Search results
Search for "derivatives" in Full Text gives 2800 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Chitosan-supported CuI-catalyzed cascade reaction of 2-halobenzoic acids and amidines for the synthesis of quinazolinones
Beilstein J. Org. Chem. 2025, 21, 839–844, doi:10.3762/bjoc.21.67
- group, we investigated the reactions with various substituted 2-halobenzoic acids. The reactivity of 2-iodobenzoic acid derivatives (3a–d, 90−96% yields) was higher than that of 2-bromobenzoic acid derivatives (3a–d, 57−73% yields), the electronic properties of the substituents on the benzene ring had
- investigated the reactions of different 2-halobenzoic acid derivatives with amidines where R2 was a tert-butyl group. The results showed that 2-bromobenzoic acid derivatives (3j–k, 55−65% yields) displayed lower activity compared to 2-iodobenzoic acid derivatives (3i–l, 73−90% yields), with a decrease in
- reaction activity observed when substituents were presented on the benzene ring. Finally, we examined reactions with 2-halobenzoic acid derivatives where the R2 substituent was a phenyl group. In this case, the reactivity of 2-iodobenzoic acid derivatives (3m–p, 61–99% yields) was again superior to that of
Substituent effects in N-acetylated phenylazopyrazole photoswitches
Beilstein J. Org. Chem. 2025, 21, 830–838, doi:10.3762/bjoc.21.66
- examples. Azobenzene and its derivatives show two characteristic absorption bands, namely a π→π* transition around 330 nm and an n→π* one around 450 nm, respectively [22]. The molecule can populate the thermodynamically metastable Z isomer by addressing these transitions in the thermally stable E form. The
- relative position of the absorption bands in the azobenzene derivatives depends on the substitution pattern on the aromatic rings, which can act as a handle to affect the absorption properties of the compound class [3]. For instance, push–pull systems or the introduction of tetra-ortho substituents were
- reported to either bathochromically shift the UV–vis absorption spectrum or lead to a better separation of the n→π* bands of the two photoisomers and allow for visible-light-responsive switches [23][24][25][26]. In recent years, heteroaryl azobenzene derivatives have revealed superior properties to
4-(1-Methylamino)ethylidene-1,5-disubstituted pyrrolidine-2,3-diones: synthesis, anti-inflammatory effect and in silico approaches
Beilstein J. Org. Chem. 2025, 21, 817–829, doi:10.3762/bjoc.21.65
- , we report the synthesis of 4-(1-methylamino)ethylidene-1,5-disubstituted pyrrolidine-2,3-diones via a reversible transimination reaction between Schiff’ base (C=N) linkage-containing pyrrolidine-2,3-dione derivatives and methylamine with yields of 80 to 92%. In addition to nuclear magnetic resonance
- derivatives; iNOS; pyrrolidine-2,3-dione derivatives; pyrrolidine-2,3-diones; pyrrolidine-2,3-diones targeting reversible transimination reaction; Introduction Nitric oxide (NO) is an important signaling molecule in numerous physiological processes such as neuronal tranmission, immue response, inflammatory
- pyrrolidine-2,3-dione derivatives could inhibit biomacromolecules (DNA, BSA, mPGES-1 or CDKs) and consequently, enable them to be candidates for Alzheimer's disease [11], anti-inflammatory [12][13][14][15][16][17], and antitumor drug discovery [12]. Furthermore, pyrrolidine-2,3-diones are also important
Synthesis and photoinduced switching properties of C7-heteroatom containing push–pull norbornadiene derivatives
Beilstein J. Org. Chem. 2025, 21, 807–816, doi:10.3762/bjoc.21.64
- ) derivatives. Push–pull substitution on the 2 and 3 position as well as introduction of oxygen or nitrogen at position 7 of the NBD scaffold have led to the development of a new family of photoswitches. We studied the potential conversion of norbornadiene to quadricyclane (QC) isomers. As main investigation
- variations in the switching properties. However, it is important to note that altering one property typically impacts other characteristics as well [21][22]. In this regard, both the substitution of the NBD periphery to produce push–pull derivatives and the variation of the central scaffold itself have been
