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Search for "derivatives" in Full Text gives 2809 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Azide–alkyne cycloaddition (click) reaction in biomass-derived solvent CyreneTM under one-pot conditions
Beilstein J. Org. Chem. 2025, 21, 1544–1551, doi:10.3762/bjoc.21.117
- -dioxane) or low (DMF, NMP, DMSO) (Figure 1). While low conversion was still detected in biomass-originated 2-MeTHF, MeLev, and EtLev established better performance. When their corresponding 4-alkoxy derivatives were applied, moderate (Me-4MeOV) or slightly lower (Et-4EtOV) conversions could be observed
- 1,2,3-triazole derivatives were generally obtained with good to excellent yields (50–96%). Both electron-withdrawing (fluoro (3b) or trifluoromethyl (3c)) and electron-donating (methoxy, phenoxy, and alkyl (3d–h)) groups were tolerated on the acetylene reaction partner species. In accordance with
- -triazoles in CyreneTM (Figure 4). It was shown that the protocol resulted in the formation of products 3a and 5b–f with yields of 57–91% depending on the structure of the bromide derivatives. The isolated yields were in the same range as reported by Citarella et al. [39]. The presence of a terminal carbon
General method for the synthesis of enaminones via photocatalysis
Beilstein J. Org. Chem. 2025, 21, 1535–1543, doi:10.3762/bjoc.21.116
- intermediates in the synthesis of several derivatives with important applications in medicinal chemistry. Furthermore, many marketed drugs feature the enaminone structural moiety. In this context, we have developed a photoredox and nickel catalytic system to rapidly forge the enaminone scaffold from 3
- -bromochromones via a Michael reaction of an amine with an electron-deficient alkene moiety and subsequent photocatalyzed debromination. With this dual catalytic system, a range of structurally diverse enaminone derivatives have been achieved in good yields with total trans selectivity. Mechanistic studies
- electrophilicity of the β-carbon due to the electron-donating nature of the methyl group. Subsequently, we turned our attention to investigate a range of amine derivatives 8 under the standard conditions. When morpholine was replaced by piperidine, the expected enaminone 9g was provided, albeit in lower yield
Ambident reactivity of enolizable 5-mercapto-1H-tetrazoles in trapping reactions with in situ-generated thiocarbonyl S-methanides derived from sterically crowded cycloaliphatic thioketones
Beilstein J. Org. Chem. 2025, 21, 1508–1519, doi:10.3762/bjoc.21.113
- chemoselectivity was observed in reactions of 1a with 5-mercaptotetrazole 4b. However, due to a lower reactivity observed for 4c,d towards 1a, the experiments with these derivatives were unsuccessful and formation of undesired side products was observed in both cases. Unexpectedly, a different chemoselectivity was
- cyclobutanone derivatives 1b, 1c and 1d suggest that the type of the spiro-substituent may play an important role in the rearrangement process. Whereas thioaminals 9 obtained in reactions with 1b and 1d tend to easily undergo the rearrangement leading to the corresponding dithioacetals 10, the analogous process
- polymer chemistry [36] and the crop protection industry [37] as well. Therefore, in extension of a typically synthetic work, a preliminary study on biological activity of the hitherto unreported 1H-tetrazole derivatives such as thioaminals 9 and dithioacetals 10 was carried out and it demonstrated that
Highly distinguishable isomeric states of a tripodal arylazopyrazole derivative on graphite through electron/hole-induced switching at ambient conditions
Beilstein J. Org. Chem. 2025, 21, 1496–1507, doi:10.3762/bjoc.21.112
- derivatives play a crucial role in realizing efficient bidirectional photoswitches with longer half-lives [18][19]. In particular, replacing one of the phenyl units in AB with a five-membered heterocycle and the resulting Z isomer of phenylazoheteroarenes has extended half-life ranging up to 1000 days and
- hydrogelator [25], photoregulation of DNA nanosystems [26], in controlling surface wettability [27], and in solar energy conversion [28]. Considering these advantages, we synthesized C3 symmetric tripodal azopyrazole-based derivatives having a trimesoyl core and aroylazole connections as a solid-state
- changes abruptly. In other words, the abrupt change in current is caused by isomerization or geometrical changes in the molecule. The change in tunneling current has been earlier used to identify geometrical changes/isomerization of spin-cross-over molecule [7] and azobenzene derivatives [10][11][12][15
Heterologous biosynthesis of cotylenol and concise synthesis of fusicoccane diterpenoids
