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Search for "synthesis" in Full Text gives 3619 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Synthesis of electrophile-tethered preQ1 analogs for covalent attachment to preQ1 RNA

  • Laurin Flemmich and
  • Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 483–489, doi:10.3762/bjoc.21.35

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  • haloalkyl- and mesylate-modified preQ1 3a and 3b, the corresponding variants with different Watson–Crick face of DPQ1 (4a–e), as well as to the nucleobase precursors preQ1 (1) and DPQ1 (2), respectively. Results and Discussion Synthesis of preQ1 and DPQ1 Several synthetic strategies towards preQ1 and its
  • -step synthesis of O6-methyl preQ1 (16, m6preQ1) [28]. The direct reduction of the precursor O6-methyl preQ0 (15, m6preQ0) was possible, eliminating the need for the previously introduced protection/solubility concept, which shortened the synthetic route to only four steps (Supporting Information File 1
  • ). Synthesis of preQ1 and DPQ1 derivatives with electrophilic handles For the synthesis of haloalkyl- and mesyloxyalkyl-modified preQ1 and DPQ1 ligands 3a,b and 4a–e (for target structures see Scheme 1), a divergent synthetic route was sought that provided flexibility with respect to linker length and nature
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Published 04 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

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  • yields [27]. These reactions have been utilized in the enantioselective synthesis of aryl sulfoxides through the arylation of sulfonate anions in the presence of palladium catalysts [28][29]. They have also been used in the synthesis of the neuraminidase inhibitor (−)-oseltamivir [30] and the
  • organocatalytic synthesis of 2-cyclohexen-1-ones via a Michael/Michael/retro-Michael cascade reaction [31]. Our research has shown that the Jørgensen–Hayashi catalyst [32][33] is a highly promising organocatalyst, facilitating enantioselective Michael addition reactions with high yields and excellent levels of
  • enantiocontrol [34][35][36][37][38][39]. In our studies on the organocatalytic enantioselective synthesis of 1,5-ketoaldehydes [40], we found that the prolinol derivative A is an outstanding catalyst for the enantioselective preparation of these adducts (Scheme 2). We are currently investigating whether this
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Published 03 Mar 2025

Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions

  • Francesco Mele,
  • Ana M. Constantin,
  • Andrea Porcheddu,
  • Raimondo Maggi,
  • Giovanni Maestri,
  • Nicola Della Ca’ and
  • Luca Capaldo

Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33

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  • Sustainability, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy 10.3762/bjoc.21.33 Abstract Photomechanochemistry, i.e., the merger of light energy and mechanical forces, is emerging as a new trend in organic synthesis, enabling unique reactivities of fleeting excited states under solvent
  • research. Keywords: light-mediated synthesis; mechanochemistry; photomechanochemistry; Introduction Light-mediated synthetic methodologies have significantly transformed contemporary organic chemistry by enabling a broad array of previously unattainable transformations [1]. In fact, the absorption of a
  • turn demands large volumes of solvents, negatively impacting the sustainability of light-mediated synthesis as it transitions from academic curiosity to industrial application. Moreover, since the solvent is the reaction component with the highest concentration, competitive side-reactions such as
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Published 03 Mar 2025

Electrochemical synthesis of cyclic biaryl λ3-bromanes from 2,2’-dibromobiphenyls

  • Andrejs Savkins and
  • Igors Sokolovs

Beilstein J. Org. Chem. 2025, 21, 451–457, doi:10.3762/bjoc.21.32

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  • Andrejs Savkins Igors Sokolovs Latvian Institute of Organic Synthesis, Aizkraukles 21, 1006 Riga, Latvia Faculty of Medicine and Life Sciences, University of Latvia, Jelgavas 1, 1004 Riga, Latvia 10.3762/bjoc.21.32 Abstract The remarkable nucleofugality of bromoarenes in diarylbromonium species
  • an electrochemical synthesis of cyclic diaryl λ3-bromanes under anodic oxidation conditions. Results and Discussion Symmetric 2,2'-dibromo-1,1'-biphenyl 4a possessing ethoxycarbonyl groups ortho to the bromine was chosen as a model compound for our study. We anticipated that the presence of the ester
  • moiety would help to stabilize the key λ3-bromane(III) intermediate 5, as demonstrated in the work of Miyamoto et al. [21], thus facilitating its formation in anodic oxidation. The anodic oxidation of 4a under previously published conditions for the synthesis of Br(III) species [16][18] (GC as working
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Published 27 Feb 2025