- explored. For instance, incorporation of a C2H4 moiety into the bridge led to the formation of [2.2.2]-bicyclooctadiene derivatives with increased storage capacities but significantly reduced half-lifes compared to analogues NBD derivatives [23][24]. Additionally, introduction of one or more heteroatoms at
Regioselective formal hydrocyanation of allenes: synthesis of β,γ-unsaturated nitriles with α-all-carbon quaternary centers
Beilstein J. Org. Chem. 2025, 21, 800–806, doi:10.3762/bjoc.21.63
- , achieving complete conversion within 30 min and yielding the desired α-quaternary nitrile 3a in 95% yield. Moreover, no byproducts, such as regioisomeric nitriles or derivatives from over-addition of allylaluminum, were observed. After having established the optimized reaction conditions, the substrate
Recent advances in the electrochemical synthesis of organophosphorus compounds
Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61
- . Studies showed that a Mn catalyst is critical for synthesizing derivatives of phenanthridine-based diarylphosphine oxides. The reaction yield decreased in the absence of the ligand, and eliminating both the ligand and manganese salt suppressed the reaction. Moreover, a slight decrease in the reaction
- derivatives of glycine with diarylphosphine oxide (R2P(O)–H) for the synthesis of 1-aminoalkylphosphine oxides without the use of any transition metal catalyst or external oxidant. In this conversion, 1-aminoalkylphosphine oxides were formed in an undivided cell using a carbon electrode as the anode and
- phosphine oxide radical. The coupling product was obtained via the reaction of a phosphine oxide radical with thiazole compound. In another study on heteroaromatic compounds' electrochemical C–P coupling reactions, Gao et al. [55] reported an electrochemical reaction of indole derivatives with trialkyl
Copper-catalyzed domino cyclization of anilines and cyclobutanone oxime: a scalable and versatile route to spirotetrahydroquinoline derivatives
Beilstein J. Org. Chem. 2025, 21, 749–754, doi:10.3762/bjoc.21.58
- report the copper-catalyzed synthesis of tetrahydroquinoline derivatives via a domino reaction of aniline with cyclobutanone oxime. This method demonstrates a selective approach for generating bioactive tetrahydroquinoline scaffolds, which have broad applications in pharmaceutical chemistry. The reaction
- conditions were optimized for the effective formation of tetrahydroquinoline derivatives with varying substituents, showing high yields under mild conditions. Mechanistic studies suggest a catalytic cycle involving nucleophilic attack by the aniline on the cyclobutanone oxime, followed by cyclization to form
- pivotal structural elements in drug discovery [1][2][3][4]. Notably, tetrahydroquinoline derivatives featuring a strain-inducing ring system are prevalent in numerous bioactive molecules, including those with promising therapeutic potential for neurological disorders, oncology, and various other medical
Orthogonal photoswitching of heterobivalent azobenzene glycoclusters: the effect of glycoligand orientation in bacterial adhesion
Beilstein J. Org. Chem. 2025, 21, 736–748, doi:10.3762/bjoc.21.57
- ]. Specifically, the reversible E/Z isomerization of the azo group in azobenzene glycosides is suited to control the spatial presentation of glycoligands and, for example, switch carbohydrate-specific bacterial adhesion on and off [20][21][22][23]. Indeed, glycoazobenzene derivatives are excellent tools to
Synthesis of HBC fluorophores with an electrophilic handle for covalent attachment to Pepper RNA
Beilstein J. Org. Chem. 2025, 21, 727–735, doi:10.3762/bjoc.21.56
- , however, there was no complementary RNA-based tool with comparable live-cell-imaging properties. Based on the autocatalytically generated fluorophore 4-(p-hydroxybenzylidene)imidazolidin-5-one (HBI) in GFP, in vitro selection on derivatives of HBI led to the discovery of the first fluorogen-activating
- (8), MsOc3HBC (14), and MsOc3HBC-vinyl (22)) as reported previously [11]. Nine more HBC derivatives with altered handle lengths and different electrophilic groups are introduced in this study. Furthermore, we include an evaluation of the efficiency of all reactive fluorophores (previously introduced
