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Search for "O-" in Full Text gives 2167 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Unraveling cooperative interactions between complexed ions in dual-host strategy for cesium salt separation

  • Zhihua Liu,
  • Ya-Zhi Chen,
  • Ji Wang,
  • Qingling Nie,
  • Wei Zhao and
  • Biao Wu

Beilstein J. Org. Chem. 2025, 21, 845–853, doi:10.3762/bjoc.21.68

Graphical Abstract
  • carbonyl (C=O) groups, as well as direct ion-pairing interactions between 18-crown-6-complexed Cs+ and hexaurea-bound PO43−. Single-crystal structural analysis corroborates these interactions, shedding light on the underlying mechanisms and providing valuable guidance for the rational design of advanced
  • , only two examples provide clear evidence of cooperative interactions based on single crystal structures [28][29], where the 18-crown-6 complexed K+ cation forms ion-dipole interactions with the carbonyl (C=O) or nitro (NO2) groups of the anion-bound receptors (KF and K2CO3). Recently, we demonstrated
  • interactions between K+ and C=O moieties [31], similar to these seen in the single crystal structures of KF and K2CO3 complexes. These provide a promising opportunity that can be used to identify the cooperative interaction underpinning complexed ions in dual-host strategy-based extraction. To do this, the
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Published 29 Apr 2025

4-(1-Methylamino)ethylidene-1,5-disubstituted pyrrolidine-2,3-diones: synthesis, anti-inflammatory effect and in silico approaches

  • Nguyen Tran Nguyen,
  • Vo Viet Dai,
  • Luc Van Meervelt,
  • Do Thi Thao and
  • Nguyen Minh Thong

Beilstein J. Org. Chem. 2025, 21, 817–829, doi:10.3762/bjoc.21.65

Graphical Abstract
  • -hybridized carbon atom directly bonded to the nitrogen atom of the secondary amino group of compound 5a. In the structure of each pyrrolidine-2,3-dione derivative 3a–e, there is an α,β-unsaturated ketone moiety in which the π systems of the C=C and C=O bonds could overlap each other to yield an extended
  • a dihedral angle of 49.86(10) 86.22(11)° with the phenyl rings C6–C11 and C18–C23, respectively. The angle between both phenyl rings is 70.76(11)°. The stereochemistry around the double bond is Z, allowing an intramolecular N–H···O hydrogen bond between one of the carbonyl oxygen atoms and the amino
  • group (Table S2 in Supporting Information File 1). The N and C atoms of the 1-methylamino)ethylidene group are coplanar with the pyrrolidine ring (max. deviation of 0.074(2) Å for atom C17). The molecules form inversion dimers through N–H···O hydrogen bonding. Despite the presence of aromatic rings, no
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Published 24 Apr 2025

Synthesis and photoinduced switching properties of C7-heteroatom containing push–pull norbornadiene derivatives

  • Daniel Krappmann and
  • Andreas Hirsch

Beilstein J. Org. Chem. 2025, 21, 807–816, doi:10.3762/bjoc.21.64

Graphical Abstract
  • . Starting with 1-((bromoethynyl)sulfonyl)-4-methylbenzene, which was previously prepared and characterized [40][41], Diels–Alder reaction with either cyclopentadiene, furan or Boc-protected pyrrol, resulted in the NBD precursors C-NBD1, O-NBD1 and N-NBD1, respectively [31][42]. With these precursors in hand
  • the corresponding boronic acid in a degassed toluene/H2O mixture (4:1, v/v) which was heated to 80 °C for 18 h (for detailed information see Supporting Information File 1). Using the described procedure, the oxygen containing derivatives O-NBD2 and nitrogen substituted N-NBD2 were successfully
  • . Photoswitching The photoswitching of the NBDs to corresponding QCs was monitored by UV–vis and 1H NMR spectroscopy. With increasing electronegativity of the bridge-atom, a slight bathochromic shift in the absorption spectra of the parent NBD precursors O-NBD1 and N-NBD1 was found (Figure 2a and 2c). For the
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Published 22 Apr 2025

