Search results
Search for "synthesis" in Full Text gives 3636 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Microwave-enhanced additive-free C–H amination of benzoxazoles catalysed by supported copper
Beilstein J. Org. Chem. 2025, 21, 1462–1476, doi:10.3762/bjoc.21.108
- synthesis of various benzoxazole derivatives, demonstrating its versatility and practical applicability. Keywords: aerobic oxidation; copper; grafted silica; heterogeneous catalysis; microwave; Introduction 2-Aminoazoles are nitrogenous heterocyclic compounds of high relevance due to their biological and
- , to the best of our knowledge, this study represents one of the few examples of a heterogeneous catalysed copper-mediated C–H amination of benzoxazole. The pursuit for greener methodologies in organic synthesis and transitioning from traditional homogeneous catalysis to the use of heterogeneous
- methods are simple, inexpensive and scalable, making the catalyst reliable and suitable for large scale production. This study aims to optimise an efficient, user-friendly and heterogeneously catalysed procedure that enables the rapid synthesis of 2-aminobenzoxazole derivatives. A key focus is leveraging
Wittig reaction of cyclobisbiphenylenecarbonyl
Beilstein J. Org. Chem. 2025, 21, 1454–1461, doi:10.3762/bjoc.21.107
- depict flattened chemical structures in the reaction schemes. Results and Discussion Synthesis and characterization Methylenetriphenylphosphorane was generated by mixing equimolar amounts of methyltriphenylphosphonium iodide ([MePPh3]I) and sodium tert-butoxide (NaOt-Bu) in THF. The Wittig reaction of
- beneficial for the development of advanced materials. Synthesis and structures of CBBC 1. X-ray crystal structures of (a) 3, (b) 4, and (c) 5 with thermal ellipsoids at 50% probability; all hydrogen atoms are omitted for clarity. VT 1H NMR spectra of 5 in CD2Cl2 at (a) 298 K, (b) 243 K, and (c) 203 K. Blue
Advances in nitrogen-containing helicenes: synthesis, chiroptical properties, and optoelectronic applications
Beilstein J. Org. Chem. 2025, 21, 1422–1453, doi:10.3762/bjoc.21.106
- systems – has granted access to increasingly complex helicene frameworks with well-defined chirality. This review systematically summarizes recent advancements in the synthesis, structural engineering, and chiroptical performance of nitrogen-doped helicenes and their heteroatom-doped derivatives
- – particularly those incorporating additional heteroatoms within the helical π-conjugated framework – remains lacking. This review addresses this gap by systematically summarizing recent advances (from the past five years) in the synthesis, structural modification, and chiroptical properties of nitrogen-doped
- azahelicenes represent a particularly significant subclass due to their extended π-conjugation and potential for enhanced chiroptical properties. Over the past few years, multiple research groups have investigated their synthesis, structural characteristics, and optoelectronic behavior. Notably, in 2021, Jux
Tautomerism and switching in 7-hydroxy-8-(azophenyl)quinoline and similar compounds
Beilstein J. Org. Chem. 2025, 21, 1404–1421, doi:10.3762/bjoc.21.105
- , printing, and coloring agents for various materials, due to their excellent color fastness, high stability, and ease of synthesis. The azo functionality allows for a wide range of colors to be achieved by altering the substituents on the azo group, improving the color intensity, lightfastness, and wash
- substitution in 7-OH quinoline, where the most of the requirements for clean switching are achieved if the K tautomer is considered as off-state and the E one as on-state. Experimental Synthesis and structure elucidation Materials The starting reagents and solvents were purchased from Sigma-Aldrich and
- Fluorochem and used as received. The solvents used for the experimental synthesis (HPLC grade) were purchased from Sigma-Aldrich. All other materials were commercial products of analytical grade and used as supplied. Analytical TLC (thin-layer chromatography) was performed on Merck silica gel 60 F254
Reactions of acryl thioamides with iminoiodinanes as a one-step synthesis of N-sulfonyl-2,3-dihydro-1,2-thiazoles
Beilstein J. Org. Chem. 2025, 21, 1397–1403, doi:10.3762/bjoc.21.104
- Bukireva str., Perm 614990, Russia Department of Organic & Biomolecular Chemistry, Ural Federal University, 19 Mira str., Yekaterinburg 620002, Russia Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences, 22/20 S. Kovalevskoy str., Yekaterinburg 620108, Russia Sustainable
- iminoiodinanes. A library of 31 examples of tetrasubstituted 1,2-thiazoles was thus synthesized in high yields. The effectiveness of the synthesis method for these poorly studied 1,2-thiazoles was confirmed by scaling the reaction using gram amounts of the starting thioamide. Keywords: iminoiodinanes; sulfonyl
