Search results

Search for "O-" in Full Text gives 2175 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

2-Heteroarylethylamines in medicinal chemistry: a review of 2-phenethylamine satellite chemical space

  • Carlos Nieto,
  • Alejandro Manchado,
  • Ángel García-González,
  • David Díez and
  • Narciso M. Garrido

Beilstein J. Org. Chem. 2024, 20, 1880–1893, doi:10.3762/bjoc.20.163

Graphical Abstract
  • -phenethylamine derivatives evaluating affinity and aromatic core diversity. Description of the 2-heteroarylethylamine scope of the present review featuring appropriate heteroaromatic systems (A = O, N, S). 2-Aminoethylpyridine derivatives with therapeutic activity. 2-Aminoethylfuran derivatives with therapeutic
PDF
Album
Review
Published 02 Aug 2024

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

  • Cristina Martini,
  • Muhammad Idham Darussalam Mardjan and
  • Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

Graphical Abstract
  • significantly more active than 9, owing to higher rigidity and the correct position of the ortho H atoms in close proximity to the σ-holes on the I atom. The authors demonstrated that hydrogen bonding between H in ortho position of 8 and both O atom of aldehyde and N atom of imine significantly increased the
  • generated, the intermediates 105 and isocyanides underwent formal [4 + 1] cycloaddition followed by tautomerization, affording benzothiazolpyrroles 106 (X = S) in moderate to good yields (52–82%). In addition, performing the three-component reaction using benzoxazole acetonitrile 104 (X = O) or 2-pyridyl
  • acetonitrile (not shown) led to the formation of benzoxazolpyrroles 106 (X = O) and indolizines (not shown), respectively. The GBB reaction is a powerful tool for the construction of imidazo[1,2,a]pyridines. Khan et al. [69] envisioned an isocyanide-free protocol based on arylglyoxals 107, 2-aminopyridines and
PDF
Album
Review
Published 01 Aug 2024

A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts

  • Ivana Weisheitelová,
  • Radek Cibulka,
  • Marek Sikorski and
  • Tetiana Pavlovska

Beilstein J. Org. Chem. 2024, 20, 1831–1838, doi:10.3762/bjoc.20.161

Graphical Abstract
  • -dimethyldichloromethyleniminium chloride and the Vilsmeier reagent, or condensations between o-aminobenzaldehydes and barbituric acid [20][21][23][24][25][26][27]. Neither of these methods allows for the introduction of an aryl substituent into C(5), which confers unique chemical and physical properties on 5-aryldeazaalloxazines
  • derivatives 2i–k, we changed the solvent to DMF/AlCl3, which increased the yields to 41–45%. However, the 7-methoxy derivative 2l with o-methyl substituent in the aldehyde moiety precipitated in DMSO after two days of reaction time. Interestingly, we observed only traces of another possible regioisomer 2m
  • the described conditions. The halogen groups on the anilines slightly decreased their reactivity, leading to the formation of products 2q–w with lower yields. However, the 8-chlorine derivative 2u with a o-tolyl aldehyde moiety was prepared with a yield of 37%. Aromatic aldehydes bearing bromine and
PDF
Album
Supp Info
Full Research Paper
Published 31 Jul 2024

Hetero-polycyclic aromatic systems: A data-driven investigation of structure–property relationships

  • Sabyasachi Chakraborty,
  • Eduardo Mayo Yanes and
  • Renana Gershoni-Poranne

Beilstein J. Org. Chem. 2024, 20, 1817–1830, doi:10.3762/bjoc.20.160

Graphical Abstract
  • number of heteroatoms of a certain type (section 2 of Supporting Information File 1). These plots (Figure S6 in Supporting Information File 1) made it readily apparent that the B atoms unsurprisingly accumulate in the regions of lower LUMO value and, to a lesser extent, higher HOMO values. The N, O, and
  • normalized according to the relative prevalence of the heteroatom in the dataset, which allows for a more straightforward comparison between different heteroatoms, as well as for the same heteroatom across the property range. Figure 7 shows that the likelihood of finding O and S atoms is relatively uniform
  • of O and S atoms, while the N likelihood remains rather uniform. The trends become even more pronounced in the plot of the Gap, as it is a sum of the HOMO and LUMO complementary effects. For the Gap and AIP, an increase in N towards higher values can be noted. For the AEA, the B clearly dominates the
PDF
Album
Supp Info
Full Research Paper
Published 31 Jul 2024

Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides

  • Samuel M. G. Dearman,
  • Xiang Li,
  • Yang Li,
  • Kuldip Singh and
  • Alison M. Stuart

Beilstein J. Org. Chem. 2024, 20, 1785–1793, doi:10.3762/bjoc.20.157

Graphical Abstract
  • ) are very similar to those in trifluoroiodane 20 (range from 1.956(4) to 1.984(4) Å), but are shorter than that in fluoroiodane 2 (2.048(3) to 2.058(3) Å) suggesting that fluorine is bound more strongly to the iodine(V) centre than in iodine(III) compounds. There is a similar contraction in the I–O
  • )°) deviates from 180°, but not to the same extent as seen with the aryl-IF4 compounds (169.9(1) to 170.4(1)°) or with trifluoroiodane 20 (167.9(2)° to 169.0(2)°) [24]. On the other hand, the O–I–O bond angle for difluoroiodane 6 (161.4(2)°) is much smaller than the F’–I–O bond angles in both trifluoroiodane
  • with the solid state structures. As expected, the calculated atomic charge on iodine was much higher for the iodine(V) fluorides (1.689–1.766) than in the iodine(III) fluorides (0.957–1.009) resulting in shorter I–F and I–O bond lengths. Interestingly, there is a slightly lower charge on iodine in
PDF
Album
Supp Info
Full Research Paper
Published 29 Jul 2024

Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations

  • Alexander V. Tsygankov,
  • Vladyslav O. Vereshchak,
  • Tetiana O. Savluk,
  • Serhiy M. Desenko,
  • Valeriia V. Ananieva,
  • Oleksandr V. Buravov,
  • Yana I. Sakhno,
  • Svitlana V. Shishkina and
  • Valentyn A. Chebanov

Beilstein J. Org. Chem. 2024, 20, 1773–1784, doi:10.3762/bjoc.20.156

Graphical Abstract
  • Alexander V. Tsygankov Vladyslav O. Vereshchak Tetiana O. Savluk Serhiy M. Desenko Valeriia V. Ananieva Oleksandr V. Buravov Yana I. Sakhno Svitlana V. Shishkina Valentyn A. Chebanov Institute of Functional Materials Chemistry, State Scientific Institution “Institute for Single Crystals” of
PDF
Album
Supp Info
Full Research Paper
Published 26 Jul 2024

Synthesis and characterization of 1,2,3,4-naphthalene and anthracene diimides

  • Adam D. Bass,
  • Daniela Castellanos,
  • Xavier A. Calicdan and
  • Dennis D. Cao

Beilstein J. Org. Chem. 2024, 20, 1767–1772, doi:10.3762/bjoc.20.155

Graphical Abstract
  • from the title compounds. Despite this different packing mode within the stack, the interstack interactions exhibited by 8-Ph are similar to those found in 7-Ph. Although there are still observable C–H···π interactions and C=O···H–C interactions between stacks, they appear to be weaker, as evidenced by
  • the longer interaction distances and interceding incorporation of CH2Cl2 (Figure 2b). Furthermore, in 8-Ph the interstack C=O···H–C interaction is skewed such as to involve only one C=O, compared to the symmetric dual-contact that is seen for 7-Ph. Optical and electronic characterization The
  • -Ph as determined by X-ray crystallography. Representative C=O···H–C and C–H···π interactions are indicated in teal and magenta, respectively. Top-down views of π-stacking modes in c) 7-Ph and d, e) 8-Ph. Hydrogen atoms have been removed for clarity in c–e. Atom color code: C = tan, H = white, Cl
PDF
Album
Supp Info
Full Research Paper
Published 25 Jul 2024