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

  • Seeun Lim,
  • Teresa Kim and
  • Yunmi Lee

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

Graphical Abstract
  • , ethyl, phenethyl, and allyl groups, also underwent smooth cyanation, resulting in α-quaternary nitriles 3f–i in yields of 85–94%. Furthermore, aryl-substituted allenes 1j–o, incorporating electron-donating or electron-withdrawing substituents such as methyl, fluoro, chloro, bromo, trifluoromethyl, or
  • methoxy groups on the phenyl ring, were compatible with the reaction, producing nitriles 3j–o in 88–93% yields. In particular, thienyl-substituted allene 1p was efficiently transformed into the desired nitrile 3p. We further demonstrated the versatility of this protocol using 1,1,3-trisubstituted allenes
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Published 17 Apr 2025

Recent advances in the electrochemical synthesis of organophosphorus compounds

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

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

Graphical Abstract
  • that when the reaction was carried out in the presence of TEMPO as a radical scavenger, a side product, TEMPO-P(O)R2, was formed (it was confirmed using high-resolution mass spectrometry). The results revealed that the reaction proceeded in a radical pathway (Scheme 1). Based on the cyclic voltammetry
  • 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
  • nickel as the cathode in the presence of tetrabutylammonium bromide (TBAB) at the constant current of 6 mA. The electrodes used in the reaction are all in plate form. The presence of TBAB causes the resulting bromide anion to oxidize to bromine radical and react with R2P(O)–H to produce a radical
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Published 16 Apr 2025

Development and mechanistic studies of calcium–BINOL phosphate-catalyzed hydrocyanation of hydrazones

  • Carola Tortora,
  • Christian A. Fischer,
  • Sascha Kohlbauer,
  • Alexandru Zamfir,
  • Gerd M. Ballmann,
  • Jürgen Pahl,
  • Sjoerd Harder and
  • Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2025, 21, 755–765, doi:10.3762/bjoc.21.59

Graphical Abstract
  • that silicon is bound via the carbonyl oxygen in 12, as also shown by DFT computations. This is further corroborated by observation of a 13C NMR signal at 146 ppm for an sp2 carbon in the backbone of the product, which fits better for a C=N than a C=O bond. Recovery of the catalyst resting state 7 is
  • -state structure, two bonds (Ca–O and Si–C) are broken, while a Si–O bond is simultaneously formed, in a concerted step implying a cyclic flow of six electrons in a five-membered ring. The isocyanide Ca–N–C bond angle in TS 11-12 lies between that of 7 and 9. While the replacement step is slow, and hence
  • (product O=C(C1=CC=C(Br)C=C1)NNC(C#N)CC2=CC=CC=C2, 2’’) contain the supplementary crystallographic data for this paper. These data are provided free of charge by The Cambridge Crystallographic Data Centre via http://www.ccdc.ac.uk/data request/cif. Supporting Information File 32: Synthetic procedures, 1H
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Published 14 Apr 2025

Copper-catalyzed domino cyclization of anilines and cyclobutanone oxime: a scalable and versatile route to spirotetrahydroquinoline derivatives

  • Qingqing Jiang,
  • Xinyi Lei,
  • Pan Gao and
  • Yu Yuan

Beilstein J. Org. Chem. 2025, 21, 749–754, doi:10.3762/bjoc.21.58

Graphical Abstract
  • to be compatible substrates, affording cyclo-O/S-containing STHQ derivatives 3ab and 3ac in good yields. Additionally, ester-functionalized cyclobutanones exhibited smooth reactivity with aniline, enabling the synthesis of substituted STHQ motifs 3ad and 3ae in satisfactory yields. Notably, when
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Published 09 Apr 2025

Orthogonal photoswitching of heterobivalent azobenzene glycoclusters: the effect of glycoligand orientation in bacterial adhesion

