Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

• Ritu Mamgain,
• Kokila Sakthivel and
• Fateh V. Singh

Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243

• assessed as inhibitors of galectin-9 and were found to exhibit selectivity and potency against galectin-9. In 2021, Chen and colleagues developed a method to synthesize naproxen-containing diaryliodonium salts 67 using naproxen methyl ester 65 and ArI(OH)OTs 66, activated by trimethylsilyl

• trifluoromethanesulfonate (TMSOTf). This synthesis was conducted in a mixture of 2,2,2-trifluoroethanol (TFE) and dichloromethane [78]. The synthesized naproxen-containing diaryliodonium salt 67 was further used to modify the aromatic ring of naproxen methyl ester 68 (Scheme 27). Various functionalization reactions which

• include arylation, iodination, alkynylation, thiophenolation, amination, and esterification, were carried out. Among these reactions, esterification was achieved in moderate yield under metal-free conditions by reacting the synthesized naproxen methyl ester (2-methoxyphenyl)iodonium

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

• Nian Li,
• Ruzal Sitdikov,
• Ajit Prabhakar Kale,
• Joost Steverlynck,
• Bo Li and
• Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

• methanol, equipped with a graphite anode and a platinum plate cathode, under a current of 10 mA at 60 °C for 3–20 hours. Several electrochemical LSF of pharmacologically active molecules were tested, including naproxen methyl ester, a derivative of aminoglutethimide, and paracetamol. The corresponding

• complex molecules, such as naproxen and cholesterol derivatives, demonstrated good functional group compatibility (Scheme 23a). In the same year, Wang and Huang group reported a similar approach using electrochemical methods to synthesize 3-selenylindoles via the cyclization of 2-ethynylanilines and

Direct synthesis of acyl fluorides from carboxylic acids using benzothiazolium reagents

• Lilian M. Maas,
• Alex Haswell,
• Rory Hughes and
• Matthew N. Hopkinson

Beilstein J. Org. Chem. 2024, 20, 921–930, doi:10.3762/bjoc.20.82

• % 19F NMR yields, respectively. Furthermore, the widely available drug molecules naproxen and ibuprofen could be efficiently converted into their acyl fluoride derivatives 2k and 2l in 97% and quantitative yields, respectively. To improve the practicality of the methodology and to avoid the often

Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis

• Nicoleta G. Hădărugă,
• Gabriela Popescu,
• Dina Gligor (Pane),
• Cristina L. Mitroi,
• Sorin M. Stanciu and
• Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

• , cyclosporine A and polyvinyl alcohol, ketoprofen and phospholipids, dihydroartemisinin and lecithin, cefixime and ʟ-arginine, flurbiprofen and naproxen/ketoprofen/ethenzamide [50][51][52][53][54][55][56][57][58][59]. Fourier-transform infrared spectroscopy (FTIR) is a very fast, nondestructive and cheap method

Synthesis of α-(perfluoroalkylsulfonyl)propiophenones: a new set of reagents for the light-mediated perfluoroalkylation of aromatics

• Durbis J. Castillo-Pazos,
• Juan D. Lasso and
• Chao-Jun Li

Beilstein J. Org. Chem. 2022, 18, 788–795, doi:10.3762/bjoc.18.79

• 12c in 68% isolated yield, but as tends to be the case for inactivated substrates, excess quantities of benzene (50% v/v) were required. Compounds containing esters such as methyl 3,4,5-trimethoxybenzoate and naproxen methyl ester were also tolerated and the desired products 13b and 14b were isolated

Recent advances in Cu-catalyzed C(sp³)–Si and C(sp³)–B bond formation

• Balaram S. Takale,
• Ruchita R. Thakore,
• Elham Etemadi-Davan and
• Bruce H. Lipshutz

Beilstein J. Org. Chem. 2020, 16, 691–737, doi:10.3762/bjoc.16.67

• either CuCl/quinoxP* or their in-house-developed chiral sulfoxide phosphine ligand (SOP). Excellent diastereo- and enantioselectivities were obtained. A gram scale synthesis of (S)-naproxen was also described as a “real world” application [106]. From previous findings involving trapping of a vinylarene

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

• Michael K. Bogdos,
• Emmanuel Pinard and
• John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

• 33c). Examples such as the synthesis of a modified structure of naproxen, starting from the methyl ester of the well-known NSAID, demonstrate the full power of the protocol for its use as a LSF tool. The mild conditions, selectivity on certain substrates and the great opportunity for diversification

• photocatalyst, under irradiation from blue LEDs and aerobic conditions (Scheme 34) [80]. The authors show a set of diverse molecules that underwent the transformation cleanly. The group again demonstrated the LSF applications by cyanating the methyl ester naproxen derivative 34a. In summary, organophotoredox

Exploring mechanochemistry to turn organic bio-relevant molecules into metal-organic frameworks: a short review

• Vânia André,
• Sílvia Quaresma,
• João Luís Ferreira da Silva and
• M. Teresa Duarte

Beilstein J. Org. Chem. 2017, 13, 2416–2427, doi:10.3762/bjoc.13.239

• RS-forms), salicylic acid [130] and naproxen using water as the grinding liquid [7]. With naproxen, LAG was also used to screen for hydrated forms of magnesium–naproxen by systematically varying the fraction of water in the LAG experiments [7]. Low, intermediate and high amounts of water as grinding