New tandem Ugi/intramolecular Diels–Alder reaction based on vinylfuran and 1,3-butadienylfuran derivatives

  • Yuriy I. Horak,
  • Roman Z. Lytvyn,
  • Andrii R. Vakhula,
  • Yuriy V. Homza,
  • Nazariy T. Pokhodylo and
  • Mykola D. Obushak

Beilstein J. Org. Chem. 2025, 21, 444–450, doi:10.3762/bjoc.21.31

Graphical Abstract
  • managed to carry out these two tandem reactions in one-pot, and, thus, proposed a new variant of the Ugi/Diels–Alder tandem reaction, which is highly variable and promising for implementation in combinatorial synthesis. State of the art of Ugi/Diels–Alder reaction based on furan. Preparation of 4,4a
  • ,5,6,7,7a-hexahydro-3aH-furo[2,3-f]isoindoles via Ugi/IMDAV tandem reaction. Kinetic product 5 does not transform into thermodynamic product 6. Synthesis of compounds 6a. Synthesis of compound 7. Synthesis of compounds 9. Supporting Information Supporting Information File 4: Experimental procedures
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Published 26 Feb 2025

Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages

  • Keith G. Andrews

Beilstein J. Org. Chem. 2025, 21, 421–443, doi:10.3762/bjoc.21.30

Graphical Abstract
  • been inspired to understand and mimic these accelerations and selectivities for applications in catalysis for sustainable synthesis. Over the past 60+ years, mimicry strategies have evolved with changing interests, understanding, and synthetic advances but, ubiquitously, research has focused on use of
  • mixtures of ring sizes, either by enzymatic synthesis (cyclodextrins) or thermodynamic synthesis, and are used after separation of the different ring sizes. Since the macrocycles are generically hydrophobic on the interior, they can perform catalysis by dual-confinement of two hydrophobic substrates from
  • smaller reagents. Also in the category of (functionalized) macrocycles are large enzyme models, such as those reported by Cram [65][86][87][88], Breslow [74][75][89][90][91][92], Diederich [93], and others [94][95][96], constructed by (often laborious) linear synthesis to afford more elaborate
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Published 24 Feb 2025

Unraveling aromaticity: the dual worlds of pyrazole, pyrazoline, and 3D carborane

  • Zahra Noori,
  • Miquel Solà,
  • Clara Viñas,
  • Francesc Teixidor and
  • Jordi Poater

Beilstein J. Org. Chem. 2025, 21, 412–420, doi:10.3762/bjoc.21.29

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  • cage retains its aromatic character, the pyrazole’s aromaticity is lost. As a result, rather than forming o-carborane-fused pyrazoles, the synthesis yielded o-carborane-fused pyrazolines, which are non-aromatic. The limited overlap between the π molecular orbitals (MOs) of the planar heterocycle and
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Published 21 Feb 2025

Identification and removal of a cryptic impurity in pomalidomide-PEG based PROTAC

  • Bingnan Wang,
  • Yong Lu and
  • Chuo Chen

Beilstein J. Org. Chem. 2025, 21, 407–411, doi:10.3762/bjoc.21.28

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  • drug”) class of PROTAC molecules with a PEG linker is frequently used to promote targeted protein degradation. The standard protocol for their synthesis involves nucleophilic aromatic substitution of 4-fluorothalidomide with a PEG-amine. We report herein the identification of a commonly ignored
  • impurity generated in this process. Nucleophilic acyl substitution competes with aromatic substitution to displace glutarimide and gives a byproduct that can co-elute with the desired product on HPLC throughout the remainder of the synthesis. Scavenging with taurine is a convenient way to minimize this
  • synthesis of iVeliparib-AP6 [5] starts with a nucleophilic aromatic substitution (SNAr) reaction wherein 4-fluorothalidomide (1) reacts with amino-PEG7-OH 2 to give alcohol 3 (Scheme 1). Subsequent alcohol oxidation followed by reductive amination of the resulting aldehyde 4 with veliparib [6][7] provides
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Published 18 Feb 2025