  • Leon M. Friedrich and
  • Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2025, 21, 736–748, doi:10.3762/bjoc.21.57

Graphical Abstract
  • conjugated to the 3- and the 6-position of a methyl mannoside scaffold (Figure 1, 1 (6βGlc3αMan)) [24]. Orthogonal photoswitching of the two glycoantennas is guaranteed by (i) ortho-fluorination of one azobenzene moiety and (ii) S-azobenzene versus O-azobenzene conjugation, resulting in significantly shifted
  • 3-O-(mannosyloxyazobenzene)-6-thio-mannoside 11 was employed, which was prepared according to a known procedure applied for the synthesis of the heterobivalent glycocluster 6βGlc3αMan 1 (cf. Supporting Information File 1, Scheme S1). The cross-coupling of thiol 11 with the azobenzene
  • α-ᴅ-mannopyranosyloxyazobenzene mannosides 6βGlc 3 and 6αMan 4 were prepared first (Scheme 2A). The synthesis of the β-ᴅ-glucopyranosyl mannoside 6βGlc 3 started from the literature-known S,O-acetylated mannoside 13 [35], which was chemoselectively deprotected at the 6-position employing DTT (1,4
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Published 08 Apr 2025

Acyclic cucurbit[n]uril bearing alkyl sulfate ionic groups

  • Christian Akakpo,
  • Peter Y. Zavalij and
  • Lyle Isaacs

Beilstein J. Org. Chem. 2025, 21, 717–726, doi:10.3762/bjoc.21.55

Graphical Abstract
  • , two aromatic o-xylylene walls, and four sulfonates as solubilizing ionic groups. In accord with these structural features, M1 binds a variety of hydrophobic and cationic guest molecules by the hydrophobic effect, π–π interactions, and electrostatic (ion–dipole and ion–ion) interactions. Although
  • ][66][67]. Previously, we have studied the influence of the length of the O(CH2)nSO3Na sidearm (n = 0, 2, 3, 4) and found that the M0 host – where the hydrophobic linker (CH2)n was completely removed – displayed higher binding affinity than M1 which we attributed to the location of the ionic group
  • closer to the ureidyl C=O portals [68][69]. However, a close examination of the structures of M0 and M1 show that the ionic group for M1 is a sulfonate and for M0 is a sulfate. Accordingly, M1 and M0 differ in two ways: a) different (CH2)n linker length and b) different ionic group (sulfonate versus
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Published 03 Apr 2025

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

  • Patrick Ryan,
  • Ramsha Iftikhar and
  • Luke Hunter

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

Graphical Abstract
  • fluorine atoms into the structure. The C–F bond has certain fundamental characteristics that enable it to serve as an effective conformational tool (Figure 1) [2][3][4]. First, the C–F bond is quite short at only ≈1.35 Å (cf. ≈1.09 Å for C–H, or ≈1.43 Å for C–O). The short length of the C–F bond, and the
  • happens if fluorine is introduced onto one of the carbons that is directly attached to oxygen (Figure 6). This makes possible a hyperconjugative interaction between a lone pair on oxygen and the σ* orbital of the C–F bond (I, Figure 6) [76]. This interaction biases the rotational profile about the O–C(F
  • pendant aryl moiety, is better for target-binding and hence 41 is a ≈10-fold more potent inhibitor of BACE-1 than 40. Several further examples of cyclic ethers will be examined in section 5 (sugars). The anomeric effect applies in acyclic ethers, too. Consider the non-fluorinated scaffold, Ph–O–CH3 (42
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Published 02 Apr 2025

Photochemically assisted synthesis of phenacenes fluorinated at the terminal benzene rings and their electronic spectra

  • Yuuki Ishii,
  • Minoru Yamaji,
  • Fumito Tani,
  • Kenta Goto,
  • Yoshihiro Kubozono and
  • Hideki Okamoto