Beilstein J. Org. Chem. 2025, 21, 1489–1495, doi:10.3762/bjoc.21.111
- with limited chemical transformations is highly desirable and should enable the discovery of new fusicoccane derivatives with improved biological activity. Inspired by the biosynthetic machinery of terpenoids, we have reported a hybrid synthetic strategy for accessing bioactive terpenoids by combining
Photoredox-catalyzed arylation of isonitriles by diaryliodonium salts towards benzamides
Beilstein J. Org. Chem. 2025, 21, 1480–1488, doi:10.3762/bjoc.21.110
- significant attention within organic and medicinal chemistry. Commonly, amide bonds are formed via the reaction of carboxylic acids or their derivatives with appropriate amines (Scheme 1A) [4]. Although this conventional approach is effective and straightforward, it usually suffers from harsh conditions and
Copper catalysis: a constantly evolving field
Beilstein J. Org. Chem. 2025, 21, 1477–1479, doi:10.3762/bjoc.21.109
- straightforward workup and minimized free copper on solution. Due to this, the catalyst could be regenerated and reused in up to eight cycles. Upon optimization, this practical and versatile method could be used for the synthesis of several benzoxazole derivatives. A Letter was contributed by D’Andrea and Jademyr
- process of 4,4-dichloro-2-butenoic acid derivatives and bis(pinacolato)diboron is described [10]. The transformations feature excellent chemo-, regio-, and diastereoselectivities, and the resulting products are highly functionalized. Due to this, they were considered as versatile building blocks for the
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
- 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
- determine the percentage composition of starting material and products 2a, 2a-o and 2a-o-hydrol. The reaction was perfectly reproducible and no other derivatives were observed. As shown in Figure 1b, when the reaction was conducted without a catalyst, only ring opening was observed, accounting for 47%. By
Wittig reaction of cyclobisbiphenylenecarbonyl
Beilstein J. Org. Chem. 2025, 21, 1454–1461, doi:10.3762/bjoc.21.107
- peripherally modified CBBC derivatives have also been prepared and were shown to have fascinating properties [17][18][19][20][21]. For example, carbazole-substituted donor–acceptor-type CBBC derivatives exhibit both efficient circularly polarized luminescence (CPL) and thermally activated delayed fluorescence
- internally functionalized DBC derivatives [22]. The dihedral angle between the mean planes of the two terminal benzene units is 83°, which is comparable to those of other derivatives. Next, products 3 and 5 were analyzed by variable temperature (VT) 1H NMR spectroscopy. The 1H NMR spectrum of bis-olefin 5 in
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
- [33] and Ishigaki’s [34] groups independently reported a class of highly twisted nitrogen-doped heptalene derivatives (e.g., compound 20a), which exhibit consistent absorption at 315 nm and blue fluorescence centered near 450 nm, regardless of the substituents. These compounds display redox and
- , Tanaka’s group synthesized benzannulated double aza[9]helicene 32a and its alkylated derivatives 32b and 32c via a one-pot oxidative fusion strategy [46]. Compared to the parent compound 32a (ΦF = 0.07), compounds 32b and 32c exhibit significantly enhanced ΦF (0.35), red-shifted absorption bands, and |gabs
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
- ESIPT exists along with the cis/trans isomerization, creating a rather complicated interplay between two competitive processes. Experimental [49][75][76][77][78][79][80] and theoretical [81][82][83][84] studies of compound 3 and derivatives clearly indicate the excited-state competition between the
- and excited state) were optimized without restrictions, using tight optimization criteria and an ultrafine grid in the computation of two-electron integrals and their derivatives. The true minima were verified by performing frequency calculations in the corresponding environment. The implicit
N-Salicyl-amino acid derivatives with antiparasitic activity from Pseudomonas sp. UIAU-6B
Beilstein J. Org. Chem. 2025, 21, 1388–1396, doi:10.3762/bjoc.21.103
- human system. In this study, we isolated two previously undescribed N-salicyl-amino acids as natural products (1 and 2) and other two new derivatives (3 and 4) from the organic extract of a culture broth in a modified starch–glucose–glycerol (SGG) medium of Pseudomonas sp. UIAU-6B. The structure of the
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
- protocol was even applied in the elegant syntheses of platencin [30], and steroid derivatives [31]. Despite these encouraging applications, there is a broad area to be developed for the advancement of green synthesis efforts. Continuing our program on developing environmentally benign synthetic methods [32
