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Search for "DMSO" in Full Text gives 1029 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Synthetic approach to borrelidin fragments: focus on key intermediates

  • Yudhi Dwi Kurniawan,
  • Zetryana Puteri Tachrim,
  • Teni Ernawati,
  • Faris Hermawan,
  • Ima Nurasiyah and
  • Muhammad Alfin Sulmantara

Beilstein J. Org. Chem. 2025, 21, 1135–1160, doi:10.3762/bjoc.21.91

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  • alcohol was then protected as a PMB ether. After deprotecting the THP group, the resulting secondary alcohol was converted to a tosyl ester, which underwent an SN2 reaction with sodium cyanide in DMSO, yielding compound 109 with stereochemical inversion. Interestingly, reduction of the cyanide group with
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Published 12 Jun 2025

Investigations of amination reactions on an antimalarial 1,2,4-triazolo[4,3-a]pyrazine scaffold

  • Henry S. T. Smith,
  • Ben Giuliani,
  • Kanchana Wijesekera,
  • Kah Yean Lum,
  • Sandra Duffy,
  • Aaron Lock,
  • Jonathan M. White,
  • Vicky M. Avery and
  • Rohan A. Davis

Beilstein J. Org. Chem. 2025, 21, 1126–1134, doi:10.3762/bjoc.21.90

Graphical Abstract
  • °C in 5% CO2. At 6 h, 5 µL of 600 µM resazurin, diluted in growth media, was added. Plates were further incubated for 6 h and measured for fluorescence at 530 nm excitation and 595 nm emission. The % inhibition was calculated using 0.4% DMSO (no inhibition) and 50 μM puromycin (100% inhibition) data
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Published 10 Jun 2025

Recent advances in synthetic approaches for bioactive cinnamic acid derivatives

  • Betty A. Kustiana,
  • Galuh Widiyarti and
  • Teni Ernawati

Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85

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  • trimethylsulfoxonium iodide (TMSOI) with DMSO-d6, resulting in CH3/CD3 exchange. Furthermore, Chisholm and co-workers (2019) synthesized bulky cinnamate esters 61–64 utilizing a trichloroacetimidate-based alkylating agent in moderate to excellent yields via carbocation 65 formation upon trichloroacetamide release
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Published 28 May 2025

Synthesis of pyrrolo[3,2-d]pyrimidine-2,4(3H)-diones by domino C–N coupling/hydroamination reactions

  • Ruben Manuel Figueira de Abreu,
  • Robin Tiedemann,
  • Peter Ehlers and
  • Peter Langer

Beilstein J. Org. Chem. 2025, 21, 1010–1017, doi:10.3762/bjoc.21.82

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  • , 4l, and 4m in dichloromethane (c = 1·10−5 M). Synthesis of 3a–h. Conditions: i) Br2 (1.0 equiv), Ac2O (1.5 equiv), AcOH, 25 °C, 1 h [25]; ii) aryl acetylene (1.2 equiv), Pd(PPh3)Cl2 (5 mol %), CuI (5 mol %), NEt3 (10 equiv), DMSO, 25 °C, 6 h [26]. Yields of isolated products. C–N cross-coupling
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Published 22 May 2025

Harnessing tethered nitreniums for diastereoselective amino-sulfonoxylation of alkenes

  • Shyam Sathyamoorthi,
  • Appasaheb K. Nirpal,
  • Dnyaneshwar A. Gorve and
  • Steven P. Kelley

Beilstein J. Org. Chem. 2025, 21, 947–954, doi:10.3762/bjoc.21.78

Graphical Abstract
  • (Scheme 3A). The mesylate could be cleanly substituted with azide by heating substrate with excess NaN3 in DMSO (Scheme 3B). With an excess of Schwartz’s reagent, the carbonyl was cleanly reduced to give 1,3-oxazine 62. Contrary to what we had initially predicted from literature precedent, there was no
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Published 19 May 2025

Recent advances in controllable/divergent synthesis

  • Jilei Cao,
  • Leiyang Bai and
  • Xuefeng Jiang

Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73

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  • generated the [1 + 1] macrocycle 39 as the sole product. In contrast, polar aprotic solvents such as dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), or acetonitrile (MeCN) favored precipitation of the [2 + 2] macrocycle 40. Notably, the macrocycle 40 underwent spontaneous structural reorganization
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Published 07 May 2025