Beilstein J. Org. Chem. 2025, 21, 670–679, doi:10.3762/bjoc.21.53

Graphical Abstract
  • napthalene-1,5-dicarboxaldehyde was protected as an acetal, was prepared through a 5-step reaction sequence. Phosphonium salt 5 [39] and the partly protected o-phthalaldehyde 6 [47] were obtained by previously reported procedures. The reaction of phosphonium salt 5 with aldehyde 6 in the presence of KOH and
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Published 24 Mar 2025

Recent advances in allylation of chiral secondary alkylcopper species

  • Minjae Kim,
  • Gwanggyun Kim,
  • Doyoon Kim,
  • Jun Hee Lee and
  • Seung Hwan Cho

Beilstein J. Org. Chem. 2025, 21, 639–658, doi:10.3762/bjoc.21.51

Graphical Abstract
  • significance of this transformation lies in its unique ability to efficiently create a stereogenic center while forming new carbon–carbon or carbon–heteroatom bonds (e.g., C–N, C–O, and C–S) with excellent selectivities. The field of metal-catalyzed allylic substitution has evolved significantly since its
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Published 20 Mar 2025

Entry to 2-aminoprolines via electrochemical decarboxylative amidation of N‑acetylamino malonic acid monoesters

  • Olesja Koleda,
  • Janis Sadauskis,
  • Darja Antonenko,
  • Edvards Janis Treijs,
  • Raivis Davis Steberis and
  • Edgars Suna

Beilstein J. Org. Chem. 2025, 21, 630–638, doi:10.3762/bjoc.21.50

Graphical Abstract
  • observed by LC–MS when the electrolysis was performed in 5:1 MeCN/D2O (Scheme 2, reaction 2). The considerably higher O–H bond dissociation energy (119 kcal/mol) [12] as compared to that of the C–H bond in MeCN (86 kcal/mol) [13] renders the hydrogen atom abstraction from water by a carbon-centered radical
  • undergo the decarboxylative cyclization, but also N-mesyl-protected monoester 9f could be converted into 2-aminoproline derivative 6f in 60% yield using a graphite cathode. However, the N-o-nosyl-protecting group is not compatible with the developed electrolysis conditions, likely because it undergoes an
  • of N-o-nosyl-protected monoester 9g was performed in a divided cell in the presence of NaOH as a base (1 equiv). Gratifyingly, by this route N-o-nosyl-protected 6g was obtained in 25% yield. The attempted synthesis of 2-aminopipecolic acid derivative 6h under the developed conditions was unsuccessful
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Published 19 Mar 2025

Semisynthetic derivatives of massarilactone D with cytotoxic and nematicidal activities

  • Rémy B. Teponno,
  • Sara R. Noumeur and
  • Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 607–615, doi:10.3762/bjoc.21.48

Graphical Abstract
  • -carbonyl group was linked through an ester bond and the only hydroxy group available for this esterification was the one at C-7. This compound was finally elucidated as massarilactone D 3,4-di-O-methacryloyl-7-O-(6-chloro-3,4-dihydro-2,5-dimethyl-2H-pyran-2-carbonyl). For the formation of compound 2, an
  • ]+ corresponding to the molecular formula C29H24O7. The presence of two cinnamoyl moieties was supported by resonances shown at δH 7.77 (d, J = 16.0 Hz, H-3'''), 7.76 (d, 16.0, H-3''), 7.72–7.70 (o, H-5'', H-9'', H-5''', H-9'''), 7.46–7.44 (o, H-6'', H-7'', H-8'', H-6''', H-7''', H-8'''), 6.60 (d, J = 16.0 Hz, H-2
  • ''), 129.3 (C-5''', C-9'''), 118.0 (C-2''), and 117.8 (C-2''') [19][20]. The HMBC correlations were observed from H-3 (δH 5.43, t, J = 3.6 Hz) to C-1''' (δC 165.7) and from H-4 (δH 5.90, o) to C-1'' (δC 165.9). The 1H NMR spectrum of compound 3 revealed the presence of two signals at δH 5.28 (d, J = 3.0 Hz
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Published 17 Mar 2025