The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation

  • Rituparna Das and
  • Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27

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  • multistep synthesis of complex oligosaccharides and in turn, standardise the process of the glycosylation towards a particular stereochemical output. While neighbouring group participation has been quite effective in achieving the required stereochemistry of the produced glycosides, remote participation
  • glycoside 8 (Scheme 1). Glycosylation is considered as the most crucial step in any oligosaccharide synthesis, although it may be argued that, building block preparations or final deprotection steps remain equally demanding. The main challenge of glycosylation lies in the structural complexity of the
  • in attaining the required stereospecific glycosylation outputs. Apart from the widely convenient stepwise synthesis, recently one-pot glycosylations have also made an important mark which minimise the tedious purification of the intermediate molecules in each step [53][54][55][56][57][58]. In the
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Published 17 Feb 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
  • antibacterial [4] and cytotoxic activity [6][7]. Existing approaches to the synthesis of 1,3-tropolone derivatives have a number of drawbacks, namely, limited synthesis methodology and low yields of the target compounds [8][9][10][11][12][13][14][15]. Over the past decade, only a few reports have been published
  • o-chloranil depends on the reaction conditions and can proceed with or without the inclusion of a dehydrochlorination stage and leads to 5,6,7-trichloro- or 4,5,6,7-tetrachlorotropones, respectively [5][25]. The present work reports the synthesis of new 2-(indolin-2-yl)-1,3-tropolones by the
  • are localized in the Fourier synthesis of the difference electron density, then the coordinates and isotropic thermal parameters of all H atoms were calculated by the LSP using the “rider” model [33]. The absolute shifts of all 247 varied structure parameters were less than 0.001 σ, the final value of
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Published 17 Feb 2025

Synthesis, characterization, antimicrobial, cytotoxic and carbonic anhydrase inhibition activities of multifunctional pyrazolo-1,2-benzothiazine acetamides

  • Ayesha Saeed,
  • Shahana Ehsan,
  • Muhammad Zia-ur-Rehman,
  • Erin M. Marshall,
  • Sandra Loesgen,
  • Abdus Saleem,
  • Simone Giovannuzzi and
  • Claudiu T. Supuran

Beilstein J. Org. Chem. 2025, 21, 348–357, doi:10.3762/bjoc.21.25

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  • 10.3762/bjoc.21.25 Abstract The advent of antibiotic resistance in microorganisms requires the discovery and synthesis of novel antibiotics. At the same time, human pathogens are contributing to chronic and persistent inflammation. Motivated by these two concerning issues, new antibiotic drug candidates
  • [4]. Notable previous efforts include the synthesis of benzothiazine scaffolds connected to other heterocyclic moieties such as piperazine [5], triazole [6][7], hydantoin [8], and pyrazole moieties [9][10]. Very few examples of pyrazolobenzothiazines presenting an amide moiety are published. This
  • work covers the synthesis of synergistic scaffolds containing biologically active 1,2-benzothiazine, pyrazole, and amide moieties. 1,2-Benzothiazines are chemically gifted drug candidates. Since one of the very first synthesis in 1956 [11], these scaffolds have proved themselves as versatile and
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Published 12 Feb 2025

Synthesis of new condensed naphthoquinone, pyran and pyrimidine furancarboxylates

  • Kirill A. Gomonov,
  • Vasilii V. Pelipko,
  • Igor A. Litvinov,
  • Ilya A. Pilipenko,
  • Anna M. Stepanova,
  • Nikolai A. Lapatin,
  • Ruslan I. Baichurin and
  • Sergei V. Makarenko