• ) fragment of the crystal structure of a mechanochemically obtained magnesium–ibuprofen complex; d) fragment of the crystal structure of a mechanochemically obtained magnesium–salicylate complex; e) screening for different hydrated forms of magnesium–naproxen BioMOFs by systematically varying the quantity of

• water in LAG reactions of MgO and (S)-naproxen. Reprinted with permission from [29], copyright 2012 the Royal Society of Chemistry. Mechanochemical reaction to form Cu3(BTC)2 and the structure of Cu3(BTC)2·(HKUST-1) as reported by Williams et al. [132]. Reprinted with permission from [131], copyright

Conjugate addition–enantioselective protonation reactions

• James P. Phelan and
• Jonathan A. Ellman

Beilstein J. Org. Chem. 2016, 12, 1203–1228, doi:10.3762/bjoc.12.116

• :36.5 to 67.5:32.5 er). To demonstrate the utility of the transformation, the sulfur–carbon bond of 26a was reduced using Raney nickel to access (S)-naproxen (27), an anti-inflammatory drug (Scheme 6b). Inspired by the work of Pracejus, Tan and colleagues applied their C2-symmetric guanidine catalyst 30

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

• Vito Rizzi,
• Sergio Matera,
• Paola Semeraro,
• Paola Fini and
• Pinalysa Cosma

Beilstein J. Org. Chem. 2016, 12, 549–563, doi:10.3762/bjoc.12.54

• . These results were further confirmed by other examples reported in literature, such as the effect on the indomethacin-related carbonyl band and the significant reduction of intensity of similar bands for naproxen in the presence of β-CD observed in [34]. More information was searched looking at the OH

Synthesis and characterization of pH responsive D-glucosamine based molecular gelators

• Navneet Goyal,
• Hari P. R. Mangunuru,
• Bargav Parikh,
• Sonu Shrestha and
• Guijun Wang

Beilstein J. Org. Chem. 2014, 10, 3111–3121, doi:10.3762/bjoc.10.328

• naproxen from the pH responsive gels were also analyzed under acidic and neutral conditions. Our findings are useful for the design of novel triggered release self-assembling systems and can provide an insight into the influence of the the structure on gelation. Keywords: glucosamine; hydrogelators

• ; naproxen; organogelator; pH responsive; self-assembly; Introduction Low molecular weight gelators (LMWGs) have drawn great attention over the past few decades due to the formation of supramolecular structures and their potential applications as advanced materials [1][2][3][4][5][6][7]. LMWGs are also

• anticipated that these types of gels may be useful for the controlled release of drugs or other agents under acidic conditions. We picked the nonsteroidal anti-inflammatory drug (NSAID) naproxen as an example and studied the release profile of the drug trapped in the gel matrix. To test the effectiveness of

Synthesis of modified cyclic and acyclic dextrins and comparison of their complexation ability

• Kata Tuza,
• László Jicsinszky,
• Tamás Sohajda,
• István Puskás and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 2836–2843, doi:10.3762/bjoc.10.301

• favorably cyclic conformation and this explains the weak complex formation contrary to the smaller-sized non-cyclic analogs (G3, G4 and G5) not showing any interaction. In another study of Bettinetti et al. G7 was found to wrap up naproxen, taking on a cyclic conformation and forming a ‘pseudo’ inclusion

Electrocarboxylation: towards sustainable and efficient synthesis of valuable carboxylic acids

• Roman Matthessen,
• Jan Fransaer,
• Koen Binnemans and
• Dirk E. De Vos

Beilstein J. Org. Chem. 2014, 10, 2484–2500, doi:10.3762/bjoc.10.260

• -methoxynaphthalene (AMN) can be converted to hydroxynaproxen (HN), a precursor of naproxen (Scheme 13) [85][86]. Although yields up to 90% were obtained in a 1 L flow reactor, the switch to a 75 L system was accompanied by leaks and instrument problems resulting in a low yield (58%) and current efficiency (30%) [86

• anode. The method appeared also suitable for the synthesis of other NSAIDs like naproxen, cicloprofen, isoprofen, flurbiprofen, fenoprofen and carprofen. The electrocarboxylation of aliphatic aldehydes was also patented, namely for the production of 2-hydroxy-4-methylmercaptobutyric acid (MHA) by

The conjugation of nonsteroidal anti-inflammatory drugs (NSAID) to small peptides for generating multifunctional supramolecular nanofibers/hydrogels

• Jiayang Li,
• Yi Kuang,
• Junfeng Shi,
• Yuan Gao,
• Jie Zhou and
• Bing Xu

Beilstein J. Org. Chem. 2013, 9, 908–917, doi:10.3762/bjoc.9.104

• covalent linkage of Phe–Phe and NSAIDs results in conjugates that self-assemble in water to form molecular nanofibers as the matrices of hydrogels. When the NSAID is naproxen (1), the resultant hydrogelator 1a forms a hydrogel at a critical concentration (cgc) of 0.2 wt % at pH 7.0. Hydrogelator 1a, also

• of small molecule hydrogels formed by NSAID derivatives [48][54][55][56] we intend to explore supramolecular hydrogels of other NSAIDs. Specifically, we use naproxen (denoted as Npx in this report), an over-the-counter NSAID, to generate a new hydrogelator 1a that only consists of naproxen and

• phosphatase and results in a hydrogel of 1d under physiological conditions. In addition to naproxen, we evaluate the abilities of other NSAIDs (Scheme 1) as building blocks of hydrogelators and find that the conjugates of FF and (R)-flurbiprofen (2), racemic flurbiprofen (3) or racemic ibuprofen (4) form