  • Teni Ernawati

Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85

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Published 28 May 2025

Recent advances in controllable/divergent synthesis

  • Jilei Cao,
  • Leiyang Bai and
  • Xuefeng Jiang

Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73

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  • regulating the chemical selectivity of a three-component radical cascade reaction involving α-brominated aryl ketones 72, olefins 73, and 1-methylquinoxalin-2(1H)-one (74) with an inorganic base, they were able to obtain two important types of products with high yield and enantioselectivity. Through
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Published 07 May 2025

Regioselective formal hydrocyanation of allenes: synthesis of β,γ-unsaturated nitriles with α-all-carbon quaternary centers

  • Seeun Lim,
  • Teresa Kim and
  • Yunmi Lee

Beilstein J. Org. Chem. 2025, 21, 800–806, doi:10.3762/bjoc.21.63

Graphical Abstract
  • are important intermediates in organic syntheses because of the versatility of the cyano group, which can be readily transformed into a wide range of functional groups, including amides, carboxylic acids, amines, aldehydes, ketones, and N-heterocycles [6][7][8]. However, the synthesis of all-carbon
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Published 17 Apr 2025

Recent advances in the electrochemical synthesis of organophosphorus compounds

  • Babak Kaboudin,
  • Milad Behroozi,
  • Sepideh Sadighi and
  • Fatemeh Asgharzadeh

Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61

Graphical Abstract
  • or ketones. They used nickel foam as both anode and cathode electrodes in an undivided cell under air at room temperature. The reaction was carried out in the presence of KI as an electrolyte, a key additive, and acetone as a solvent. HI increases the reaction yield due to the activation of the
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Published 16 Apr 2025

New advances in asymmetric organocatalysis II

  • Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 766–769, doi:10.3762/bjoc.21.60

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  • describes the enantioselective Michael addition of pyrazoline-5-ones to α,β-unsaturated ketones. The enantioselectivity and chemical efficiency of this transformation were achieved with a cinchona-alkaloid-derived primary-amine–Brønsted acid composite [22]. A good demonstration of how organocatalysis
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Published 15 Apr 2025

Origami with small molecules: exploiting the C–F bond as a conformational tool

  • Patrick Ryan,
  • Ramsha Iftikhar and
  • Luke Hunter

Beilstein J. Org. Chem. 2025, 21, 680–716, doi:10.3762/bjoc.21.54

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Published 02 Apr 2025

Formaldehyde surrogates in multicomponent reactions

  • Cecilia I. Attorresi,
  • Javier A. Ramírez and
  • Bernhard Westermann

Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45

Graphical Abstract
  • developed in which the alkene compound has been replaced with other surrogates for electrophilic addition, such as ketones [32][33][34]. In the case of the carbonyl component, it is generally an aromatic aldehyde [30][33][34] and there are not many reports on using formaldehyde in the Povarov reaction. In a
  • , methyl aryl ketones, and DMSO under iron(III) catalysis and using K2S2O8 for its activation [39]. The proposed mechanism is very close to those described above, with the methyl aryl ketone taking part of the reaction in place of the styrene component in the Povarov cyclization. In this case, the imine
  • reaction, affording 2-arylquinolines III. All of these examples showed the versatility of DMSO as a methylene source in the synthesis of substituted quinoline compounds (structures I, II, and III; Scheme 8 and Scheme 9), using different substrates (such as styrenes, alkynes, and methyl aryl ketones) and
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Published 13 Mar 2025

Vinylogous functionalization of 4-alkylidene-5-aminopyrazoles with methyl trifluoropyruvates

  • Judit Hostalet-Romero,
  • Laura Carceller-Ferrer,
  • Gonzalo Blay,
  • Amparo Sanz-Marco,
  • José R. Pedro and
  • Carlos Vila

Beilstein J. Org. Chem. 2025, 21, 533–540, doi:10.3762/bjoc.21.41

Graphical Abstract
  • starting materials to study the vinylogous functionalization with alkyl trifluoropyruvates. The synthesis of compounds 3 was accomplished by the reaction of cyclic ketones 1 and 5-aminopyrazoles 2 in the presence of acetic acid (Scheme 1) [30][31]. Cyclohexenones 1a–c provided the corresponding products
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Published 10 Mar 2025

Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction

  • James Guevara-Pulido,
  • Fernando González-Pérez,
  • José M. Andrés and
  • Rafael Pedrosa

Beilstein J. Org. Chem. 2025, 21, 473–482, doi:10.3762/bjoc.21.34

Graphical Abstract
  • other Michael adducts prepared by reacting with differently activated ketones, the enantiomeric ratio of the isolated anti-diastereomer was excellent (entries 1 and 10–13, Table 5). Interestingly, the method also provides good resolution for Michael adducts 8 and 9 synthesized by reacting keto sulfones
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Published 03 Mar 2025

Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones

  • Yurii A. Sayapin,
  • Eugeny A. Gusakov,
  • Inna O. Tupaeva,
  • Alexander D. Dubonosov,
  • Igor V. Dorogan,
  • Valery V. Tkachev,
  • Anna S. Goncharova,
  • Gennady V. Shilov,
  • Natalia S. Kuznetsova,
  • Svetlana Y. Filippova,
  • Tatyana A. Krasnikova,
  • Yanis A. Boumber,
  • Alexey Y. Maksimov,
  • Sergey M. Aldoshin and
  • Vladimir I. Minkin

Beilstein J. Org. Chem. 2025, 21, 358–368, doi:10.3762/bjoc.21.26

Graphical Abstract
  • 2-(indolin-2-yl)-1,3-tropolones [5]. Unlike the cross-aldol reaction of o-chloranil with methyl ketones [13][14][15], which is always accompanied by the removal of one of the chlorine atoms from the seven-membered ring, the acid-catalyzed reaction between methylene-active heterocyclic compounds and
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Published 17 Feb 2025

Red light excitation: illuminating photocatalysis in a new spectrum

  • Lucas Fortier,
  • Corentin Lefebvre and
  • Norbert Hoffmann

Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22

Graphical Abstract
  • properties beyond 645 nm, providing access to low-energy red-light-driven chemical transformations. The catalysts have successfully facilitated the dehalogenation of 18 different α-halo ketones 33 with minimal catalyst loading (0.1 mol %) and high yields under mild conditions. For instance, bromoacetophenone
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Published 07 Feb 2025

Molecular diversity of the reactions of MBH carbonates of isatins and various nucleophiles

  • Zi-Ying Xiao,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2025, 21, 286–295, doi:10.3762/bjoc.21.21

Graphical Abstract
  • reactions of isatins with alkyl acrylates, acrylonitrile, and other activated alkenes [26][27][28][29]. Due to the stronger electron-withdrawing effect of the oxindole motif, MBH carbonates of isatins showed higher reactivity than that of the normal MBH carbonates of normal ketones [30][31][32][33][34][35
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Published 06 Feb 2025

Cu(OTf)2-catalyzed multicomponent reactions

  • Sara Colombo,
  • Camilla Loro,
  • Egle M. Beccalli,
  • Gianluigi Broggini and
  • Marta Papis

Beilstein J. Org. Chem. 2025, 21, 122–145, doi:10.3762/bjoc.21.7

Graphical Abstract
  • ]. Three-component coupling of amines, aldehydes or ketones, and terminal alkynes catalyzed by Cu(OTf)2 is a fruitful tool for the production of α-substituted propargylamines 10 (Scheme 7) [20]. The reaction involves the alkynylation of the corresponding imines formed in situ and provides higher yields
  • was crucial for the formation of the organozinc reagent (Scheme 19) [36]. Spiro-2,3-dihydroquinazolinones 26 were formed exploiting a one-pot multicomponent reaction, using isatoic anhydride, ketones and primary amines. The isolation of the amide intermediate XXIII obtained by the copper-catalyzed
  • of promoting the three-component cascade cyclization of 2-formylbenzonitriles, alkyl aryl ketones, and diaryliodonium salts to afford 2-arylisoindolinones 32 (Scheme 24) [41]. It is conceivable that the reaction starts with the formation of an N-arylnitrilium cation XXXI that, after hydrolysis
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Published 14 Jan 2025

