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Search for "mechanism" in Full Text gives 1826 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Microwave-enhanced additive-free C–H amination of benzoxazoles catalysed by supported copper

  • Andrei Paraschiv,
  • Valentina Maruzzo,
  • Filippo Pettazzi,
  • Stefano Magliocco,
  • Paolo Inaudi,
  • Daria Brambilla,
  • Gloria Berlier,
  • Giancarlo Cravotto and
  • Katia Martina

Beilstein J. Org. Chem. 2025, 21, 1462–1476, doi:10.3762/bjoc.21.108

Graphical Abstract
  • open derivative, and the subsequent ring oxidation upon closure (as shown in the mechanism in Scheme S1 (Supporting Information File 1), the reaction mixture may contain the desired 2-substituted benzoxazole 2a together with its open-form precursor 2a-o. The latter can be hydrolysed to give N
  • reaction conditions both in terms of temperature and time, as observed using a lower catalyst amount. This assumption was confirmed when the reaction was performed in a MW reactor under 5 bar of N2; in this environment, the copper catalyst cannot regenerate because of the absence of oxygen (see mechanism
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Published 15 Jul 2025

Wittig reaction of cyclobisbiphenylenecarbonyl

  • Taito Moribe,
  • Junichiro Hirano,
  • Hideaki Takano,
  • Hiroshi Shinokubo and
  • Norihito Fukui

Beilstein J. Org. Chem. 2025, 21, 1454–1461, doi:10.3762/bjoc.21.107

Graphical Abstract
  • absence of carbonyl groups in bis-olefin 5 has been corroborated by Fourier transform infrared (FTIR) spectroscopy (Figure S16 in Supporting Information File 1). Compound 4 could be generated through the reaction of compound 3 with phosphorus ylide. However, a reliable reaction mechanism remains unclear
  • . A tentative mechanism that may be plausible is shown in Supporting Information File 1, Figure S21, which consists of (1) the nucleophilic attack of methylenetriphenylphosphorane to the exo-methylene group of 3, (2) the intramolecular carbon–carbon-bond formation at the carbonyl group, and (3) the
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Published 14 Jul 2025

Advances in nitrogen-containing helicenes: synthesis, chiroptical properties, and optoelectronic applications

  • Meng Qiu,
  • Jing Du,
  • Nai-Te Yao,
  • Xin-Yue Wang and
  • Han-Yuan Gong

Beilstein J. Org. Chem. 2025, 21, 1422–1453, doi:10.3762/bjoc.21.106

Graphical Abstract
  • -containing hetero[5]- and [6]helicene-like structures 68a–g in high yields [82]. These compounds display diverse photophysical behaviors: compound 68d emits yellow fluorescence in both solution and solid state, exhibiting solvatofluorochromism due to a twisted intramolecular charge transfer (TICT) mechanism
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Published 11 Jul 2025

Tautomerism and switching in 7-hydroxy-8-(azophenyl)quinoline and similar compounds

  • Lidia Zaharieva,
  • Vera Deneva,
  • Fadhil S. Kamounah,
  • Nikolay Vassilev,
  • Ivan Angelov,
  • Michael Pittelkow and
  • Liudmil Antonov

Beilstein J. Org. Chem. 2025, 21, 1404–1421, doi:10.3762/bjoc.21.105

Graphical Abstract
  • . According to them neither 1 nor 2 is suitable for switching from E to K for couple of reasons. The most important one is the higher relative energy of K in respect of KK. This means that if KK is populated, according to the above described mechanism, the tautomeric proton cannot be released to K, i.e. the
  • presented as relative energies in kcal/mol. The values of the angles α and β (see also Scheme 2) are given in brackets (β is underlined). The asterisk indicates trans to cis isomerization via inversion mechanism [67]. In the excited state the relative energy is followed by the oscillator strength of the
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Published 10 Jul 2025

High-pressure activation for the solvent- and catalyst-free syntheses of heterocycles, pharmaceuticals and esters