Oxetanes: formation, reactivity and total syntheses of natural products
Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101
- epoxides and heteroatom-stabilised carbocations generated from alkenes (Scheme 10). In 1992, Arjona and co-workers examined the synthesis of 4,7-dioxatricyclo[3.2.1.03,6]octane derivatives 45 via intramolecular cyclisation of the corresponding hydroxyalkene precursors 44 using arylsulphenyl and arylselenyl
- electrophilicity of the carbonyl [74]. The oxetane products were obtained in good to high yields and further transformed into useful sulphone, butenolide and tetrahydrofuran derivatives. Besides laboratory-scale reactions, this ring expansion has also found applications in industry, specifically for a multi
- approach to these derivatives can proceed through functionalisations of readily available oxetane-containing building blocks. The most versatile precursor of these building blocks is 3-oxetanone (133) which was first recognised by Carreira and colleagues (Scheme 34). Besides describing its possible
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
- formation of two tropylium fragments within a single molecule. Additionally, they exhibit typical azulene-like optical absorption and the aromatic properties characteristic of azulene subunits. Liu and co-workers extended this chemistry to substituted naphthalene derivatives which led to chrysene fused with
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
- –g), further demonstrating the method’s versatility. Furthermore, a range of isocyanide derivatives, encompassing primary, secondary, and tertiary aliphatic isocyanides, demonstrated compatibility by producing the desired oxindoles 19h–j with moderate to good yields. To investigate the reaction
- radical then reacts with acrylamide to yield the desired product 37. As shown in Scheme 21, a visible light-induced trifluoromethylation/arylation using Umemoto’s reagent for the synthesis of trifluoromethylated oxindole derivatives was reported by Huang and Zhang’s group in 2021 [13]. This method is
- %. Heteroaryl and aliphatic sulfoxonium ylides also participated in the reaction, though with slightly lower yields of product 76f–h. Furthermore, the scope was extended to other N-arylacrylamide derivatives, affording products 76i and 76j with yields of 50% and 90%, respectively. As shown in Scheme 36, the
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
- ; condensation; Einhorn-type acylation; 2-methyl N-benzyl benzothiazolium salts; Introduction Aroyl-S,N-ketene acetals, in particular N-benzyl derivatives 1, are very short donor–acceptor chromophores that have recently found a renaissance due to their peculiar intense solid-state emission and significant turn
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
- substitution pattern in the aryl ring does not have a significant effect on the yield of 3 for both acceptor and donor derivatives, which shows the versatility of the developed protocol. However, among halogen-containing derivatives, higher yields were observed for bromine-substituted ones (products 3i and 3l
Synthetic approach to borrelidin fragments: focus on key intermediates
Beilstein J. Org. Chem. 2025, 21, 1135–1160, doi:10.3762/bjoc.21.91
- 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
- a marine or hypersaline environment natural products library to identify potent drugs, a putatively novel metabolite co-produced with borrelidin was discovered, expanding the potential for new borrelidin derivatives. This led to the formation of the so-called “borrelidin family” (Table 1), with
- derivatives named alphabetically starting from the original borrelidin 1, designated as borrelidin A (Table 1, entry 1). A rare nitrile moiety at C12 of the macrolide ring in borrelidin A is present in most members of the borrelidin family (Table 1, entries 4, 5, 7–11, 13–16, and 18), except for borrelidin B
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
- (MMV) [3]. OSM’s aim is to “find a drug for malaria as quickly as possible” [3]. In the past, OSM synthesised and screened various derivatives of three related parent scaffolds (series 1–3) provided by GlaxoSmithKline (GSK) in non-commercial antimalarial screening datasets [4]. The group’s current
- ]pyrazine (hereafter referred to as “triazolopyrazine”) analogues, including derivatives inherited from Pfizer and newly synthesised analogues [5]. Triazolopyrazine compounds of OSM series 4 are believed to dysregulate P. falciparum ATP4ase (PfATP4), possibly as a direct inhibitor [5]. Series 4 compounds