Formaldehyde surrogates in multicomponent reactions

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

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

Graphical Abstract
  • , several efforts have been made to improve the chemoselectivity of the oxidation step. Among the most relevant examples, o-iodoxybenzoic acid (IBX) has been used in Ugi and Passerini reactions to oxidize the suitable alcohol to the desired aldehyde [13]. Alternatively, catalytic amounts of a ternary system
  • phosphites can also undergo an addition to the C=O bond of the carbonyl component (Abramov reaction) giving α-hydroxy phosphonates 33 as byproducts (Scheme 26a) [72]. Competition between the two nucleophiles for the electrophilic carbonyl compound depends on their relative reactivity [74][77] and this lack
  • of chemoselectivity becomes important when formaldehyde is used. Moreover, primary amines (alkyl- and arylamines) can also react with two equivalents of both the formaldehyde and the P(O)H compound. In this case, a double Kabachnik–Fields condensation gives bis(phosphorylmethyl)amines 34 as possible
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Published 13 Mar 2025

Synthesis of the aggregation pheromone of Tribolium castaneum

  • Biyu An,
  • Xueyang Wang,
  • Ao Jiao,
  • Qinghua Bian and
  • Jiangchun Zhong

Beilstein J. Org. Chem. 2025, 21, 510–514, doi:10.3762/bjoc.21.38

Graphical Abstract
  • (R)-citronellic acid [18], methyl (S)-3-hydroxy-2-methylpropanoate, (S)-2-methyl-1-butanol [19], (R)-2,3-O-isopropylideneglyceraldehyde [20], (R)- and (S)-citronellol [21], (R)-4-methyl-δ-valerolactone [22], porcine pancreatic lipase (PPL)-catalyzed acetylation of racemic citronellol [23], and Evan′s
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Published 06 Mar 2025

Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye

  • Metodej Dvoracek,
  • Brendan Twamley,
  • Mathias O. Senge and
  • Mikhail A. Filatov

Beilstein J. Org. Chem. 2025, 21, 500–509, doi:10.3762/bjoc.21.37

Graphical Abstract
  • Metodej Dvoracek Brendan Twamley Mathias O. Senge Mikhail A. Filatov School of Chemical and Biopharmaceutical Sciences, Technological University Dublin, City Campus, Grangegorman, D07 ADY7 Dublin, Ireland School of Chemistry, Trinity College Dublin, The University of Dublin, Dublin 2, Ireland
  • groups play a role by increasing the number of hydrogen bonds (C–H···O, 3.18(5)–3.62(6) Å) The intermolecular distances between the C–H groups and the chlorine atoms in Cl2B (A) are C13A–H13···Cl1A, 3.69(5), and C18A–H18C···Cl2A, 3.69(3) Å, indicating further molecular attraction [22]. A previously
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Published 05 Mar 2025

Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction

  • Thomas Brandt,
  • Pascal Lentes,
  • Jeremy Rudtke,
  • Michael Hösgen,
  • Christian Näther and
  • Rainer Herges

Beilstein J. Org. Chem. 2025, 21, 490–499, doi:10.3762/bjoc.21.36

Graphical Abstract
  • biochemical reactions usually take place in aqueous environments [13]. The substitution of one CH2 group in the CH2CH2 bridge by N–C(=O)–CH3 leads to an intrinsic water solubility of the N-acetyl diazocine 1 (Figure 1) [3]. Furthermore the photoconversion of 1 shows no significant drop in pure water in
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Published 04 Mar 2025

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

Graphical Abstract
  • were required to obtain the corresponding mesylate 3b. Similar to 11, compound 12 was isolated as its trifluoroacetate salt. Selective Boc protection of the aliphatic amine gave 13, which was selectively O-mesylated to give compound 14. Compound 14 was found to slowly undergo intramolecular cyclization
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Published 04 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