  • Kelsey Plasse,
  • Valerie Wright,
  • Guoshu Xie,
  • R. Bernadett Vlocskó,
  • Alexander Lazarev and
  • Béla Török

Beilstein J. Org. Chem. 2025, 21, 1374–1387, doi:10.3762/bjoc.21.102

Graphical Abstract
  • synthesis is still in its infancy. Despite the recent advances [10][11], the HHP applications in this field are still being developed. The first HHP-assisted organic syntheses were reported in the 1970s [12][13]. Although the mechanism of how pressure enables reactions is not fully elucidated, there is a
  • full analysis can be obtained by also evaluating the activation volume (ΔV‡) data. Considering that all of the above studied reactions are multistep processes with several elementary steps, the determination of ΔV‡ requires a detailed theoretical reaction mechanism study that is beyond the scope of the
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Published 02 Jul 2025

Oxetanes: formation, reactivity and total syntheses of natural products

  • Peter Gabko,
  • Martin Kalník and
  • Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

Graphical Abstract
  • /RPC mechanism starts with a single-electron oxidation of the cobalt catalyst followed by a reaction with the siloxane to generate a cobalt–hydride complex. Subsequent hydride transfer to the alkene produces radical pair 23 which collapses to alkylcobalt intermediate 24. Another single-electron
  • -mediated intramolecular cross-couplings, 2-alkylideneoxetanes can also be accessed by formal [2 + 2] cycloadditions, which are discussed in chapter 1.3.2. 1.2 C–C Bond-forming cyclisations This relatively uncommon strategy is usually based on an ionic mechanism in which an SN2 substitution takes place
  • polysubstituted oxetanes 64 (Scheme 18) [57]. The mechanism is based on a 1,5-HAT/radical recombination sequence where the H-atom transfer is triggered by an S0 → T1 excitation of the starting allyl ether 63 using an iridium photosensitiser and blue light for irradiation. The method employs mild reaction
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Published 27 Jun 2025

Recent advances and future challenges in the bottom-up synthesis of azulene-embedded nanographenes

  • Bartłomiej Pigulski

Beilstein J. Org. Chem. 2025, 21, 1272–1305, doi:10.3762/bjoc.21.99

Graphical Abstract
  • of a naphthalene-bridged double [6]helicene (Scheme 6) [46]. Depending on the amount of DDQ used for oxidation, the yield of 36 reached up to 22%, while 37 was obtained in up to 27% yield. The proposed mechanism for the formation of 36 and 37 involves an arenium ion-mediated 1,2-phenyl shift followed
  • by a naphthalene-to-azulene rearrangement. The alternative radical cation mechanism has a higher energy barrier than the arenium cation-mediated reaction. Notably, only one of the pentagon–heptagon pairs exhibits an azulene-like electronic structure and aromaticity, as confirmed by the analysis of
  • mechanism and 1,2-phenyl shift. However, in this case, analysis of NICS values indicated that the azulene moiety does not exhibit aromatic character, and the electronic properties of the final molecules are primarily determined by the surrounding benzenoid rings. Mastalerz and co-workers reported the
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Published 26 Jun 2025

Recent advances in oxidative radical difunctionalization of N-arylacrylamides enabled by carbon radical reagents

  • Jiangfei Chen,
  • Yi-Lin Qu,
  • Ming Yuan,
  • Xiang-Mei Wu,
  • Heng-Pei Jiang,
  • Ying Fu and
  • Shengrong Guo

Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98

Graphical Abstract
  • -methylpiperidine, proved compatible with the reaction conditions, yielding the corresponding 3-(2-oxoethyl)indolin-2-ones 5a–g in 40–78% yields. Following a detailed investigation, a plausible mechanism was proposed, as illustrated in Scheme 3. Initially, TBHP undergoes cleavage by Fe2+ to generate a tert-butoxy
  • -free synthetic method for 3,3-disubstituted oxindoles via 1,2-alkylarylation of activated alkenes with alcohols [4]. N-Arylacrylamides and simple alcohols were employed as substrates, proceeding through an oxidative radical cyclization mechanism. The standard reaction conditions involved the use of an
  • demonstrated that both primary and secondary alcohols were compatible substrates (7a, 7f). The proposed reaction mechanism involves oxidative radical cyclization. Initially, TBHP undergoes homolytic cleavage to generate a tert-butoxy radical, which then forms an α-hydroxy carbon radical. This radical
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Published 24 Jun 2025

Synthesis of β-ketophosphonates through aerobic copper(II)-mediated phosphorylation of enol acetates

  • Alexander S. Budnikov,
  • Igor B. Krylov,
  • Fedor K. Monin,
  • Valentina M. Merkulova,
  • Alexey I. Ilovaisky,
  • Liu Yan,
  • Bing Yu and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2025, 21, 1192–1200, doi:10.3762/bjoc.21.96

Graphical Abstract
  • isolated in 77% yield (1.3 g, 4.61 mmol). In order to propose the reaction mechanism, control experiments were conducted (Scheme 4). The reaction is completely inhibited by the addition of (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) or BHT (Scheme 4, reaction 1). A BHT-adduct derived from a P-centered
  • radical was detected by HRMS, which supported a radical mechanism. Next, the influence of the atmosphere and the role of copper catalyst was evaluated (Scheme 4, reaction 2). Neither under argon nor under an oxygen atmosphere, the yield of 3a did not exceed 22%. However, employing 200 mol % of copper(II
  • results and previous reports on copper(II) mediated oxyphosphorylation reactions [42][44][46][51][53], a plausible reaction mechanism is proposed (Scheme 5). The discovered transformation is unlikely to proceed via only a single route (see control experiments in Scheme 4), and the generation of phosphorus
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Published 20 Jun 2025

Enhancing chemical synthesis planning: automated quantum mechanics-based regioselectivity prediction for C–H activation with directing groups

  • Julius Seumer,
  • Nicolai Ree and
  • Jan H. Jensen

Beilstein J. Org. Chem. 2025, 21, 1171–1182, doi:10.3762/bjoc.21.94

Graphical Abstract
  • , thereby dictating the site of C–H activation. Common DGs include unsaturated heteroatoms and alkenyl groups, which have proven effective in guiding the regioselectivity of these reactions [4]. Mechanistic studies with palladium(II) acetate (Pd(OAc)2) as catalyst support the following mechanism of C–H
  • activation, called concerted metal deprotonation (CMD) [5][6][7]. In a concerted mechanism, the Pd atom of the catalyst forms a sigma bond to an aromatic carbon, which increases the acidity of the adjacent (alpha) proton. This allows for the simultaneous abstraction of this proton by a carboxylate ligand. A
  • electrophilic aromatic substitution and a proton abstraction mechanism via CMD, where they calculated the relative energies of the intermediates. Using their workflow, they were able to predict correctly the regioselectivity for 18 tested substrates. The main limitation of this work is the computational cost
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Published 16 Jun 2025

A multicomponent reaction-initiated synthesis of imidazopyridine-fused isoquinolinones

  • Ashutosh Nath,
  • John Mark Awad and
  • Wei Zhang

Beilstein J. Org. Chem. 2025, 21, 1161–1169, doi:10.3762/bjoc.21.92

Graphical Abstract
  • (IMDA), and dehydrative re-aromatization reactions for the synthesis of imidazopyridine-fused isoquinolinones is developed. Gaussian computation analysis on the effect of the substitution groups for the IMDA reaction is performed to understand the reaction mechanism. Keywords: Groebke–Blackburn
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Published 13 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
  • Plasmodium parasites and recommends artemisinin combination therapy (ACT) for the treatment of both uncomplicated and severe malaria as a frontline treatment [1]. ACT includes the use of an artemisinin agent in concert with a partner drug (most often a quinoline drug), which possesses a different mechanism
  • -position (tele-substituted; Figure 1), distant from the halogen leaving group at position 5 [10]. A plausible reaction mechanism was proposed by Korsik et al. [10]. The antimalarial activity of series 4 triazolopyrazine scaffolds is generally reduced by substitution of an amine functionality at the 8
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Published 10 Jun 2025