- good yield with this straightforward methodology (and without the need for toluene reflux), and to determine the distribution of products obtained for this synthetic approach, by exhaustive analysis of reaction mixtures by HPLC, MS and NMR. Ultimately, 14 aminated derivatives of 5-chloro-3-(4
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
- , thus confirming a strong interaction affinity lying within the 104 molar range. Gold extraction with β-CD and derivatives The possibility of using β-CD instead of α-CD in gold recovery and extraction is highly sought after by both researchers and industry because of the readiness of availability of β
A versatile route towards 6-arylpipecolic acids
Beilstein J. Org. Chem. 2025, 21, 1104–1115, doi:10.3762/bjoc.21.88
- . It contains a six-membered ring and is, like its five-membered correlate, known for its secondary structure inducing properties, which are particularly useful in the design of peptide conformations. We present a new and improved way to generate enantiomerically pure pipecolic acid derivatives with
- -inducing properties in peptides [22][23][24]. Furthermore, derivatives of pipecolic acid are known for their bioactivity as secondary metabolites [25][26][27] and for being building blocks for piperidine alkaloids [28] with a variety of uses. Results and Discussion Addressing specific positions in the ring
- a key intermediate product. This late-stage approach was previously described by us while utilising Suzuki–Miyaura or Sonogashira–Hagihara cross-coupling reactions to generate pipecolic acid derivatives with alkynyl substituents in the C6 position [35]. Here, we present a robust synthetic route to
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
- moieties of biologically active compounds. A salen–scandium triflate complex-catalyzed asymmetric (3 + 2) annulation of dialkyl 1-sulfonylaziridine-2,2-dicarboxylates and aldehydes generated optically active functionalized oxazolidine derivatives in moderate to good yields and good to excellent
- enantioselectivities and high diastereoselectivities. A reasonable reaction mechanism was proposed and rationalized the experimental results. Keywords: aldehyde; annulation; aziridine; oxazolidine; ring expansion; scandium triflate; Introduction Oxazolidine derivatives are an important class of nitrogen and oxygen
- [5] and the FDA-approved antibiotic linezolid [6] (Figure 1). Both chiral oxazolidines [7][8] and oxazolidinones [9][10] have been utilized as chiral auxiliary groups in many asymmetric organic transformations. Oxazolidine derivatives have been prepared mainly from condensation of vicinal amino
Recent advances in synthetic approaches for bioactive cinnamic acid derivatives
Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85
- Cinnamic acid derivatives represent a significant class of biologically active compounds exhibiting a broad spectrum of activities, such as antifungal, antidengue, antimetastatic, antimicrobial, antibacterial, and anticancer properties. Their preparation has attracted considerable attention due to their
- versatile applications across the pharmaceutical, food, and chemical sectors. This review elucidates the functional groups of cinnamic acid that are instrumental in the rational design of biologically active derivatives. A comprehensive representative of recent advancements in synthetic methodologies over
- the past five years is presented, particularly emphasizing the active scaffolds of bioactive cinnamic acid derivatives. The review provides a strategic overview of alternative synthetic routes and highlights the latest innovations, including more efficient, highly selective, and environmentally
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
- photoreductants, and we considered triarylsulfonium salts Ar3S+X− as suitable probes. Such derivatives are photoreactive molecules characterized by a positively charged sulfur atom bonded to three aromatic moieties [20][21][22][23], mainly employed as photoacid generators in cationic polymerization [19]. Apart
- (whose EREDonset value were in the range −1.60 and −1.92 V vs Ag/AgCl, a set comparable to that reported in the literature for fac-Ir(ppy) [37], which was effectively used in the photoredox-catalyzed reduction of sulfonium salts [29]) and derivatives 1a–d (EAr3S+/Ar3S• = −1.35 to −1.46 V vs Ag/AgCl; see
- + species, a process where transition-metal-based complexes are employed [29], often (in the case of Ru(II)-based derivatives) in the presence of tertiary amines as sacrificial reductants [27][28]. Nonetheless, while this work serves primarily as a preliminary study comparing the reducing power of various
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