Harnessing unprotected deactivated amines and arylglyoxals in the Ugi reaction for the synthesis of fused complex nitrogen heterocycles

  • Javier Gómez-Ayuso,
  • Pablo Pertejo,
  • Tomás Hermosilla,
  • Israel Carreira-Barral,
  • Roberto Quesada and
  • María García-Valverde

Beilstein J. Org. Chem. 2024, 20, 1758–1766, doi:10.3762/bjoc.20.154

Graphical Abstract
  • different competitive reactions triggered by it, such as the interrupted Ugi reaction resulting from the competitive addition over the nitrilium intermediate [9][10] or the split-Ugi reaction arising from a competitive O,N-acyl transference on the imidate intermediate, through a remote Mumm rearrangement
  • [29], through post-condensation reactions. Following the methodology previously described in our group [30], the reduction of the nitro group on indole and pyrrole derivatives 9f,g,l–o (Scheme 9, Table 5) employing tin(II) chloride under acidic conditions in boiling n-butanol (120 °C) afforded the
PDF
Album
Supp Info
Full Research Paper
Published 25 Jul 2024

Synthesis of polycyclic aromatic quinones by continuous flow electrochemical oxidation: anodic methoxylation of polycyclic aromatic phenols (PAPs)

  • Hiwot M. Tiruye,
  • Solon Economopoulos and
  • Kåre B. Jørgensen

Beilstein J. Org. Chem. 2024, 20, 1746–1757, doi:10.3762/bjoc.20.153

Graphical Abstract
  • . The specific quinones formed were guided by the position of an initial hydroxy group on the polycyclic aromatic hydrocarbon. An available para-position in the PAPs gave p-quinones, while hydroxy groups in the 2- or 3-position led to o-quinones. The substrates were analysed by cyclic voltammetry for
  • properties make them privileged structures in medicinal chemistry [2]. Benzoquinone and naphthoquinone can exist as ortho-quinone and para-quinone, with the latter considered more stable [5]. Additionally, p- and o-quinones are formed in metabolism of drugs [6] as well as polycyclic aromatic hydrocarbons
  • radical (potassium nitrosodisulfonate) [13] or catalytic systems like methyltrioxorhenium(VII) (MeReO3) [14] and 2-iodobenzenesulfonic acids (IBS)/Oxone® [15] led to either p-quinones or o-quinones, depending on the substituents in the para-position to the hydroxy group. Recently, hypervalent iodine
PDF
Album
Supp Info
Full Research Paper
Published 24 Jul 2024

Syntheses and medicinal chemistry of spiro heterocyclic steroids

  • Laura L. Romero-Hernández,
  • Ana Isabel Ahuja-Casarín,
  • Penélope Merino-Montiel,
  • Sara Montiel-Smith,
  • José Luis Vega-Báez and
  • Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

Graphical Abstract
  • reaction of mestranol acetate (34) catalysed by a palladium(II) complex, in the presence of p-benzoquinone under carbon monoxide. The authors propose an initial addition of the acetate C=O group onto the triple bond coordinated to palladium, followed by a MeOH attack onto the resulting oxycarbenium, and a
PDF
Album
Review
Published 24 Jul 2024

Chemo-enzymatic total synthesis: current approaches toward the integration of chemical and enzymatic transformations

  • Ryo Tanifuji and
  • Hiroki Oguri

Beilstein J. Org. Chem. 2024, 20, 1693–1712, doi:10.3762/bjoc.20.151

Graphical Abstract
  • of scaffold 6 yield a series of intermediates and natural products, including cotylenol (1) and brassicicenes I and B (9 and 10), as well as brassicicene O (12), which possesses a distinct scaffold resulting from a skeletal rearrangement. To the core scaffold 6, the P450 enzymes, BscB and BscC
  • , introduce hydroxy groups at C8 and C16 to produce FD-8β,16-diol (7), and BscE-catalyzed O-methylation generates the putative intermediate 8. The subsequent oxidative allylic rearrangement (8→9), catalyzed by the nonheme iron(II) and 2-oxoglutarate (Fe(II)/2OG)-dependent dioxygenase BscD, was a key step
  • , and subsequent reduction of the exomethylene at C11–C18 catalyzed by BscH yield brassicicene O (12). Renata and co-workers successfully accomplished the chemoenzymatic total syntheses of cotylenol (1) and nine brassicicenes (Scheme 3) [19]. In the cyclization phase, a suitably functionalized 5/8/5
PDF
Album
Review
Published 23 Jul 2024