- groups; synthesis; 1,2-thiazolines; thioamides; Introduction 1,2-Thiazoles (isothiazoles) exhibit a wide range of biological activity (Figure 1): antipoliovirus [1], anticancer [2][3][4][5][6][7], against Parkinson's disease [8], and diabetes [9][10][11], and are also used as microbiocides [12][13
High-pressure activation for the solvent- and catalyst-free syntheses of heterocycles, pharmaceuticals and esters
Beilstein J. Org. Chem. 2025, 21, 1374–1387, doi:10.3762/bjoc.21.102
- -products. A computational study accompanies the experimental data to interpret the outcome of the reactions. Keywords: acetaminophen; acetylsalicylic acid; benzimidazoles; catalyst-free synthesis; cyclization; esters; high hydrostatic pressure; pyrazoles; Introduction Non-traditional activation methods
- are one of the major driving forces in green synthesis [1][2]. High hydrostatic pressure (HHP) activation, one of such methods, is based on mechanical compression force. The typical pressure range is 2–20 kbar that is orders of magnitude greater than the conditions traditionally employed in chemistry
- with pressurized gases (0.01–0.1 kbar). The first reports of using HHP were related to food industry applications [3][4], and later in chemical synthesis [5][6]. While the technique had been known since the late 1800s, and it had become popular in materials science and inorganic synthesis, it has
Oxetanes: formation, reactivity and total syntheses of natural products
Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101
- chemistry; natural products; oxetane; reactivity; synthesis; Introduction Oxetanes are 4-membered heterocyclic compounds containing one oxygen atom whose discovery dates back to the 1870s when the first synthesis of the parent, unsubstituted oxetane was reported by Reboul [1]. Over the next 100 years, it
- E [30] and daphnepapytone C [31] from the 2020s (Figure 4). Most of these compounds possess intriguing biological activities and selected examples from this list are discussed in more detail in chapter 4 with regards to their isolation, bioactivity and a recent total synthesis. The aim of this work
- of selected oxetane-containing natural products with a focus on the most critical and strategic bond formations. Review 1 Construction of the 4-membered ring One of the two principal approaches towards the synthesis of oxetanes is constructing the 4-membered ring de novo. This can be further
Recent advances in amidyl radical-mediated photocatalytic direct intermolecular hydrogen atom transfer
Beilstein J. Org. Chem. 2025, 21, 1306–1323, doi:10.3762/bjoc.21.100
- demonstrated a decent methodology of organic synthesis. These elegant strategies presented powerful C–H bond transformation toolkits (Figure 1b) [6][7][8]. One of the exceptions to the perfection is the pre-functionalization of substrates. Current catalytic methodologies predominantly rely on substrate
- (Figure 1c) [19][20][21][22][23][24][25][26][27], serve as key species for the HAT process. These HR were generated from different HAT reagent precursors (HRP) in a variety of strategies. Among these, amidyl radical HRPs have gained significant attention in recent years due to their ease of HRP synthesis
- and the relatively green chemistry of generating amidyl radicals. Amidyl radicals offer several advantages that enhance their applicability in organic synthesis: 1) The BDE of amidyl N–H bond is more than 105 kcal/mol, relative to the bond (C–H, Si–H, B–H, and Ge–H) which BDE is lower than 100 kcal
Recent advances and future challenges in the bottom-up synthesis of azulene-embedded nanographenes
Beilstein J. Org. Chem. 2025, 21, 1272–1305, doi:10.3762/bjoc.21.99
- Bartlomiej Pigulski Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383 Wrocław, Poland 10.3762/bjoc.21.99 Abstract In recent years, significant progress has been made in the synthesis of various nanographenes incorporating non-benzenoid rings, expanding the scope of molecular
- has sparked a continuously growing interest in synthesis of new carbon-rich unsaturated molecules and materials [1]. Graphene is a revolutionary material with exceptional properties, driving advancements across various scientific, industrial, and technological fields like organic electronics [2
- crucial for fine-tuning their properties. An alternative is the bottom-up approach where various nanographenes are synthesized form smaller building blocks via classical organic synthesis. This strategy enables precise control over the structure and topology, leading to the development of a vast array of
Recent advances in oxidative radical difunctionalization of N-arylacrylamides enabled by carbon radical reagents
Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98
- been extensively investigated by researchers. Keywords: carbon radical reagents; intramolecular transformations; N-arylacrylamides; oxidative difunctionalization; radical reactions; Introduction Alkenes, as abundant and versatile feedstocks, have been widely employed in organic synthesis
- heteroatom for the synthesis of functionalized oxindoles was also reported in 2013 [3]. In this study, DBU was employed as a ligand and TBHP as an oxidant. A series of ethers, including 1,2-dimethoxyethane, THF, 1,4-dioxane, tetrahydro-2H-pyran, 2,3-dihydrobenzofuran, tetrahydro-2H-thiopyran, and N
- oxidant and initiator, enabling an efficient intermolecular cascade cyclization process (Scheme 5) [5]. In this strategy, a novel, selective, metal-free synthetic method was introduced for the synthesis of isoxazoline-featured oxindoles through iminoxyl radical-promoted cascade oxyalkylation
Optimized synthesis of aroyl-S,N-ketene acetals by omission of solubilizing alcohol cosolvents
Beilstein J. Org. Chem. 2025, 21, 1201–1206, doi:10.3762/bjoc.21.97
- -N-benzylbenzothiazolium salts in 1,4-dioxane at room temperature in short reaction time in 20–99% yield. This protocol represents a considerable improvement over the standard synthesis in 1,4-dioxane/ethanol mixtures at elevated temperatures. Keywords: aroyl chlorides; aroyl-S,N-ketene acetals
- deprotonation, followed by chloride elimination/neutralization from the zwitterionic tetrahedral intermediate 5 to give the target molecule 1. The standard protocol for the synthesis of (hetero)aroyl-S,N-ketene acetals 8 from (hetero)aroyl chlorides 6 and 2-methylbenzothiazolium salts 7 employs a twofold excess
- examples), the average yield of 57% indicates that the process might require optimization, in particular, for further methodological implementation. Here, we report on the improved synthesis of (hetero)aroyl-S,N-ketene acetals 8 by careful solvent and temperature optimization. Results and Discussion The
Synthesis of β-ketophosphonates through aerobic copper(II)-mediated phosphorylation of enol acetates
Beilstein J. Org. Chem. 2025, 21, 1192–1200, doi:10.3762/bjoc.21.96
- [1][2][3][4][5] due to the numerous applications of phosphorus-containing compounds in pharmaceuticals, biology, agrochemistry, organic synthesis, and materials science [6][7][8][9][10][11][12][13]. Among various organophosphorus compounds, β-ketophosphonates have received particular attention for
- various synthetically useful transformations, including alkene synthesis via Horner–Wadsworth–Emmons reaction [14][15], heterocycle construction [16][17], and the synthesis of chiral β-amino and β-hydroxy phosphonic acids [18][19]. Furthermore, they exhibit metal-complexing abilities [20], and anti
- tolerance and can be applied for the gram-scale synthesis of target compounds. Conducted mechanistic studies revealed that the discovered transformation proceeds via the formation of P-centered radicals produced by the oxidation of the corresponding phosphorous precursors by copper(II)-containing species
Selective monoformylation of naphthalene-fused propellanes for methylene-alternating copolymers
Beilstein J. Org. Chem. 2025, 21, 1183–1191, doi:10.3762/bjoc.21.95
- well with the observed reactivities and selectivity. Attempted macrocyclization leading to linear polymers Formyl groups have diverse reactivities and enable facile condensation, dynamic covalent chemistry, and so on. In this work, we tried the synthesis of cyclic oligomers composed of naphthalene
- electrophilic functionalization. a) Synthesis of methylene-alternating copolymers of fully π-fused propellanes. DCE, 1,2-dichloroethane. b) 1H NMR (500 MHz, top) and 13C (126 MHz, bottom) NMR spectra of [4.3.3]_CH2OH and [4.3.3]_linear in CDCl3 at room temperature. Gas adsorption (filled circles) and desorption
Enhancing chemical synthesis planning: automated quantum mechanics-based regioselectivity prediction for C–H activation with directing groups
Beilstein J. Org. Chem. 2025, 21, 1171–1182, doi:10.3762/bjoc.21.94
- Julius Seumer Nicolai Ree Jan H. Jensen Department of Chemistry, University of Copenhagen, Copenhagen, Denmark 10.3762/bjoc.21.94 Abstract The mild and selective functionalization of carbon–hydrogen (C–H) bonds remains a pivotal challenge in organic synthesis, crucial for developing complex
- reliable regioselectivity predictions that are essential for accelerating innovation in materials science and medicinal chemistry. Keywords: C–H activation; chemical synthesis planning; directing groups; quantum mechanics; regioselectivity prediction; Introduction The activation and functionalization of
