Fe-catalyzed efficient synthesis of 2,4- and 4-substituted quinolines via C(sp²)–C(sp²) bond scission of styrenes

• Prafull A. Jagtap,
• Manish M. Petkar,
• Vaishnavi R. Sawant and
• Bhalchandra M. Bhanage

Beilstein J. Org. Chem. 2025, 21, 1799–1807, doi:10.3762/bjoc.21.142

• 26% yield. Then, in reaction 3, a one-pot, two-step reaction involving phenylglyoxalic acid (2aa) was carried out. In step 1, compounds 1a and 2aa were stirred at room temperature for 5 minutes in the presence of a catalyst and an additive. Subsequently, in step 2, styrene (2a) was added, and the

Unique halogen–π association detected in single crystals of C–N atropisomeric N-(2-halophenyl)quinolin-2-one derivatives and the thione analogue

• Mai Uchibori,
• Nanami Murate,
• Kanako Shima,
• Tatsunori Sakagami,
• Ko Kanehisa,
• Gary James Richards,
• Akiko Hori and
• Osamu Kitagawa

Beilstein J. Org. Chem. 2025, 21, 1748–1756, doi:10.3762/bjoc.21.138

• vapour diffusion of hexane into a methanol solution of the compound at room temperature) and their X-ray crystal structural analyses were performed (Figure 2) [33]. In the crystals of rac-1a, a π-type intermolecular interaction between the bromine atom and the benzene ring of the quinolinone was found

• observed in the crystals of optically pure forms (P)-1a,b (Figure 3, single crystals of (P)-1a,b were obtained by vapour diffusion of hexane into a methanol solution of the compound at room temperature) [34]. Meanwhile, the halogen atoms in (P)-1a,b were found to interact with the C4 atom on the lactam

• racemic quinolinones rac-1 in Figure 2 (single crystals of rac-2a were obtained from slow evaporation of hexane/methanol (1:1) mixture at room temperature) [37]. That is, in contrast to rac-1, in which homochiral layered polymer chains were formed, crystallization of quinoline-2-thione rac-2a led to the

Convenient alternative synthesis of the Malassezia-derived virulence factor malassezione and related compounds

• Karu Ramesh and
• Stephen L. Bearne

Beilstein J. Org. Chem. 2025, 21, 1730–1736, doi:10.3762/bjoc.21.135

• are uncorrected. tert-Butyl 3-(2-methoxy-2-oxoethyl)-1H-indole-1-carboxylate (21). A solution of indol-3-yl acetic acid (20, 5.1 g, 29.0 mmol, 1.0 equiv) in dry MeOH (200 mL) was cooled to 0 °C, and SOCl2 (10.5 mL, 145 mmol, 5.0 equiv) was added slowly. After stirring for 12 h at room temperature, the

• DMAP (0.63 g, 5.2 mmol, 0.2 equiv) were added [32]. The mixture was stirred for 2 h at room temperature after which the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (250 mL) and subsequently washed with saturated aqueous NH4Cl (150 mL), saturated aqueous NaHCO3 (150 mL

• , 3 equiv) in H2O (250 mL) was added to a solution of 21 (5.0 g, 17.2 mmol, 1.0 equiv) in THF (300 mL) and MeOH (150 mL). After stirring for 18 h at room temperature, the mixture was concentrated in vacuo and a 10% aqueous solution of citric acid (100 mL) was added. The aqueous layer was extracted

Synthesis of optically active folded cyclic dimers and trimers

• Ena Kumamoto,
• Kana Ogawa,
• Kazunori Okamoto and
• Yasuhiro Morisaki

Beilstein J. Org. Chem. 2025, 21, 1603–1612, doi:10.3762/bjoc.21.124

• samples were analyzed in CHCl3 at room temperature. Photoluminescence (PL) spectra were recorded on a JASCO FP-8500 spectrofluorometer, and samples were analyzed in CHCl3 at room temperature. Absolute PL quantum efficiency was calculated on a JASCO FP-8500 with an ILF-835 integrating sphere. The PL

• with CHCl3 as a solvent at room temperature. Circularly polarized luminescence (CPL) spectra were recorded on a JASCO CPL-300 with CHCl3 as a solvent at room temperature. Materials Commercially available compounds used without purification are as follows: Pd2(dba)3, SPhos (2-dicyclohexylphosphino-2',6