Methyltransferases from RiPP pathways: shaping the landscape of natural product chemistry

  • Maria-Paula Schröder,
  • Isabel P.-M. Pfeiffer and
  • Silja Mordhorst

Beilstein J. Org. Chem. 2024, 20, 1652–1670, doi:10.3762/bjoc.20.147

Graphical Abstract
  • bonds and primary amines of the amino acid chains are available for methylation, leading to poor site selectivity of any methylating reaction [39]. Therefore, either pre-methylated amino acids or short methylated peptides are incorporated into the full-length peptide. Direct O-methylation of an O
  • pathways Methyltransferases can be classified based on various factors, such as their substrates (small molecule MTs, protein MTs, or RNA/DNA MTs), the atom that accepts the methyl group (oxygen = O-MTs, nitrogen = N-MTs, carbon = C-MTs, sulphur = S-MTs, or halide = H-MTs), metal or cofactor dependence
  • atom, describing O-, N-, C-, and S-MTs; halide MTs have not (yet) been identified in RiPP pathways. The enzymes described below are either conventional SAM-dependent MTs or radical SAM (rSAM) MTs; rSAM MTs are one subfamily of the large rSAM enzyme superfamily, which encompasses enzymes catalysing a
PDF
Album
Review
Published 18 Jul 2024

Polymer degrading marine Microbulbifer bacteria: an un(der)utilized source of chemical and biocatalytic novelty

  • Weimao Zhong and
  • Vinayak Agarwal

Beilstein J. Org. Chem. 2024, 20, 1635–1651, doi:10.3762/bjoc.20.146

Graphical Abstract
  • from Microbulbifer Agarases Agarose is a natural polymer consisting of a linear chain of alternating residues of 3-O-linked β-ᴅ-galactopyranose and 4-O-linked 3,6-anhydro-α-ʟ-galactose. Agarose is a major component of agar, a polysaccharide present in the cell walls of some red algae [101]. Agarases
  • homo- and heteropolymeric forms. The 1,4-O-linkage in alginate is cleaved by alginate lyases, in a β-elimination manner (Figure 3). Alginate lyases can be either endolyases, or exolyases with preference for polyM or polyG present in the alginate matrix [110]. Alginate lyases have been isolated from
  • . coli from a marine Microbulbifer sp. ALW1 [59]. Enzyme structure and site-directed mutagenesis led to the identification of key residues in the enzyme active site that participated in the hydrolytic activity [59]. Carbohydrate esterases Carbohydrate esterases (CEs) catalyze the O- or N-deacylation of
PDF
Album
Review
Published 17 Jul 2024

New triazinephosphonate dopants for Nafion proton exchange membranes (PEM)

  • Fátima C. Teixeira,
  • António P. S. Teixeira and
  • C. M. Rangel

Beilstein J. Org. Chem. 2024, 20, 1623–1634, doi:10.3762/bjoc.20.145

Graphical Abstract
  • chlorine atoms by different nucleophiles. The devised strategy involved the attack of the O or N atoms of the arylphosphonate nucleophile at the position of the chlorine atom of triazine, at its 2, 4 and 6 carbon positions (Figure 1). Most of these nucleophiles bearing a phosphonate group were not
  • observed in the spectra of new membranes compared to commercial Nafion [64]. Other characteristic bands of S–O group, CF2–CF and C–O–C are observed at near 1050, 980 and 960 cm−1, respectively, in the FTIR spectra [63]. The proton conductivity of the new proton exchange membrane is a key property relevant
PDF
Album
Supp Info
Full Research Paper
Published 17 Jul 2024