- )cyanophenylacetonitrile, called HBC [7]. This typical push–pull fluorophore uses a dialkylamino group as the electron donor and a cyano group as the electron acceptor, while the connecting conjugating system has been varied to obtain a series of derivatives covering a broad spectral range (Scheme 1) [7][12]. All of these
Origami with small molecules: exploiting the C–F bond as a conformational tool
Beilstein J. Org. Chem. 2025, 21, 680–716, doi:10.3762/bjoc.21.54
- scaffolds – alkanes – then we will progress to ethers, alcohols, sugars, amines (and their derivatives), carbonyl compounds, peptides, and finally sulfur-containing compounds. By arranging the material in this way, we hope that newcomers to the field might be able to readily envisage ways to apply these
- 8) that adds to the hyperconjugation and intramolecular H-bonding phenomena [96]. The conformational effects of fluorination in these two derivatives (i.e., esters and protonated alcohols) have been little exploited to date in the design of functional molecules [111]. However, one standout example
- oxocarbenium intermediate [136]. Another way that fluorine can alter the shapes of furanoses, is by replacing the ring oxygen. For example, compare the nucleotide derivatives 69 and 70 (Figure 9). When the ring oxygen of 69 is replaced with a fluoromethylene group in 70, the latter molecule adopts an unusual
Photochemically assisted synthesis of phenacenes fluorinated at the terminal benzene rings and their electronic spectra
Beilstein J. Org. Chem. 2025, 21, 670–679, doi:10.3762/bjoc.21.53
- of phenacene cores could produce a functional aromatic material alternative to fluorinated acenes. In this context, it would be of interest to construct highly fluorinated phenacene derivatives and reveal their structural and electronic natures in order to develop future organic functional molecules
Asymmetric synthesis of fluorinated derivatives of aromatic and γ-branched amino acids via a chiral Ni(II) complex
Beilstein J. Org. Chem. 2025, 21, 659–669, doi:10.3762/bjoc.21.52
- acids [11][12]. Recently, our working group presented the synthesis of a broad range of fluorinated derivatives of different canonical and non-canonical amino acids (Scheme 1) [13]. Besides the linear fluorinated versions of α‑aminobutyric acid and norvaline, the β‑branched fluorinated amino acids such
- , we introduce our attempts to synthesize the trifluorinated derivatives of leucine: (2S,4S)-trifluoroleucine ((2S,4S)-TfLeu) and (2S,4R)-trifluoroleucine ((2S,4R)-TfLeu) (Scheme 1). Here, we were especially interested in exploring the applicability of the Ni-based strategy to the synthesis of γ
- quantitative yield and with a great enantiomeric excess of >99% ee (Scheme 2). Trifluorinated derivatives of leucine The fluorinated alkyl iodide is commercially available but costly. Thus, we aimed at establishing an appropriate synthesis for this iodide. Our previous work showed that fluorinated alkyl
Recent advances in allylation of chiral secondary alkylcopper species
Beilstein J. Org. Chem. 2025, 21, 639–658, doi:10.3762/bjoc.21.51
- styrenes with diverse electronic properties as well as those containing sensitive functional groups such as esters, amides, and vinyl halides, to yield the desired β-chiral olefins in high enantioselectivity. Notably, the methodology could even be applied to vinylferrocene and vinylsilane derivatives
Entry to 2-aminoprolines via electrochemical decarboxylative amidation of N‑acetylamino malonic acid monoesters
Beilstein J. Org. Chem. 2025, 21, 630–638, doi:10.3762/bjoc.21.50
- under constant current conditions in aqueous acetonitrile and provides access to N-sulfonyl, N-benzoyl, and N-Boc-protected 2-aminoproline derivatives. Keywords: anodic oxidation; decarboxylation; electrosynthesis; Hofer–Moest reaction; non-proteinogenic amino acids; Introduction Non-proteinogenic
- and the development of efficient synthetic methods to access these medicinally relevant structural motifs. Herein, we report an electrochemical synthesis of 2-aminoproline and 2-aminopipecolic acid derivatives 6 (Figure 1). Recently, we disclosed an electrochemical approach to tetrahydrofuran and