Gold extraction at the molecular level using α- and β-cyclodextrins

  • Susana Santos Braga

Beilstein J. Org. Chem. 2025, 21, 1116–1125, doi:10.3762/bjoc.21.89

Graphical Abstract
  • . C skyblue, O red, Br brown, Au yellow. (c) Schematic illustration of the mechanism leading to precipitation (named “supramolecular polymerisation” by the authors) after adding various additives to the solution of β-CD and [AuBr4]− anions. Reproduced from [51] (© 2023 H. Wu et al., published by
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Published 06 Jun 2025

Salen–scandium(III) complex-catalyzed asymmetric (3 + 2) annulation of aziridines and aldehydes

  • Linqiang Wang and
  • Jiaxi Xu

Beilstein J. Org. Chem. 2025, 21, 1087–1094, doi:10.3762/bjoc.21.86

Graphical Abstract
  • enantioselectivities and high diastereoselectivities. A reasonable reaction mechanism was proposed and rationalized the experimental results. Keywords: aldehyde; annulation; aziridine; oxazolidine; ring expansion; scandium triflate; Introduction Oxazolidine derivatives are an important class of nitrogen and oxygen
  • uses readily available components. On the basis of the experimental results and a previous report [16], a possible reaction mechanism is presented in Scheme 3. The catalyst (Cat) is first generated from salen L1 and Sc(OTf)3. Aziridines 1 coordinate to the Sc ion in the catalyst with their two
  • functionalized oxazolidine derivatives in moderate to good yields and good to excellent enantioselectivities and high diastereoselectivities. The stereocontrol was rationalized in the proposed reaction mechanism. Experimental Unless otherwise noted, all materials were purchased from commercial suppliers. Toluene
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Published 28 May 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

Graphical Abstract
  • –380 via an α-borylation–protodeborylaton mechanism involving intermediates 381 and 382 (Scheme 83A) [141]. On the one hand, Vilotijevic and co-workers (2021) reported a phosphine-mediated partial hydrogenation of conjugated alkynes using water as the hydrogen source to obtain the corresponding cis
  • migratory insertion (407) (Scheme 86A) [145]. On the other hand, Werner and Liu (2020) reported a Mn-catalyzed coupling of alcohols and phosphorus ylide 408 to afford the corresponding E-isomers of cinnamate esters 409–411 via an acceptorless dehydrogenative coupling mechanism (Scheme 86B) [146]. In
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Published 28 May 2025

Pd-Catalyzed asymmetric allylic amination with isatin using a P,olefin-type chiral ligand with C–N bond axial chirality

  • Natsume Akimoto,
  • Kaho Takaya,
  • Yoshio Kasashima,
  • Kohei Watanabe,
  • Yasushi Yoshida and
  • Takashi Mino

Beilstein J. Org. Chem. 2025, 21, 1018–1023, doi:10.3762/bjoc.21.83

Graphical Abstract
  • -catalyzed asymmetric allylic amination of allyl esters with isatin using (aR)-(−)-6 possesses an S-configuration. This stereochemical outcome follows the same reaction mechanism as the Pd-catalyzed asymmetric allylic substitution of allyl esters with indoles using (aR)-(−)-6 [31]. To explore further
  • allylic amination of acetate 12 with isatin (11a).a Supporting Information Data of thermal racemization of 7, DFT calculations for investigating racemization mechanism of 7, general methods and materials, experimental procedures and characterization data, 1H, 13C and 31P NMR spectra for 9 and 10, 1H, 13C
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Published 23 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