pKalculator: A pKa predictor for C–H bonds

  • Rasmus M. Borup,
  • Nicolai Ree and
  • Jan H. Jensen

Beilstein J. Org. Chem. 2024, 20, 1614–1622, doi:10.3762/bjoc.20.144

Graphical Abstract
  • XGBoost. They trained on experimental pKa values in 39 solvents from the “internet Bond-energy Databank” (iBonD). Thus, they could predict the lowest pKa value for a wide range of molecules that contain bonds such as N–H, O–H, C–H, S–H, and P–H. However, they reported a scarcity of non-aqueous pKa values
PDF
Album
Supp Info
Full Research Paper
Published 16 Jul 2024

Generation of multimillion chemical space based on the parallel Groebke–Blackburn–Bienaymé reaction

  • Evgen V. Govor,
  • Vasyl Naumchyk,
  • Ihor Nestorak,
  • Dmytro S. Radchenko,
  • Dmytro Dudenko,
  • Yurii S. Moroz,
  • Olexiy D. Kachkovsky and
  • Oleksandr O. Grygorenko

Beilstein J. Org. Chem. 2024, 20, 1604–1613, doi:10.3762/bjoc.20.143

Graphical Abstract
  • Evgen V. Govor Vasyl Naumchyk Ihor Nestorak Dmytro S. Radchenko Dmytro Dudenko Yurii S. Moroz Olexiy D. Kachkovsky Oleksandr O. Grygorenko Enamine Ltd., Winston Churchill Street 78, Kyїv 02094, Ukraine Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyїv 01601, Ukraine V. P
  • } and 1{8}) or showed low conversion (halogenated derivatives 1{9–11}); 4-aminopyrimidines 1{12–16} also demonstrated low conversion; pyridine derivatives with electron-withdrawing substituents (such as NO2 at C-3 or C-5 positions, as well as CN, SO2NH2, or C(O)NH2 at the C-3 atom) did not work
  • aromatic aldehydes (e.g., 2{1–3}) did not work in the GBB reaction (Figure 4). This result is in accordance with the previous findings [21]. Notably, steric effects were not significant since o,o′-disubstituted aldehydes (e.g., 2{4–6}) displayed usual efficiency. As might be expected from our previous
PDF
Album
Supp Info
Full Research Paper
Published 16 Jul 2024

Supramolecular assemblies of amphiphilic donor–acceptor Stenhouse adducts as macroscopic soft scaffolds

  • Ka-Lung Hung,
  • Leong-Hung Cheung,
  • Yikun Ren,
  • Ming-Hin Chau,
  • Yan-Yi Lam,
  • Takashi Kajitani and
  • Franco King-Chi Leung

Beilstein J. Org. Chem. 2024, 20, 1590–1603, doi:10.3762/bjoc.20.142

Graphical Abstract
  • (Figure 1a). Upon 625 nm red-light irradiation for 60 s at 20 °C to reach the photostationary state (PSS), the strong absorption band at 470–685 nm was diminished, with a clear isosbestic point at 259 nm (Figure 1a, red line), which indicates a selective photoisomerization process from the open-isomer O
  • reversibility and photostability in organic solvent (Figure S1a and S1b, Supporting Information File 1). The photoisomerization between O-DA11 and C-DA11, upon irradiation with 625 nm red light and thermal back reaction in the dark, could be repeated for over five cycles, with only 5% absorbance decreases per
  •  1d and Figure 1f, blue line), the strong absorption band had recovered and indicated a selective photoisomerization process from the open-isomers O-DA7 and O-DA6 (Figure 1c–f, black and blue lines) to the cyclized-isomers C-DA7 and C-DA6 (Figure 1d and Figure 1f, red line). The results showed
PDF
Album
Supp Info
Full Research Paper
Published 15 Jul 2024

Divergent role of PIDA and PIFA in the AlX3 (X = Cl, Br) halogenation of 2-naphthol: a mechanistic study