- tetrahydropyran-containing amino acid derivatives via anodic decarboxylation of N-acetylamino malonic acid monoesters to generate a stabilized carbocation (Hofer–Moest conditions), which were then reacted with a tethered oxygen nucleophile [4]. In this follow-up study, we demonstrate that N-protected amines are
Photocatalyzed elaboration of antibody-based bioconjugates
Beilstein J. Org. Chem. 2025, 21, 616–629, doi:10.3762/bjoc.21.49
- derivatives round out the most predominant reactions used on non-natural amino acids. However, even though bioengineering allows the incorporation of non-canonical amino acids with astounding effectiveness and near-complete selectivity, this technology is exceedingly expensive and time-consuming, and the
Semisynthetic derivatives of massarilactone D with cytotoxic and nematicidal activities
Beilstein J. Org. Chem. 2025, 21, 607–615, doi:10.3762/bjoc.21.48
- Massarilactones constitute a rare class of polyketides produced mainly by endophytic fungi. Given that semisynthetic derivatives often exhibit biological activities greater than those of the substrates, seven previously unreported derivatives of massarilactone D, compounds 2–8, were synthetized by acylation with
- , epidermoid carcinoma A431, ovarian carcinoma SKOV-3, and breast cancer MCF-7 cell lines. Compounds 2 and 3 exhibited significant cytotoxicity against all the tested cells. Some of the semisynthetic derivatives were also tested for their nematicidal activity and compound 4 displayed significant and selective
- products can serve as effective scaffold for the design and synthesis of derivatives with improved biological activities [5][6][7]. Massarilactones are produced by marine and endophytic fungi and bear close biogenetic similarity to several other fungal PKS1-derived metabolites including rosigenin, the
Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions
Beilstein J. Org. Chem. 2025, 21, 601–606, doi:10.3762/bjoc.21.47
- valuable for the synthesis of related natural products and their derivatives. Representative sesquineolignan compounds. Retrosynthetic analysis of (±)-simonsol C. The first total synthesis of (±)-simonsol C by Banwell’s group. The second total synthesis of (±)-simonsol C developed by the Qin group. Rapid
Sequential two-step, one-pot microwave-assisted Urech synthesis of 5-monosubstituted hydantoins from L-amino acids in water
Beilstein J. Org. Chem. 2025, 21, 596–600, doi:10.3762/bjoc.21.46
- antibacterial [1], antiviral [2], anticancer [3], anti-inflammatory [4], and anticonvulsant [5]. Hydantoins were traditionally accessed from amino acids by conversion to urea derivatives followed by cyclization (Urech reaction) or from carbonyl compounds through the cyanohydrin intermediate (Bucherer–Bergs) [6
- Discussion As the first step of Urech hydantoin synthesis involved the N-carbamylation of amino acids, we carried out the microwave-assisted synthesis of urea derivatives in water, utilizing ʟ-phenylaniline as the representative amino acid. The optimal conditions for the N-carbamylation of ʟ-phenylaniline
Formaldehyde surrogates in multicomponent reactions
Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45
- this context, quinoline and its derivatives are privileged structures in several natural products and biologically active compounds, rendering this scaffold an important synthetic target. An attractive strategy to afford tetrahydroquinolines and quinolines is the Povarov reaction, a type of aza-Diels
- derivatives are isolated as side-products. Interestingly, when Liu et al. [40] modified this reaction by using a copper(II) catalyst under aerobic oxidative conditions, the regioisomers III (2-arylquinolines) were obtained (Scheme 9). To rationalize this singular result, the authors proposed a mechanism in
- consequently, different catalytic strategies to afford the electrophilic addition on the final cyclization step. Finally, other examples show the synthesis of 3-aryl and alkyl quinoline-3-carboxylate derivatives under acid catalysis for the activation of DMSO via the Pummerer reaction (Scheme 10). In these
Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophiles
Beilstein J. Org. Chem. 2025, 21, 556–563, doi:10.3762/bjoc.21.44