Graphical Abstract
  • investigated. When o-terphenyl (10.1) was milled (30 Hz, PTFE balls) and irradiated (λ = 270 nm) in the presence of silica gel (bulking agent), I2 (1 equiv) as an oxidant, and K2CO3 (1 equiv) as a base in the presence of toluene, the expected product 10.2 was obtained in 81% yield after isolation upon 181 h of
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Published 03 Mar 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
  • carbonyl oriented outward (designated by “0” or “O”) and amide carbonyl oriented inward (designated by “1” or “I”). There are 64 (26) permutations of carbonyl orientations in our cages, of which 13 are unique for cage 1 after grouping by symmetry (and ignoring enantiomers), which we have labelled as C1–C13
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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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  • Barcelona, Spain 10.3762/bjoc.21.29 Abstract A new series of o-carborane-fused pyrazoles has been recently successfully synthesized. This fusion was expected to create a hybrid 3D/2D aromatic system, combining the 3D aromaticity of o-carborane with the 2D aromaticity of pyrazole. However, while the boron
  • 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
  • ], offering enhanced properties and efficacy [28][30][33][34][35]. Therefore, the advancement of simple, efficient methodologies for synthesizing o-carborane-fused heterocycles is critically needed. However, the limited number of synthetic strategies for carborane functionalization [36] continues to constrain
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Published 21 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

Graphical Abstract
  • achieve better stereocontrol and to facilitate the formation of synthetically challenging glycosidic linkages. Keywords: chemical O-glycosylation; neighbouring group participation; remote group participation; solvent effect; stereocontrol; Introduction Cell surface glycans in living cells have
  • , however, are used synonymously owing to their same participating property and the same Zemplén deprotection strategy [87]. A recent study showed the use of modified Zemplén conditions to synthesise deacetylated methyl β-glycopyranosides directly from per-O-acetylated α-glycosyl halides using a
  • neighbouring group participation for the formation of the acetoxonium ion intermediate was more favourable in the locked systems like o-substituted benzoyl groups instead of aliphatic protections. Many protecting groups have been developed for the protection of the amine functionality of nucleosides like 2
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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
  • 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 Vladimir I. Minkin Federal
  • Comprehensive Cancer Center at University of Alabama at Birmingham, Department of Medicine, Section of Hematology/Oncology, Heersink School of Medicine, Birmingham, AL 35233, USA 10.3762/bjoc.21.26 Abstract The acid-catalyzed reaction of benzo[e(g)] derivatives of 2,3,3-trimethylindolenines with o-chloranil
  • -(1,1-Dimethyl-1H-benzo[e]indolin-2-yl)-5,6,7-trichloro-1,3-tropolone exhibited high in vitro cytotoxic activity against A431 skin cancer and H1299 lung cancer cell lines. Keywords: cytotoxic activity; fluorescence; o-chloranil; quantum chemical DFT calculations; 1,3-tropolones; X-ray diffraction
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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

Graphical Abstract
  • ) products and with alkylating agents 6i–n to give the N- and O-alkylated (dialkylated) products. The alkylation of compound 5 was controlled by the molar quantities of alkylating agents and base present. Thus, compound 5 was N-alkylated using equimolar quantities of the alkylating agents 6a–h to give the
  • respective derivatives 7a–h. On the other hand, compound 5 was N-alkylated as well as O-alkylated using 2.0 equivalents of alkylating agents 6i–n to yield the respective derivatives 7i–n. The formation of monoalkylated derivatives is based on the fact that the NH group of the pyrazole ring in 5 is more
  • susceptible to alkylation than the OH group. However, under more basic conditions and using the alkylating agent in excess can lead to a dialkylated product. It has already been established that N-alkylation takes place before O-alkylation because the nitrogen atom is a softer nucleophile as compared to the
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Published 12 Feb 2025
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