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
  • ]. According to our previous results, the binding affinity of L with chloride, sulfate and phosphate is determined to be 2.2 × 102 M−1, 9.9 × 104 M−1, and 3.8 × 106 M−1, respectively (in DMSO) [31]. Such strong anion binding affinity has led to selective extraction of sulfate and phosphate from basic aqueous
  • solution into chloroform and controllable release into acidic solution [32]. Very recently, it was found that the receptor L alone can further extract solid Li2SO4 into DMSO solution [33], where sulfate binding is sufficiently strong to drive the solid–liquid extraction. DFT calculations suggest that an
  • binding Na+ and K+ by oligourea foldamers and macrocycles [37][38][39]. However, in the solid−liquid extraction of Li2SO4 in DMSO, addition of crown ether did not help to increase the extraction efficiency. This is because ion-dipole interactions are negligible in high polar solvent, and Li+ binding is
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Published 29 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
  • α-ᴅ-mannoside (MeMan) measured on the same plate as reference. This leads to relative inhibitory potencies, so-called RIP values. Because of limited water solubility, the samples had to be dissolved in DMSO and therefore, the effect of pure DMSO was also tested in every individual assay (cf
  • . Supporting Information File 1, Figures S13–S16). DMSO is known for its bactericidal effect and still, the use of this organic solvent in bioassays is common [42]. In general, a DMSO concentration of less than 10% (v/v) is accepted as nontoxic [43]. In any case, the effect of DMSO in the assays was carefully
  • the conditions applied for the assay. This inhibitory effect is due to DMSO, which had to be used to dissolve the sample. Consequently, the RIP relative to DMSO is approx. 1 for both isomers of 3 (cf. Supporting Information File 1, Table S6). In all other cases, comparison of the RIP(MeMan) and the
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Published 08 Apr 2025

Synthesis of HBC fluorophores with an electrophilic handle for covalent attachment to Pepper RNA

  • Raphael Bereiter and
  • Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 727–735, doi:10.3762/bjoc.21.56

Graphical Abstract
  • observed for the HBC ether 11 (C4 homolog) and the bromoethoxyethyl HBC 9 (“C5” homolog). No reaction was observed for the C2 homolog 7 (Figure 2). Notably, the reaction yields for all derivatives increased when the DMSO content of the reaction mixture was increased from 5 to 15%. (DMSO was initially used
  • better solubility in the reaction buffer and did not require DMSO as co-solvent, making it a very promising candidate for in vivo applications. To complete the study, and given that the mesyloxy group has shown superior efficacy over all other functional groups tested for Pepper alkylation, we
  • additionally synthesized the HBC series with different linker lengths with the mesyloxy group, yielding the derivatives 16 to 18 (Scheme 5). All of these derivatives – although well soluble in the reaction buffer without the need for additional DMSO – were less reactive than N-(3-mesyloxypropyl) HBC derivative
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Published 04 Apr 2025

Sequential two-step, one-pot microwave-assisted Urech synthesis of 5-monosubstituted hydantoins from L-amino acids in water

  • Wei-Jin Chang,
  • Sook Yee Liew,
  • Thomas Kurz and
  • Siow-Ping Tan

Beilstein J. Org. Chem. 2025, 21, 596–600, doi:10.3762/bjoc.21.46

Graphical Abstract
  • min. The precipitates in the reaction mixture were filtered, washed with 1 M HCl solution (2 × 7 mL), distilled water (2 × 10 mL), and dried to afford H2a as a white solid. Yield 89%. [α]D20 −100.9 (c 11, CH3CN); 1H NMR (400 MHz, DMSO-d6) δ 10.44 (s, 1H), 7.93 (s, 1H), 7.17–7.30 (m, J = 8 Hz, 5H
  • ), 4.33 (td, J = 5, 1 Hz, 1H), 2.92 (m, J = 5 Hz, 2H); 13C NMR (100 MHz, DMSO-d6) δ 175.2, 157.2, 135.6, 129.8, 128.1, 126.7, 58.4, 36.4; LC–MS (ESI) m/z: 191 [M + H]+, 163, 120; HRMS (ESI) m/z: [M + H]+ calcd for C10H11N2O2 191.0815; found, 191.0815. The procedure was repeated by substituting ʟ
  • mixture was neutralized to pH 7 using saturated sodium bicarbonate solution and extracted with ethyl acetate multiple times. The organic extracts were combined, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to afford H2d as a white solid. Yield 70%. 1H NMR (400 MHz, DMSO-d6
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Published 14 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
  • , eventually, in other MCRs where formaldehyde acts as a C1 building block [16]. As can be seen in Scheme 3, under this strategy a wide variety of diamide compounds 1 could be afforded with very good yields applying MeOH as a formaldehyde source in a traditional Ugi reaction. Dimethyl sulfoxide (DMSO) as
  • surrogate and source of formaldehyde Dimethyl sulfoxide is a well-known polar-aprotic solvent with high boiling point that is used in several organic synthetic reactions because of affordable cost and relatively low toxicity. There are numerous examples that show the use of DMSO as a C1 or C2 building block
  • [17][18]. An important drawback of this solvent is the difficulty of its removal from the reaction crude, and extractions with water are commonly employed before purification. Depending on the reaction conditions, DMSO can be transformed into different products, e.g., under redox conditions, DMSO can
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Published 13 Mar 2025

Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene

  • Long K. San,
  • Sebastian Balser,
  • Brian J. Reeves,
  • Tyler T. Clikeman,
  • Yu-Sheng Chen,
  • Steven H. Strauss and
  • Olga V. Boltalina

Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39

Graphical Abstract
  • reaction in the presence of Cu in DMSO [22]. The former approach yielded a complex, inseparable mixture of products and was not studied further. The latter approach afforded two isolable main products, 9-ANTH(BnF) (14% yield) and 9,10-ANTH(BnF)2 (7% yield, both are isolated yields based on ANTH). Several
  • other, yet to be identified, ANTH(BnF)n compounds were also observed. In this reaction, ANTH dissolved in DMSO was heated to between 120 °C and 160 °C in the presence of 2 equiv of BnFI and 3 equiv of Cu powder as promotor for 24 h, resulting in the complete conversion of ANTH to reaction products. When
  • )n starting material. A series of reactions with 9,10-ANTH(Br)2 and BnFI in the presence of Cu were carried out in four high-boiling organic solvents: DMSO, chlorobenzene (PhCl), benzonitrile (PhCN), and N-methylpyrrolidinone (NMP). When PhCl was the solvent, the 14% yield of the mono-substituted
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Published 07 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
  • , geminal acid (S)-7 was decarboxylated with DMSO to yield chiral acid (S)-8 [33], followed by TiCl4-catalyzed reduction with ammonia-borane to obtain the chiral alkenyl alcohol (S)-9 [34]. The final tosylation with p-tosyl chloride provided (S)-3-methylhept-6-en-1-yl 4-methylbenzenesulfonate ((S)-10) [29
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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
  • shielding from light, and unavoidable light exposure during crystal selection, and the X-ray measurement itself. As an additional test, the compounds were prepared as NMR samples in DMSO-d6 and irradiated with 405 nm LED. Irradiation in the solution phase did not result in any dimerization; the respective
  • solid spread across the flask. The entire flask was then irradiated using 405 nm LEDs in the turntable chamber. Solution-phase irradiation tests For solution-phase irradiations, 10 mg of each compound was dissolved in DMSO-d6 and placed into NMR tubes. The samples were irradiated directly inside the
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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
  • neurotransmitters [10][11] or as switching units for potential dependent potassium channels [12]. Compared to the Z → E conversion rate of 92% (in n-hexane) of the parent diazocine the conversion in water/DMSO mixtures is decreasing with increasing water concentration (73% in water/DMSO 9:1) [8][9][10][11][12
  • ]. Moreover, the parent diazocine is insoluble in water (precipitation in water/DMSO > 9:1). Substitution with polar substituents such as CH2NH2 provides water solubility, however, it does not restore the high Z → E conversion rates of the parent system in organic solvents, which is a disadvantage, since
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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
  • , 70:30 anti/syn). This indicates a unique divergent photomechanochemical reaction pathway with respect to the simple irradiation in solid state. Remarkably, no selectivity was observed in solution state (DMSO as solvent), while a completely reversed selectivity (99%, anti/syn 91:9) was obtained when
  • -assisted grinding (LAG). This minimizes waste production compared to conventional solution-based methods. This is particularly advantageous when high-boiling point (e.g., DMSO) or noxious solvents (e.g., DMF and halogenated ones) are required. It is worth noting, however, that in some cases the heat
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Published 03 Mar 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
  • (Scheme 2). The structures of tautomeric forms of 7a, 7b, 8a, 8b and their energy characteristics were calculated by PBE0/6-311+G(d,p) method in the gas phase and polar solvent (DMSO) (Table 1, Figure 1 and Supporting Information File 3). According to the obtained data, the (NH) isomers of 7 and 8 are
  • characteristic values of chemical shifts and cross-peak analysis in two-dimensional spectra of 1H,1H COSY correlations, as well as 1H,13C correlations HSQC, HMBC, and 1H,15N HMBC spectra in DMSO-d6 and CDCl3 (Supporting Information File 2). In the 1H NMR spectrum of 7a in DMSO-d6, the signal of the weak field
  • proton is shifted to a stronger field of 14.23 ppm and appears as a narrow singlet (Supporting Information File 2, Figure S17). Analysis of two-dimensional correlation spectra of heteronuclear NMR spectroscopy shows that compound 7a in DMSO-d6 solution exists in the (NH) tautomeric form. Thus, in the 1H
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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