- ][9]. Wherein, the wide variety of easily available starting butenolides and amines allows one to create a huge array of practically useful products. At the same time, the application of hydrazine derivatives expands the range of formed heterocycles. So, along with the aforementioned N-substituted
- process with hydrazine derivatives is known in the literature. Therefore, the study of recyclizations of heterocyclic systems containing the 3-acylfuran-2(5H)-one core under action of various hydrazines is of a great interest. Ongoing our research in the field of allomaltol chemistry in the present
- and allomaltol derivatives have the wide variety of biological activity [12][13][14][15][16]. This means that designing such hybrid products can significantly alter the pharmacological properties. Results and Discussion The starting compounds 1 were prepared from allomaltol employing a previously
Binding of tryptophan and tryptophan-containing peptides in water by a glucose naphtho crown ether
Beilstein J. Org. Chem. 2025, 21, 541–546, doi:10.3762/bjoc.21.42
- peptides for binding we prepared the derivatives of peptides 2–4 bearing an acetyl-capped N-terminus (compounds 5–7). As a control we also studied tripeptide 8 containing exclusively alanine residues. The binding of tripeptides was again studied by ITC and fluorescence spectroscopy and the results are
Vinylogous functionalization of 4-alkylidene-5-aminopyrazoles with methyl trifluoropyruvates
Beilstein J. Org. Chem. 2025, 21, 533–540, doi:10.3762/bjoc.21.41
- . Several homoallylic trifluoromethyl carbinols functionalized with a pyrazole moiety were obtained under mild reaction conditions (27–80% yield). This methodology provides a straightforward access to an unprecedented class of trifluoromethyl carbinol derivatives offering a new synthetic approach to
Cryptophycin unit B analogues
Beilstein J. Org. Chem. 2025, 21, 526–532, doi:10.3762/bjoc.21.40
- derivatives lack a covalent attachment handle. By making use of drug conjugates, toxic payloads such as cryptophycins can be selectively delivered to the target site. We present the synthesis of two conjugable cryptophycins with amino groups in unit B, representing potential payloads for drug conjugates
- -phenyl position of unit A [9][10][11] or derivatisation of unit A’s epoxide moiety into a halohydrin (-glycinate) [5][12][13][14][15][16][17]. Cryptophycins modified at the α-position of unit C [18] and, most recently, various derivatives with modifications in unit D [19] were established as potent and
- of, firstly, m-chloro-p-(methylamino) derivative 1 to dissect the structure–activity relationship between the primary (IC50(CCRF-CEM) = 0.58 nM), secondary, and tertiary amine (IC50(CCRF-CEM) = 54 pM) derivatives [20]. Secondly, p-(dimethylamino) derivative 2 was synthesised to investigate the effect
Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene
Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39
- photostability compared to ANTH and 9,10-ANTH derivatives, and a simple synthetic access makes it an attractive material as a deep-blue OLED emitter and an efficient fluorescent probe. Keywords: anthracene; dibromoanthracene; electron poor polyaromatic systems; fluorescence; perfluoroalkylation
- have promising applications in optoelectronics. For example, investigation of the photophysical and electronic properties of ANTH began in the 1960s [1][2][3], and since then many new ANTH derivatives have been synthesized and explored for their use as fluorescent probes, organic semiconductors, and
- , the size and conformational flexibility of the five BnF groups resulted in significant disruption of CORA–CORA π–π interactions due to the greater CORA–CORA bowl-to-bowl distances relative to the less bulky C5-CORA(CF3)5 analogue [18][19]. However, corannulene derivatives are only weakly fluorescent
Synthesis of the aggregation pheromone of Tribolium castaneum
Beilstein J. Org. Chem. 2025, 21, 510–514, doi:10.3762/bjoc.21.38
- , Mori and Phillips achieved the complete separation of the derivatives from the four stereoisomers by reversed-phase HPLC at −54 °C, and revealed that the natural pheromone consists of four stereoisomers of 4,8-dimethyldecanal (Figure 1) [16][17]. Previous syntheses mainly focused on chiral sources of
Other Beilstein-Institut Open Science Activities