Recent advances in organocatalytic atroposelective reactions

  • Henrich Szabados and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6

Graphical Abstract
  • biaryl ketones 84 with cyclohexanones 85 mediated by the second-generation chiral phosphoric acid C26 led to the formation of tetrahydroacridines 86 (Scheme 28) [52]. This Friedländer reaction provided products 86 in moderate to good yields with consistently high enantiomeric purities and high
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Published 09 Jan 2025

Non-covalent organocatalyzed enantioselective cyclization reactions of α,β-unsaturated imines

  • Sergio Torres-Oya and
  • Mercedes Zurro

Beilstein J. Org. Chem. 2024, 20, 3221–3255, doi:10.3762/bjoc.20.268

Graphical Abstract
  • reported, providing a novel methodology for the construction of α,β-unsaturated imines [4]. There are different types of α,β-unsaturated imines, such as the acyclic imines aldimines, ketimines, or dienimines, depending on whether they are derived from aldehydes, ketones, or doubly unsaturated ketones
  • demand aza-Diels–Alder reaction (IEDADA) of β,γ-unsaturated ketones 23 and benzofuran-derived azadienes 11 [31]. The procedure enables the straightforward synthesis of benzofuran derivatives 24 bearing an additional tetrahydropyridine ring in good yields (51–94%) and excellent enantioselectivities (90–96
  • ketones 42 [37]. With this transformation polysubstituted cyclohexanes 43 bearing four consecutive stereocenters are afforded through efficient one-pot cyclization with good yields (43–95%) and with high enantioselectivities (80–97% ee) (Scheme 15). In general, 1-azadienes 14 with different substitution
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Published 10 Dec 2024

Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies

  • Lucía Campos-Prieto,
  • Aitor García-Rey,
  • Eddy Sotelo and
  • Ana Mallo-Abreu

Beilstein J. Org. Chem. 2024, 20, 3151–3173, doi:10.3762/bjoc.20.261

Graphical Abstract
  • intramolecular SNAr reactions. Ugi-4CR/deprotection/cyclization (UDC) strategy: In the UDC approach a protected amine and an electrophilic functional group like esters or ketones are used. Convertible isocyanides can also be employed. Once the Ugi reaction is completed, the protecting group is removed, and the
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Published 03 Dec 2024

Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline N,N’-dioxide

  • Noble Brako,
  • Sreerag Moorkkannur Narayanan,
  • Amber Burns,
  • Layla Auter,
  • Valentino Cesiliano,
  • Rajeev Prabhakar and
  • Norito Takenaka

Beilstein J. Org. Chem. 2024, 20, 3069–3076, doi:10.3762/bjoc.20.255

Graphical Abstract
  • propargyltrichlorosilane [35][36] (Scheme 2). Other notable asymmetric catalytic approaches to prepare α-allenic alcohols (R2 = H) include the Corey–Bakshi–Shibata reduction of allenyl ketones [37], enzymatic [38][39][40], non-enzymatic [41] kinetic resolution of racemic α-allenic alcohols, and asymmetric 1,4
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Published 25 Nov 2024

Advances in radical peroxidation with hydroperoxides

  • Oleg V. Bityukov,
  • Pavel Yu. Serdyuchenko,
  • Andrey S. Kirillov,
  • Gennady I. Nikishin,
  • Vera A. Vil’ and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2024, 20, 2959–3006, doi:10.3762/bjoc.20.249

Graphical Abstract
  • ketones 108 and TBHP to alkenes 107 (Scheme 38a) [94] and methacrylamides and methacrylates 110 (Scheme 38b) [95] with the formation of γ-peroxyketones 109 and 112 have been demonstrated. The reactions are believed to proceed via thermal decomposition of alkenyl peroxide B, which is formed from geminal
  • in Fe-catalyzed difunctionalization of alkenes with TBHP resulting in δ-peroxy ketones 126 and δ-peroxy esters 129 (Scheme 43a and 43b). In the case of siloxy cyclopropanes 128 the authors used TBAF as the additive to remove the TMS-protecting group. Oxidation of the resulting anion A with TBHP and
  • and 134 with TBHP and aldehydes as alkyl sources, producing long-chain ketones 136 via intermediate peroxide 135 formation (Scheme 44b) [104]. Acyl fragment: A breakthrough on difunctionalization of C=C double bonds using TBHP and aldehyde has been achieved in 2011 by Li and co-workers (Scheme 45a
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Published 18 Nov 2024

gem-Difluorovinyl and trifluorovinyl Michael acceptors in the synthesis of α,β-unsaturated fluorinated and nonfluorinated amides