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  • prepared in DMSO and cancer cells were treated with 10 μM doses of compounds using the apoptosis inducing standard mensacarcin (10 μM) as a positive control [56]. Only compound 7l decreased cell viability to 63%, while the rest of the compounds showed very low to no significant decrease in cell viability
  • ethanol. Characterization data Solutions of all synthesized compounds 7a–h were prepared in DMSO-d6 and scanned for their 1H NMR spectra at 300 MHz and 13C NMR spectra at 75 MHz. The characterization data for compounds 7a–h is given in Supporting Information File 1. Antimicrobial assays The antimicrobial
  • experiments. Cytotoxic assays Single-dose MTT assays were performed for compounds 7a–n with the human colon cancer mammalian cell line (HCT-116, ATCC CCL-247) for evaluating the compounds’ inhibitory effects on cell viability [53][54][55][56]. Stock solutions of compounds were prepared in DMSO and cancer
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Published 12 Feb 2025

Synthesis of new condensed naphthoquinone, pyran and pyrimidine furancarboxylates

  • Kirill A. Gomonov,
  • Vasilii V. Pelipko,
  • Igor A. Litvinov,
  • Ilya A. Pilipenko,
  • Anna M. Stepanova,
  • Nikolai A. Lapatin,
  • Ruslan I. Baichurin and
  • Sergei V. Makarenko

Beilstein J. Org. Chem. 2025, 21, 340–347, doi:10.3762/bjoc.21.24

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  • data, they luminesce in DMSO solution when irradiated with light at wavelengths of 352 and 283 nm. Compounds 7a–f are capable of existing as lactim–lactam tautomers due to the presence of an amide fragment in their structure (Scheme 7). At the same time, the 1H and 13C NMR spectra of compounds 7a–f
  • indicate their individuality. The presence of a broadened signal in the 1H NMR spectra (DMSO-d6) in the region of 12.49–12.84 ppm and a C4 signal in the 13C NMR spectra (DMSO-d6) in the region of 158.1–159.0 ppm does not allow us to unambiguously determine the tautomeric form of compounds 7a–f in solution
  • Shimadzu UV-2401 PC spectrometer for samples in DMSO solutions in fused quartz cuvettes (optical path length 1.01 mm). Luminescence excitation spectra and luminescence spectra were recorded on a Shimadzu SF-6000 spectrofluorimeter in a 1 cm thick quartz cuvette at room temperature in a DMSO solution (c
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Published 12 Feb 2025

Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus Samsoniella aurantia

  • Rita Toshe,
  • Syeda J. Khalid,
  • Blondelle Matio Kemkuignou,
  • Esteban Charria-Girón,
  • Paul Eckhardt,
  • Birthe Sandargo,
  • Kunlapat Nuchthien,
  • J. Jennifer Luangsa-ard,
  • Till Opatz,
  • Hedda Schrey,
  • Sherif S. Ebada and
  • Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 327–339, doi:10.3762/bjoc.21.23

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  • ), 300 (0.5), 265 (0.6) 218 (2.4); NMR data (1H: 500 MHz, 13C: 125 MHz, DMSO-d6) see Table 1; HRESIMS m/z: [M – H2O + H]+ calcd for C25H28NO4+, 406.2026; found, 406.2020; [M + H]+ calcd for C25H30NO5+, 424.2118; found, 424.2126; [M + Na]+ calcd for C25H29NNaO5+, 446.1962; found, 446.1947. Farinosone A (2
  • . Beauvericin A (4): Yellow solid powder; UV–vis (MeOH) λmax: 344, 221 nm; NMR data (1H: 500 MHz in DMSO-d6) comparable to the previously described spectral data [14][15]; HRESIMS m/z: [M + H]+ calcd for C46H60N3O9+, 798.4324; found, 798.4324; [M + NH4]+ calcd for C46H63N4O9+, 815.4590; found, 815.4588; [M + Na
  • ]+ calcd for C46H59N3NaO9+, 820.4144; found, 820.4142. Beauvericin B (5): Yellow amorphous solid; UV–vis (MeOH) λmax: 344, 250, 210 nm; NMR data (1H: 500 MHz, DMSO-d6) comparable to the previously described spectral data [14][15]; HRESIMS m/z: [M + H]+ calcd for C47H62N3O9+, 812.4481; found, 812.4489; [M
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Published 11 Feb 2025

Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles

  • Yujun Pang,
  • Jinglan Yan,
  • Nawaf Al-Maharik,
  • Qian Zhang,
  • Zeguo Fang and
  • Dong Li

Beilstein J. Org. Chem. 2025, 21, 234–241, doi:10.3762/bjoc.21.15

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  • transformation (Table 1, entries 2 and 3), and PIDA was the most efficient promoter. Changing THF to other solvents, such as DCM, EtOH, DMF, CH3CN, EtOAc, or DMSO, resulted in a lower yield (Table 1, entries 4–9). Furthermore, variations in the amounts of PIDA or CF2HCOOH led to diminished yields (Table 1
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Published 30 Jan 2025

Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide

  • Marios Zingiridis,
  • Danae Papachristodoulou,
  • Despoina Menegaki,
  • Konstantinos G. Froudas and
  • Constantinos G. Neochoritis

Beilstein J. Org. Chem. 2025, 21, 217–225, doi:10.3762/bjoc.21.13

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  • pyrimidine scaffold. Representative fluorescence spectrum of compounds 5b (λex = 330 nm) and 6e (λex = 430 nm) at 0.2 M in DMSO. Molecular geometry observed within the crystal structure of compound 7b (CCDC 2376493). Strategies towards targeted adducts: A) Niementowski quinazoline synthesis utilizing
  • materials. The colored frames indicate the different scaffold types. Synthesis of N-substituted thienopyrimidones 5a–e by a Gewald three-component reaction employing 2-aminothiophenes 2a–e and formamide as C1 source. A characteristic fluorescence for compound 5a was reported (365 nm in DMSO). The reported
  • yield refers to the overall two-step synthesis. Synthesis of N-substituted quinolinopyrimidones 6a–e from 2-aminoindoles 3a–e and formamide as C1 source. A characteristic fluorescence for compound 6c was reported (365 nm in DMSO). The reported yields refer to the overall two-step synthesis. Synthesis of
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Published 24 Jan 2025

Quantifying the ability of the CF2H group as a hydrogen bond donor

  • Matthew E. Paolella,
  • Daniel S. Honeycutt,
  • Bradley M. Lipka,
  • Jacob M. Goldberg and
  • Fang Wang

Beilstein J. Org. Chem. 2025, 21, 189–199, doi:10.3762/bjoc.21.11

Graphical Abstract
  • by hydrogen bond acidity [47][48] which is derived from the 1H NMR chemical shift difference of a given proton in DMSO-d6 and CDCl3, the CF2H group is generally a stronger donor than the methyl group but substantially weaker than the OH or amide NH groups [19][20]. These results collectively indicate
  • method [19][20][47][48]. This convenient approach relies on comparing the 1H NMR chemical shift of a hydrogen bond donor in DMSO-d6 to that of it in CDCl3. The HB donor presumably interacts strongly with hydrogen-accepting DMSO [51], but barely with CDCl3, which has a weak hydrogen bond acceptance
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Published 20 Jan 2025

Emerging trends in the optimization of organic synthesis through high-throughput tools and machine learning

  • Pablo Quijano Velasco,
  • Kedar Hippalgaonkar and
  • Balamurugan Ramalingam

Beilstein J. Org. Chem. 2025, 21, 10–38, doi:10.3762/bjoc.21.3

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  • with feedback DOE facilitated the rapid identification of appropriate solvents. Notably, the use of DMSO, DMF, and pyridine led to an enhanced yield of the monoalkylated product. An experimental setup was developed for single-droplet studies of visible-light photoredox catalysis using an oscillatory
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Published 06 Jan 2025

Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade

  • Merve Yence,
  • Dilgam Ahmadli,
  • Damla Surmeli,
  • Umut Mert Karacaoğlu,
  • Sujit Pal and
  • Yunus Emre Türkmen

Beilstein J. Org. Chem. 2024, 20, 3290–3298, doi:10.3762/bjoc.20.273

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  • formation reaction. Pleasingly, benzo[j]fluoranthene 27 was obtained successfully via the Pd-catalyzed reaction of dibromonaphthalene 14 and naphthylboronic ester 26 in DMSO at 120 °C, albeit in a modest yield of 34%. A final basic hydrolysis of the acetoxy group furnished benzo[j]fluoranthene 23 bearing a
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Published 23 Dec 2024
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