- bonds in organic chemicals. Therefore, their selective functionalization is essential for advancing the synthesis of complex molecules like pharmaceuticals, polymers, or agrochemicals [1][2][3]. Advancements in organometallic catalysis have facilitated significant progress in this area through C–H
Correction: Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates
Beilstein J. Org. Chem. 2025, 21, 1170–1170, doi:10.3762/bjoc.21.93
- Deepa Nair Abhishek Tiwari Banamali Laha Lakshminarayana Satham Irishi N. N. Namboothiri Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400 076, India 10.3762/bjoc.21.93 Keywords: arylidenemalonates; curcumins; cyclohexanones; diastereoselective synthesis; Michael
A multicomponent reaction-initiated synthesis of imidazopyridine-fused isoquinolinones
Beilstein J. Org. Chem. 2025, 21, 1161–1169, doi:10.3762/bjoc.21.92
- (IMDA), and dehydrative re-aromatization reactions for the synthesis of imidazopyridine-fused isoquinolinones is developed. Gaussian computation analysis on the effect of the substitution groups for the IMDA reaction is performed to understand the reaction mechanism. Keywords: Groebke–Blackburn
- in 89–98% yields. Reactions of 4 with acryloyl chloride (5, 1.5 equiv) in the presence of Et3N (2 equiv) at room temperature in anhydrous CH2Cl2 for 6 h afforded 19 N-acylated compounds 6 in 80–90% yields [19]. With N-acylated GBB adducts 6 in hand, the synthesis of imidazopyridine-fused
- , Supporting Information File 1), but it was not stable enough for isolation. The structure of 8a was confirmed by single crystal X-ray diffraction analysis. The optimized reaction conditions were used to evaluate the substrate scope of the synthesis of imidazopyridine-fused isoquinolinones 8 (Scheme 3). The
Synthetic approach to borrelidin fragments: focus on key intermediates
Beilstein J. Org. Chem. 2025, 21, 1135–1160, doi:10.3762/bjoc.21.91
- architecture. Although extensive research has explored its pharmacological properties and various synthetic approaches, significant challenges remain in the efficient synthesis of borrelidin and its analogs. Existing literature largely focuses on total synthesis, bioactivity, and structural modifications
- , leaving a notable gap in fragment-focused synthesis, particularly for its intricate substructures. This review seeks to address this gap by offering a detailed examination of borrelidin fragment synthesis, highlighting key challenges and innovative strategies involved. By pinpointing unresolved synthetic
- hurdles, this work advocates for a fragment-focused approach as a crucial step toward advancing borrelidin research and expanding its potential applications. Keywords: borrelidin analogs; borrelidin derivatives; borrelidin fragments; borrelidin synthesis; fragment-based synthesis; Introduction
Investigations of amination reactions on an antimalarial 1,2,4-triazolo[4,3-a]pyrazine scaffold
Beilstein J. Org. Chem. 2025, 21, 1126–1134, doi:10.3762/bjoc.21.90
- -chlorophenyl)-[1,2,4]triazolo[4,3-a]pyrazine were synthesised, purified (≥95% purity, determined by 1H and 13C NMR and HPLC–MS analysis) and assayed for in vitro antimalarial activity. Results and Discussion Synthesis of aminated triazolopyrazine analogues The amination of 5-chloro-3-(4-chlorophenyl)-[1,2,4
- with relevant position numbering. Crystals obtained for 2 were analysed by X-ray crystallographic studies and confirmed the NMR-based structure assignment. The crystal structure of 2 is shown as a thermal ellipsoid plot below (Figure 3). With a simplified approach for the synthesis of aminated
- triazolopyrazines from 5-halogen substituted triazolopyrazines and primary amines now in hand, 13 other commercially available liquid primary amines were employed for the synthesis of additional aminated triazolopyrazine analogues (Scheme 2). TLC analysis of the room temperature reaction with phenethylamine (as
Gold extraction at the molecular level using α- and β-cyclodextrins
Beilstein J. Org. Chem. 2025, 21, 1116–1125, doi:10.3762/bjoc.21.89
- used to wash the gold precipitate by using the anti-solvent acetone. Thiolated β-CD derivative for selective gold precipitation Fang et al. reported the synthesis and application of a 6-thiolated β-CD derivative (with unspecified degree of substitution) to precipitate metallic gold from strongly acidic
A versatile route towards 6-arylpipecolic acids
Beilstein J. Org. Chem. 2025, 21, 1104–1115, doi:10.3762/bjoc.21.88
- important role as building blocks for peptide synthesis [1][2][3][4][5], as organocatalysts [6][7][8][9][10] and as enzyme inhibitors [4][11][12][13]. The incorporation of such amino acids into peptides can, for example, influence peptide conformation, the binding affinity to receptors [14], as well as
Supramolecular assembly of hypervalent iodine macrocycles and alkali metals