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  • examples of amino-sulfonoxylations using tethered nitreniums. Putative reaction mechanism. (A) Scale-up and (B) applications. Optimization results. Structure–reactivity relationship with nitrenium tethers. Examination of sulfonic acid scope. Substrate scope exploration with an emphasis on stereocontrol and
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Published 19 May 2025

Silver(I) triflate-catalyzed post-Ugi synthesis of pyrazolodiazepines

  • Muhammad Hasan,
  • Anatoly A. Peshkov,
  • Syed Anis Ali Shah,
  • Andrey Belyaev,
  • Chang-Keun Lim,
  • Shunyi Wang and
  • Vsevolod A. Peshkov

Beilstein J. Org. Chem. 2025, 21, 915–925, doi:10.3762/bjoc.21.74

Graphical Abstract
  • was not isolated. Instead, the reaction mixture was concentrated and directly subjected to the subsequent heteroannulation step. This approach proved to be feasible, affording the model pyrazolo[1,5-a][1,4]diazepine 16a in 65% overall yield over two steps (Scheme 4). The tentative mechanism for the
  • conducted in screw cap vials at 90 °C for 7 hours and isolated yields are reported. aConducted on a 3.5 mmol scale. bConducted on a 0.5 mmol scale. Telescope procedure for the synthesis of 16a. Tentative mechanism for the silver-catalyzed heteroannulation. Reductive post-assembly modifications of the
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Published 08 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

Graphical Abstract
  • environment around the copper center disfavors a direct interaction with nucleophilic alkyl radicals. Instead, the reaction proceeds via an outer-sphere mechanism, where the alkyl radical reacts with the copper-activated C=N unsaturated bond, enabling stereocontrolled C(sp3)–C(sp3) coupling. In contrast, with
  • -29. This intermediate undergoes reductive elimination via an inner-sphere mechanism to generate the C(sp3)–N-coupled chiral product 22. Notably, benzoic acid acts as a critical additive, likely by stabilizing key intermediates and modulating the steric/electronic environment for enhanced
  • -methylacryloylbenzamides, and 2-iodobiphenyls – thereby selectively synthesizing silacyclic compounds with varying ring sizes, including ten-membered, seven-membered, and five-membered rings. Mechanism (Scheme 15): Substrate 53 undergoes oxidative addition with Pd(0), followed by intramolecular carbopalladation to form
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Published 07 May 2025

Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes

  • Patricia Gómez-Roibás,
  • Andrea Chaves-Pouso and
  • Martín Fañanás-Mastral

Beilstein J. Org. Chem. 2025, 21, 877–883, doi:10.3762/bjoc.21.71

Graphical Abstract
  • not result in the formation of the dimerization product and complex mixtures of products were observed in these cases. To gather insight into the reaction mechanism, several control experiments were performed (Scheme 3). We first observed that the reaction does not take place in the absence of B2pin2
  • mechanism for the copper-catalyzed diastereoselective dimerization of 4,4-dichoro-2-butenoic acid derivatives (Scheme 4). Initially, the LCu–pin complex generated through reaction between LCu–Ot-Bu and B2pin2 undergoes coordination and regioselective insertion into 1 giving rise to β-borylated organocopper
  • mechanism for the Cu-catalyzed dimerization of 4,4-dichoro-2-butenoic acid derivatives. a) KOt-Bu-mediated intramolecular cyclization of 9. b) Direct formation of cyclopropane 20 from gem-dichloride 5 using KOt-Bu as base. Optimization studies. Synthesis of densely functionalized (2,2-dichlorovinyl
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Published 05 May 2025

Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic esters

  • Lewis McGhie,
  • Hannah M. Kortman,
  • Jenna Rumpf,
  • Peter H. Seeberger and
  • John J. Molloy