  • Kevin A. Juárez-Ornelas,
  • Manuel Solís-Hernández,
  • Pedro Navarro-Santos,
  • J. Oscar C. Jiménez-Halla and
  • César R. Solorio-Alvarado

Beilstein J. Org. Chem. 2024, 20, 1580–1589, doi:10.3762/bjoc.20.141

Graphical Abstract
  • reactivity [9] usually associated with transition metals [10][11]. Iodine(III) compounds have been used for the formation of different bond types, such as C–C [12][13], C–O [14][15], C–N [16], C–S [17], C–CN [18], C–F [19][20][21], C–I [22][23], C–NO2 [24][25] and, in the context of this work, C–X (X = Cl
  • , the 6-31G(d) basis set was used for the other atoms (i.e., H, C, O, F, Al, etc.). Geometry optimizations were carried out without any symmetry constraints, and the stationary points were characterized by analytical frequency calculations, i.e., energy minima (reactants, intermediates, and products
  • 0 kcal/mol for more clarity. Herein, one chlorine atom is transferred from aluminum to the hypervalent iodine(III) center through six-membered-ring transition state TS1–Cl (ΔG‡ = 9.7 kcal/mol, selected bond lengths 2.76, 1.22, 1.27, 1.78, 2.60, and 2.86 Å for I–O, O–C, C–O, O–Al, Al–Cl, and Cl–I
PDF
Album
Supp Info
Full Research Paper
Published 15 Jul 2024

Mining raw plant transcriptomic data for new cyclopeptide alkaloids

  • Draco Kriger,
  • Michael A. Pasquale,
  • Brigitte G. Ampolini and
  • Jonathan R. Chekan

Beilstein J. Org. Chem. 2024, 20, 1548–1559, doi:10.3762/bjoc.20.138

Graphical Abstract
  • alkaloids, containing both Ziziphus and Ceanothus genera. In addition to the subclass defining Tyr-phenol-O to carbon linkage, the cyclopeptide alkaloids of this family are typically oxidatively decarboxylated and N-methylated (Figure 1, adouetine X and Figure 3, ceanothine B) [19][20][21]. Our
PDF
Album
Supp Info
Full Research Paper
Published 11 Jul 2024

Benzylic C(sp3)–H fluorination

  • Alexander P. Atkins,
  • Alice C. Dean and
  • Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 1527–1547, doi:10.3762/bjoc.20.137

Graphical Abstract
  • predominately considered to be stable to isolation conditions, secondary and tertiary suffer from the elimination of HF, especially in the presence of silica gel or glass vessels. Therefore, benzyl fluorides have been derivatised, for example in C–O, C–N and C–C bond-forming reactions [18][19][20], thereby also
  • was effective for the stereoselective fluorination of benzylic positions ortho to aldehyde substituents (Figure 9). The choice of a bulky amino, transient, directing group dictated the stereochemical outcome and promoted the C–F reductive elimination through an inner-sphere pathway. A competitive C–O
  • bond formation to afford the acyloxylation product was observed, and favoured when using directing groups with less steric bulk. This product had the opposite stereochemistry to the fluorination product suggesting it occurred via a competitive SN2 pathway. This is supported by the selectivity for C–O
PDF
Album
Review
Published 10 Jul 2024

Towards an asymmetric β-selective addition of azlactones to allenoates

  • Behzad Nasiri,
  • Ghaffar Pasdar,
  • Paul Zebrowski,
  • Katharina Röser,
  • David Naderer and
  • Mario Waser

Beilstein J. Org. Chem. 2024, 20, 1504–1509, doi:10.3762/bjoc.20.134

Graphical Abstract
  • azlactones 1 performed similarly as compared to the parent system 1a (products 5e–i), and analogous α-alkyl-substituted derivatives were reasonably well accepted too (5j–o). When varying the aryl substituent in position 2 of the oxazolone core (compare products 5a, 5g, and 5p) we found that increasing the
PDF
Album
Supp Info
Full Research Paper
Published 04 Jul 2024