Beilstein J. Org. Chem. 2025, 21, 1095–1103, doi:10.3762/bjoc.21.87
- dynamic assembly and disassembly. Our previous study [18] demonstrates the synthesis of various HIM variants, including a new phenylalanine-based HIM, which show the dynamic behavior of HIM assemblies in solution via addition and removal of anions (Figure 1A). Moreover, due to secondary bonding in the HIM
- . Results and Discussion We have reported the synthesis of several variations of valine and phenylalanine-based HIMs that are based on benzene-, naphthalene-, and anthraquinone systems [18][19]. This study employed a phenylalanine and iodobenzoic acid-based HIM system owing to its simplicity in synthesis
Salen–scandium(III) complex-catalyzed asymmetric (3 + 2) annulation of aziridines and aldehydes
Beilstein J. Org. Chem. 2025, 21, 1087–1094, doi:10.3762/bjoc.21.86
- -containing five-membered saturated heterocycles. They are not only useful building blocks for the synthesis of biologically active compounds [1], for example, side-chain precursor of paclitaxel [2], but also widely exist in some pharmaceuticals [3][4], such as antibacterial agents of Gram-positive organisms
- alcohols and aldehydes [11] and through [2 + 3] cycloaddition of azomethine ylides and carbonyl dipolarophiles [12]. Recently, the [2 + 3] annulation of aldehydes and donor–acceptor dialkyl 2-aryl-1-sulfonylaziridine-2,2-dicarboxylates, which generate azomethine ylides, has been developed for the synthesis
- require dineopentyl aziridine-2,2-dicarboxylates to realize high enantioselectivity, while the synthesis of the chiral ligand N,N'-dioxide requires multiple steps. Herein, we present a convenient highly diastereo- and enantioselective synthesis of dialkyl 2,5-diaryl-1-sulfonyloxazolidine-2,2
Recent advances in synthetic approaches for bioactive cinnamic acid derivatives
Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85
- significantly to the efficient and cost-effective production of cinnamic acid derivatives. This review focuses on diverse, one-step strategies to access cinnamic acid derivatives with more efficient, highly selective, and sustainable approaches. By examining recent advancements in the design and synthesis of
- mechanochemistry synthesis of cinnamic acid derivatives. Herein, Kulkarni and Atapalkar (2023) converted cinnamic acids into the corresponding amides 17 and 18 and hydrazide 19 in moderate yields (Scheme 6) [30]. Impressively, the reaction capacity could be increased to produce 100 g of the amide products with 90
- % yields. Müller and co-workers (2019) reported the synthesis of 6-amino-5-carboxamidouracil derivatives 20 and 21, precursors for A2A antagonists, in good yields by using non-hazardous (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino(morpholino)carbenium hexafluorophosphate (COMU) as the coupling
Biobased carbon dots as photoreductants – an investigation by using triarylsulfonium salts
Beilstein J. Org. Chem. 2025, 21, 1024–1030, doi:10.3762/bjoc.21.84
- , organosilanes). The latter strategy is the most prevalent one, due to the simplicity of the procedures, environmental friendliness, and equipment required, as well as the ability to use a large variety of precursors. In the bottom-up synthesis methods, conversion of the carbon precursors is obtained by having
- photooxidant or photoreductant in the presence of a suitable electron donor or acceptor [18], and these properties have been exploited in procedures for the formation of both C–C and C–heteroatom bonds [18][19]. Our research groups recently focused on the application of CDs in light-mediated organic synthesis
- have been considered as a promising source of aryl radicals and employed in organic synthesis [20][21][22][23][26][27][28][29][30][31][32]. This investigation aims to compare the performance of CDs prepared from several carbon precursors including citric acid, glucose, and organic waste materials via
Pd-Catalyzed asymmetric allylic amination with isatin using a P,olefin-type chiral ligand with C–N bond axial chirality
Beilstein J. Org. Chem. 2025, 21, 1018–1023, doi:10.3762/bjoc.21.83
- Isatin is a well-known natural indole derivative. Due to the broad biological activities of its derivatives, extensive research has been conducted on their synthesis. Furthermore, the isatin framework is a versatile starting material for various transformations, including multicomponent reactions and the
- synthesis of spirocyclic compounds [1][2][3]. The nucleophilicity of isatin at the nitrogen atom allows it to participate in reactions such as alkylation [4], arylation [5], and aza-Michael addition [6][7][8]. However, the products obtained from these reactions are primarily achiral or racemic, and only a
Other Beilstein-Institut Open Science Activities