Beilstein J. Org. Chem. 2025, 21, 854–863, doi:10.3762/bjoc.21.69

Graphical Abstract
  • state catalyst are not operational (see Supporting Information File 1 for full details), providing support for an EnT mechanism, while exposing the Z-isomer (Z)-1a to the model reaction conditions, led to the generation of a similar photostationary state equilibrium of isomers, characteristic of an EnT
  • as an operational mechanism. While intermolecular alkene quenching to enable [2 + 2] cycloaddition was inefficient, presumably due to poor substrate lifetime, intramolecular [2 + 2] reactivity with both acrylates and alkenylboronic esters was effective. The small 3D, boron-containing fragments could
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Published 30 Apr 2025

Chitosan-supported CuI-catalyzed cascade reaction of 2-halobenzoic acids and amidines for the synthesis of quinazolinones

  • Xuhong Zhao,
  • Weishuang Li,
  • Mengli Yang,
  • Bojie Li,
  • Yaoyao Zhang,
  • Lizhen Huang and
  • Lei Zhu

Beilstein J. Org. Chem. 2025, 21, 839–844, doi:10.3762/bjoc.21.67

Graphical Abstract
  • higher reactivity than 2-bromobenzoic acid derivatives. Based on previously reported literature [7][13], a mechanism for the copper-catalyzed formation of quinazolinones is proposed in Scheme 3. Initially, the 2-halobenzoic acid 1 coordinates with CS@CuI to form intermediate I in the presence of Na2CO3
  • (0.2 mmol), amidine hydrochloride 2 (0.3 mmol, 1.5 equiv), CS@CuI (5.0 mol %), Na2CO3 (1.25 mmol, 2.5 equiv), iPrOH/H2O 9:1 (2.0 mL), 90 °C, 12 h, argon atmosphere. Proposed mechanism for the CS@CuI-catalyzed synthesis of quinazolinones. Scaling-up experiment (a) and recyclability of CS@CuI (b
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Published 28 Apr 2025

Substituent effects in N-acetylated phenylazopyrazole photoswitches

  • Radek Tovtik,
  • Dennis Marzin,
  • Pia Weigel,
  • Stefano Crespi and
  • Nadja A. Simeth

Beilstein J. Org. Chem. 2025, 21, 830–838, doi:10.3762/bjoc.21.66

Graphical Abstract
  • mechanism is one of the fastest relaxation mechanism for heterocyclic azobenzenes (typically for most of the azo dyes [45]). However, the nature of the mechanism is still a matter of current debate, and additional factors, such as the presence of tautomerizable groups [46][47], and the involvement of the
  • triplet state [48], appear to play a role. Specifically, the rotation mechanism does not explain the low activation entropy observed in azobenzene systems [49] sparking new discussions on the possibility of alternative isomerization pathways [34]. Recently, Reimann et al. computationally showed that the
  • involvement of a triplet state mechanism, which crosses the transition state for the Z→E relaxation, could explain the low values of the activation entropy. The same authors also showed experimental evidence for this proposal by an external heavy atom effect on Z→E isomerization. To understand the thermal Z→E
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Published 25 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
  • active site of enzyme iNOS. Synthesis of 4-[1-(4-methoxybenzyl)amino]ethylidene-1,5-disubstituted pyrrolidine-2,3-diones 3a–e. Synthesis of 4-(1-methylamino)ethylidene-1,5-disubstituted pyrrolidine-2,3-diones 5a–e. Proposed mechanism for the reaction between 4-[1-(4-methoxybenzyl)amino]ethylidene-1,5
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Published 24 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
  • 98% yield. Ortho-bromoaryl-substituted nitrile 3m also underwent tandem amidation and copper-catalyzed cyclization, efficiently producing lactam 9 in a 98% yield. Scheme 7 illustrates a plausible reaction mechanism based on previous studies [34]. The process begins with the formation of NHC–copper
  • conditions: allene 4 (0.3 mmol), (iBu)2Al-H (0.3 mmol), IPrCuCl (5 mol %), TsCN (0.25 mmol), THF (0.2 M), under N2. The yields of the isolated products are given. Gram scale reaction. Synthetic applications. Proposed mechanism. Supporting Information Supporting Information File 40: General information
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Published 17 Apr 2025
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