Electrophotochemical metal-catalyzed synthesis of alkylnitriles from simple aliphatic carboxylic acids

  • Yukang Wang,
  • Yan Yao and
  • Niankai Fu

Beilstein J. Org. Chem. 2024, 20, 1497–1503, doi:10.3762/bjoc.20.133

Graphical Abstract
  • transformation (Figure 3B). Collectively, our experimental observations are in agreement with the proposed mechanistic picture detailed in Figure 3C. The anodically generated Ce(IV) carboxylates are able to undergo homolytic cleavage of the Ce–O bond upon light irradiation. The resulting carboxyl radical would
PDF
Album
Supp Info
Full Research Paper
Published 03 Jul 2024

Photoswitchable glycoligands targeting Pseudomonas aeruginosa LecA

  • Yu Fan,
  • Ahmed El Rhaz,
  • Stéphane Maisonneuve,
  • Emilie Gillon,
  • Maha Fatthalla,
  • Franck Le Bideau,
  • Guillaume Laurent,
  • Samir Messaoudi,
  • Anne Imberty and
  • Juan Xie

Beilstein J. Org. Chem. 2024, 20, 1486–1496, doi:10.3762/bjoc.20.132

Graphical Abstract
  • photoswitchable tools, few photochromic lectin ligands have been developed. We have designed and synthesized several O- and S-galactosyl azobenzenes as photoswitchable ligands of LecA and evaluated their binding affinity with isothermal titration calorimetry. We show that the synthesized monovalent glycoligands
  • experiences in photoswitchable glycosides and bacterial lectins [4][6][7][8][26][27][28][29][30][31], we have designed, synthesized, and characterized the first generation of O- and S-galactosyl azobenzenes as photoswitchable monovalent ligands targeting PA LecA. Their binding affinity with LecA evaluated by
  • -binding pocket, with the β-linked aromatic aglycons having five-fold higher affinity compared to aliphatic analogues [33][34]. Beside β-O-aryl galactosides, enzymatically more stable β-S-aryl galactosides have also been successfully developed as monovalent LecA ligands (Figure 1A) [30][35]. Since
PDF
Album
Supp Info
Full Research Paper
Published 03 Jul 2024

Synthesis of 2-benzyl N-substituted anilines via imine condensation–isoaromatization of (E)-2-arylidene-3-cyclohexenones and primary amines

  • Lu Li,
  • Na Li,
  • Xiao-Tian Mo,
  • Ming-Wei Yuan,
  • Lin Jiang and
  • Ming-Long Yuan

Beilstein J. Org. Chem. 2024, 20, 1468–1475, doi:10.3762/bjoc.20.130

Graphical Abstract
  • derivatives thereof. Synthesis of (E)-2-arylidene-3-cyclohexenones 2. Substrate scope of (E)-2-arylidene-3-cyclohexenones 2. Conditions: reactions were conducted with 2a–o (0.2 mmol) and 3a (2.0 mmol) were stirred in DME (2 mL) at 60 °C; Isolated yields; a2-Benzylaniline 4fa and 2-benzylphenol 5f were
PDF
Album
Supp Info
Full Research Paper
Published 02 Jul 2024

Rapid construction of tricyclic tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine via isocyanide-based multicomponent reaction

  • Xiu-Yu Chen,
  • Ying Han,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2024, 20, 1436–1443, doi:10.3762/bjoc.20.126

Graphical Abstract
  • can be performed with a wide variety of substrates. The molecular structure of the compound 6g was determined by single crystal X-ray diffraction method (Figure 2). The o-methoxyphenyl group exists on the trans-position of the fused pyrrolidine unit. The methoxycarbonyl group also exists on the cis
  • -position of the o-methoxyphenyl group. Therefore, compound 6g has the same relative configuration to that of the above mentioned product 3a, which also indicated that this reaction has same steric controlling effect. A plausible reaction mechanism is proposed in Scheme 1 to explain the formation of the
PDF
Album
Supp Info
Full Research Paper
Published 28 Jun 2024
Other Beilstein-Institut Open Science Activities