Beilstein J. Org. Chem. 2025, 21, 340–347, doi:10.3762/bjoc.21.24

Graphical Abstract
  • furopyran, furocoumarin [9][10], and furopyrimidine series [11][12]. It is known that the main approaches to the synthesis of naphtho[2,3-b]furan-4,9-diones are reactions of hydroxynaphthalene-1,4-dione with ethane-1,2-diol [13], chloroacetaldehyde [14], ethenyl methyl sulfone [15], or ethenyl acetate [16
  • ]. In addition, we have previously demonstrated the effective use of alkyl 3-bromo-3-nitroacrylates in the preparation of condensed furancarboxylates using potassium acetate as a catalyst [28][29][30]. The present study is aimed at developing methods for the synthesis of a wide range of condensed
  • furancarboxylates based on the interaction of alkyl 3-bromo-3-nitroacrylates [31] with carbo- and heterocyclic CH-acids of the naphthoquinone, pyran, and pyrimidine series. Results and Discussion We have proposed a synthesis of dihydronaphthofuran-3-carboxylates based on the interaction of alkyl 3-bromo-3
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Published 12 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
  • deeper penetration through the reaction media, making the method highly scalable. In a batch reaction, the authors have successfully scaled up the synthesis by two orders of magnitude, achieving comparable yields without the need for complex flow reactors. The successful implementation of osmium
  • ability to operate under low-energy light conditions, opens up new avenues for main-group redox catalysis in organic synthesis. By leveraging light excitation to enhance the reducing power of the bismuth complex, the study showcases the potential of main-group photoredox systems to complement traditional
  • significant attention for their unique photophysical characteristics and versatility in NIR-driven reactions [51]. Cyanins consist of nitrogen-containing heterocycles connected by a polymethin chain [52][53], whose synthesis and modifications have been widely explored [54][55][56]. Such compounds exhibit
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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
  • have made them to become valuable building blocks in organic synthesis. Nucleophilic additions or spiroannulation of the highly reactive carbonyl group at the C-3 position of isatins have various fascinating applications in organic synthesis, which allowed transformation of isatins into various
  • - and P-containing nucleophiles to MBH carbonates of isatins and convenient synthesis of diverse functionalized 3-substituted oxindole derivatives. Results and Discussion Initially, the reaction conditions were briefly examined by using MBH nitrile of isatin 1a and p-toluidine (2a) as model reaction. It
  • also led to the development of a synthetic protocol for the convenient synthesis of 30 diversely substituted oxindole derivatives. Single crystal structure of compound 5a. Single crystal structure of compound 5j. Single crystal structure of compound 6e. Single crystal structure of compound 7a. Single
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Published 06 Feb 2025

Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[rst]pentaphene

  • Islam S. Marae,
  • Jingyun Tan,
  • Rengo Yoshioka,
  • Zakaria Ziadi,
  • Eugene Khaskin,
  • Serhii Vasylevskyi,
  • Ryota Kabe,
  • Xiushang Xu and
  • Akimitsu Narita

Beilstein J. Org. Chem. 2025, 21, 270–276, doi:10.3762/bjoc.21.19

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  • of zigzag and armchair edges, which may serve as a key building block for obtaining multifunctional organic materials [7]. Since the initial synthesis of BPP by Scholl and Neumann [8], simplified synthetic methods for BPP have been reported over the past decades [9][10][11][12][13][14]. Recently, a
  • Supporting Information File 1), suggesting that the BPP core can lead to such rod-shaped crystals and nanowires. Conclusion In summary, we achieved a facile synthesis of BPP-OiPr 3 and studied its optical properties in comparison to pristine BPP 2 and its oxidation product BPP-dione 4. Both BPP-OiPr 3 and
  • variety in crystallization, including differences in shape, length, and width, b) rod-like crystals with lengths of hundreds of nanometers, c) rod-like crystals with lengths of hundreds of micrometers, and d) longer wire. Synthesis of BPP-OiPr 3 and BPP-dione 4. Reaction conditions for the synthesis of
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Published 04 Feb 2025

Three-component reactions of conjugated dienes, CH acids and formaldehyde under diffusion mixing conditions

  • Dmitry E. Shybanov,
  • Maxim E. Kukushkin,
  • Eugene V. Babaev,
  • Nikolai V. Zyk and
  • Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 262–269, doi:10.3762/bjoc.21.18

Graphical Abstract
  • ), 115.0, 85.6, 39.3, 37.8, 27.4; HRMS–ESI+ (m/z): [M + H]+ calcd for C21H19O2, 303.1380; found, 303.1383. Equipment for carrying out reactions by the diffusion mixing method. Knoevenagel and Diels–Alder reactions in the multicomponent synthesis of substituted cyclohexadienes under formaldehyde
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Published 04 Feb 2025

Synthesis of disulfides and 3-sulfenylchromones from sodium sulfinates catalyzed by TBAI

  • Zhenlei Zhang,
  • Ying Wang,
  • Xingxing Pan,
  • Manqi Zhang,
  • Wei Zhao,
  • Meng Li and
  • Hao Zhang

Beilstein J. Org. Chem. 2025, 21, 253–261, doi:10.3762/bjoc.21.17

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  • groups in organic synthesis [1][2][3][4]. In chemistry and biology, disulfide bonds play crucial roles in protein folding and stabilization [5][6][7][8] and in the rubber industry, they are used to link different polymer chains [9][10]. The disulfide bond backbone is commonly used as a linker for
  • antibody–drug coupling (ADCs), in which the active drug released in the target cell by selectively breaking the disulfide bond [11]. Given the wide applicability of disulfides, the development of efficient, green, mild, and cost-effective methods for the organic synthesis of disulfides is of significant
  • importance. In the field of disulfide synthesis, the conventional approach mainly involves oxidizing thiols to form disulfides. This process employs various oxidation agents, which can be categorized as nonmetallic and metal derivatives [12][13][14][15][16]. Over the past few years, the implementation of
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Published 03 Feb 2025

Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory

  • Misato Suganuma,
  • Daichi Kitagawa,
  • Shota Hamatani and
  • Seiya Kobatake

Beilstein J. Org. Chem. 2025, 21, 242–252, doi:10.3762/bjoc.21.16

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  • solution samples were not degassed. The temperature control for UV–vis absorption spectral measurements was carried out using a UNISOKU CoolSpek UV/CD or an Ocean Optics CUV-QPOD. Material Synthesis of compounds N4 and I1–I4 The synthesis of the compounds is shown in Scheme 2. 4-Methyl-5
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Published 31 Jan 2025

Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles

  • Yujun Pang,
  • Jinglan Yan,
  • Nawaf Al-Maharik,
  • Qian Zhang,
  • Zeguo Fang and
  • Dong Li

Beilstein J. Org. Chem. 2025, 21, 234–241, doi:10.3762/bjoc.21.15

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  • −), respectively (Scheme 1a). Despite these advances, the above methods still suffer from several limitations, including a narrow substrate scope, the reliance on expensive metal catalysts and excess additives, and the need for multistep synthesis of difluoromethylating reagents. These drawbacks restrict their
  • -effectiveness, position it as a valuable strategy in drug design and the synthesis of fluorinated compounds. Selected examples containing tricyclic imidazole, CF2H or PhCF2 group. Strategies for the synthesis of difluoromethylated and difluoroarylmethylated tricyclic imidazoles. Substrate scope of the protocol
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Published 30 Jan 2025

Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization

  • Asahi Kanno,
  • Ryo Tanifuji,
  • Satoshi Yoshida,
  • Sota Sato,
  • Saori Maki-Yonekura,
  • Kiyofumi Takaba,
  • Jungmin Kang,
  • Kensuke Tono,
  • Koji Yonekura and
  • Hiroki Oguri

Beilstein J. Org. Chem. 2025, 21, 226–233, doi:10.3762/bjoc.21.14

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  • hydroamination and temporary protection of nitrile and phenolic hydroxy groups. The synthetic strategy enabled the efficient synthesis of the substructure of saframycins bearing isoquinoline and THIQ units in just four steps from the modular assembly of the three components. We also found the unexpected
  • cyclization to efficiently construct the pentacyclic intermediate 7, as demonstrated in our previous study [15]. Following the pioneering total synthesis of saframycin A (1) by Fukuyama and co-workers taking advantage of the compatibility of phenolic hydroxy groups with PS-type cyclization [22], other groups
  • led by Corey [23], Myers [24][25], Liu [26][27], and Saito [28] also efficiently exploited PS-type reactions to accomplish the total synthesis of saframycin A (1) (Scheme 1b) [3][4][5][29][30][31][32][33][34][35][36][37][38][39][40][41]. However, PS-type reactions impose constraints due to the
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Published 28 Jan 2025

Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide

  • Marios Zingiridis,
  • Danae Papachristodoulou,
  • Despoina Menegaki,
  • Konstantinos G. Froudas and
  • Constantinos G. Neochoritis

Beilstein J. Org. Chem. 2025, 21, 217–225, doi:10.3762/bjoc.21.13

Graphical Abstract
  • convergent chemistry characterized by diversity, complexity and efficiency. MCRs are compatible with C1 chemistry due to the generally great tolerance of different functional groups. They have been mostly employed in the synthesis of oxazolidinones and oxazinanones utilizing CO2 and CO [4][16][17][18][19][20
  • , they are used in a variety of commercially available drugs (Figure 1). Results and Discussion Design and strategy We envisioned applying the Niementowski quinazoline synthesis [25][39][40][41] (Scheme 1A) by employing three different heterocyclic systems as precursors, which have both an orthogonally
  • utilized numerous times in medicinal chemistry campaigns as hits, leads and eventually even drugs, such as 2-aminothiophenes, -quinolines and -indoles [42][43][44][45]. Synthetic exploitation The synthesis of the key cyanoacetamide building blocks was our primary objective. In a parallel setup, a variety
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Published 24 Jan 2025

Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations

  • Seungmin Lee,
  • Minsuk Kim,
  • Hyewon Han and
  • Jongwoo Son

Beilstein J. Org. Chem. 2025, 21, 200–216, doi:10.3762/bjoc.21.12

Graphical Abstract
  • increasing interest as affordable, versatile, and sustainable catalytic systems. These catalysts are extensively employed in organic synthesis owing to their cost-effectiveness, reduced toxicity, and natural abundance [20][21][22][23][24][25][26][27][28]. The use of copper salts has enabled a variety of
  • amidation Recently, Cao and co-workers reported the copper-catalyzed synthesis of 1,2,4-triazole derivatives via an N-acyl nitrene intermediate [76]. As illustrated in Scheme 3, dioxazolones 4 and N-iminoquinolinium ylides 5 served as reactive substrates, leading to the formation of various polycyclic 1,2,4
  • -triazole analogues 6. Both dioxazolones 4 and N-iminoquinolinium ylides 5 demonstrated excellent tolerance in this transformation. Notably, electron-rich dioxazolones exhibited slightly higher reactivity. The proposed catalytic cycle for the copper-catalyzed synthesis of 1,2,4-triazole derivatives is
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Published 22 Jan 2025

Recent advances in electrochemical copper catalysis for modern organic synthesis

  • Yemin Kim and
  • Won Jun Jang

Beilstein J. Org. Chem. 2025, 21, 155–178, doi:10.3762/bjoc.21.9

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  • –heteroatom (C–X, where X = N, O, or halogens) bonds in organic synthesis. Copper was one of the first transition metals employed in cross-coupling to form C–C and C–X bonds [1][2]. In 1901, Ullmann reported the first cross-coupling reaction for the formation of biaryl compounds in the presence of
  • ’ and Fu’s asymmetric C–N bond cross-coupling reactions by merging photoredox catalysis with copper catalysis [29][30]. Building on the success of photoredox catalysis, electrochemistry has emerged as a complementary and attractive strategy for promoting sustainability of organic synthesis. By offering
  • catalysis to organic synthesis, focusing on recent developments in Cu-catalyzed electrochemical reaction categorized into four types: 1) C–H functionalization, 2) olefin addition, 3) decarboxylative functionalization, and 4) coupling reactions (Figure 3). This review aims to provide insight into the
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Published 16 Jan 2025

Nickel-catalyzed cross-coupling of 2-fluorobenzofurans with arylboronic acids via aromatic C–F bond activation

  • Takeshi Fujita,
  • Haruna Yabuki,
  • Ryutaro Morioka,
  • Kohei Fuchibe and
  • Junji Ichikawa

Beilstein J. Org. Chem. 2025, 21, 146–154, doi:10.3762/bjoc.21.8

Graphical Abstract
  • approach to complex molecule synthesis. Despite considerable efforts to develop various catalytic systems, the activation of aromatic C–F bonds often requires high temperatures [1][2][3][4][5][6][7]. Therefore, methods for activating aromatic C–F bonds at ambient temperature remain underdeveloped. We have
  • for the late-stage transformation of C–F bonds, as demonstrated by the orthogonal activation of both aromatic C–F and C–Br bonds, thereby facilitating the synthesis of complex 2-arylbenzofurans. Given that natural and synthetic 2-arylbenzofurans often exhibit considerable biological activities and are
  • , 1255, 1163, 1053, 991, 935, 789, 690 cm–1; HREIMS m/z: [M]+ calcd for C19H14O, 258.1045; found, 258.1035. C–F bond activation through β-fluorine elimination via metalacyclopropanes. Synthesis of 2-arylbenzofurans 3 via the coupling of 1 with 2. Isolated yields are given. aNi(cod)2 (10 mol %), PCy3 (20
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Published 15 Jan 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

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  • Venezian 21, 20133, Milano, Italy 10.3762/bjoc.21.7 Abstract This review reports the achievements in copper(II) triflate-catalyzed processes concerning the multicomponent reactions, applied to the synthesis of acyclic and cyclic compounds. In particular, for the heteropolycyclic systems mechanistic
  • ; heteropolycycles; multicomponent reactions; one-pot reaction; Introduction Copper has gained a relevant role in organic synthesis as an alternative to precious metals due to its low toxicity, ease of handling, high catalytic activity, and cost-effectiveness [1][2]. In recent years, Cu(OTf)2 has significantly
  • transition-metal catalysts provides synthetic tools even more advantageously. Copper has also become very interesting in this field, mainly in processes aimed at synthesizing heterocyclic compounds. Among the various catalysts, Cu(OTf)2 stands out in heterocyclic synthesis and ring transformations due to its
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Published 14 Jan 2025
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