  • Monika Bilska-Markowska,
  • Marcin Kaźmierczak,
  • Wojciech Jankowski and
  • Marcin Hoffmann

Beilstein J. Org. Chem. 2024, 20, 2946–2953, doi:10.3762/bjoc.20.247

Graphical Abstract
  • of 1-fluorobis(phenylsulfonyl)methane (FBSM) to α,β-unsaturated ketones with cinchona alkaloids [9]. Fluorinated Michael acceptors usually contain one fluorine atom or a trifluoromethyl group in the structure [10][11][12]. There are also known examples of gem-difluoroalkenes being used as Michael
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Published 15 Nov 2024

Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

  • Ritu Mamgain,
  • Kokila Sakthivel and
  • Fateh V. Singh

Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243

Graphical Abstract
  • various substituents on the aromatic ring. Additionally, a variety of substituted esters, ketones, and nitriles were found to be compatible with the reaction. Additionally, the same approach was used for the aryl sulfonylation. Trisubstituted allylic sulfones 35 were synthesized by reacting MBH acetate 33
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Published 13 Nov 2024

Mechanochemical difluoromethylations of ketones

  • Jinbo Ke,
  • Pit van Bonn and
  • Carsten Bolm

Beilstein J. Org. Chem. 2024, 20, 2799–2805, doi:10.3762/bjoc.20.235

Graphical Abstract
  • Jinbo Ke Pit van Bonn Carsten Bolm Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany 10.3762/bjoc.20.235 Abstract We present a mechanochemical synthesis of difluoromethyl enol ethers. Utilizing an in situ generation of difluorocarbenes, ketones are
  • by these findings, we now explored difluoromethylation reactions with compounds bearing less nucleophilic functional groups. Ketones caught our particular attention as they contain a weak nucleophilic carbonyl oxygen adjacent to an electrophilic carbonyl carbon. Previous studies have focused on
  • sodium fluoride catalyst, with simple ketones, which resulted in the formation of difluoromethyl 2,2-difluorocyclopropyl ethers (Scheme 1B). Although the reactions worked well, it is also noteworthy that the use of TFDA as reagent, liberated fluoro(trimethyl)silane (TMSF), carbon dioxide, and ozone
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Published 04 Nov 2024

Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction

  • Yuta Kabumoto,
  • Eiichiro Yoshimoto,
  • Bing Xiaohuan,
  • Masato Morita,
  • Motohiro Yasui,
  • Shigeyuki Yamada and
  • Tsutomu Konno

Beilstein J. Org. Chem. 2024, 20, 2776–2783, doi:10.3762/bjoc.20.233

Graphical Abstract
  • fluoroalkylated amines 15 with high optical purity could be easily prepared through [1,3]-proton shift reactions of optically active imines 14 which in turn were readily synthesized by condensation of various perfluoroalkyl ketones with optically active (R)-1-phenylethylamine (Scheme 2a) [25][26][27][28][29][30
  • ][31][32]. Therefore, we envisioned that optically active tetrafluoroethylenated amines 17 could be synthesized by applying the [1,3]-proton shift to optically active imines 16 derived from readily prepared tetrafluoroethylenated ketones (Scheme 2b). In this paper, we describe the details of the [1,3
  • chlorides in the presence of a copper catalyst to afford the corresponding tetrafluoroethylenated ketones 19. The ketones were then condensed with (R)-1-phenylethylamine under the influence of TiCl4 [34][35] to prepare various optically active imines (R)-16 in high yields (Scheme 3). Based on the result of
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Published 01 Nov 2024
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