• 16 h. After the reaction mixture was cooled to room temperature, the solvent was removed with a rotary evaporator. The residue was purified by column chromatography on SiO2 (CHCl3/hexane = 1/4 v/v as an eluent) and by recyclable HPLC (CH2Cl2 as an eluent) to afford (Sp)-3 (24.6 mg, 0.031 mmol, 39

Chemical synthesis of glycan motifs from the antitumor agent PI-88 through an orthogonal one-pot glycosylation strategy

• Shaokang Yang,
• Xingchun Sun,
• Hanyingzi Fan and
• Guozhi Xiao

Beilstein J. Org. Chem. 2025, 21, 1587–1594, doi:10.3762/bjoc.21.122

• in mannosyl PVB 8 (1.0 equiv) in the presence of TMSOTf as catalyst proceeded smoothly at 0 °C to room temperature, affording the α-Man-(1→3)-Man PVB disaccharide. The further coupling of the above PVB disaccharide with the poorly reactive 2-OH in mannoside 9 (0.9 equiv) under activation with NIS and

• TMSOTf at 0 °C to room temperature, successfully furnished the desired α-Man-(1→3)-α-Man-(1→3)-α-Man trisaccharide 10 in 87% yield in a one pot manner. Removal of TBDPS group in 10 with 70% HF·pyridine and subsequent phosphitylation of the resulting free alcohol with phosphoramidite 11 provided the

• all Bz groups with 1 M NaOH (dioxane/MeOH/H2O, room temperature). The monophosphorylated trisaccharide 1 was obtained in 60% overall yield over two steps from 12 after purification over a SephadexTM LH-20 column. It was noted that the switch of deprotection sequences (first Bz groups, second Bn and

Thermodynamic equilibrium between locally excited and charge transfer states in perylene–phenothiazine dyads

• Issei Fukunaga,
• Shunsuke Kobashi,
• Yuki Nagai,
• Hiroki Horita,
• Hiromitsu Maeda and
• Yoichi Kobayashi

Beilstein J. Org. Chem. 2025, 21, 1577–1586, doi:10.3762/bjoc.21.121

• the degree of electronic interaction between the donor PTZ and acceptor Pe moieties, as indicated by the decreased overlap between HOMO and LUMO. UV–vis absorption spectra of the Pe–PTZ derivatives were recorded in benzene at room temperature (Figure 3a). All compounds exhibited characteristic

• phenothiazine derivative, 12-phenyl-12H-benzo[a]phenothiazine, in toluene at room temperature has been estimated to be 28 ps (with an additional minor 0.7 ps component attributed to small-scale structural changes) [17]. It is also noted that the relaxation dynamics depend on the molecular structure and the

• -31+G(d,p)//B3LYP/6-31+G(d,p) level of theory. Steady-state (a) absorption and (b) emission spectra of Pe–PTZ, Pe–PTZ(TPA), Pe–PTZ(TPA)2, and Pe–Ph–PTZ(TPA)2 in benzene at room temperature. The excitation wavelength was 420 nm for Pe–PTZ, Pe–PTZ(TPA)2, and Pe–Ph–PTZ(TPA)2, and 415 nm for Pe–PTZ(TPA

Synthesis of an aza[5]helicene-incorporated macrocyclic heteroarene via oxidation of an o-phenylene-pyrrole-thiophene icosamer

• Yusuke Matsuo,
• Aoi Nakagawa,
• Shu Seki and
• Takayuki Tanaka

Beilstein J. Org. Chem. 2025, 21, 1561–1567, doi:10.3762/bjoc.21.119

• acyclic heteroaromatics [26][27]. Thus, to a solution of 4 in CH2Cl2 was added 15 equivalents of PIFA at −78 °C and stirred for 3 h. The mixture was then allowed to warm to room temperature to give a dark solution. The system was worked-up with NaBH4/MeOH for 10 minutes followed by extraction with CH2Cl2

• and evaporation of the solvent to afford a crude product, which was recrystallized from THF to give 5 in 58% yield. Due to its poor solubility in common organic solvents, the 1H NMR spectrum could only be recorded in DMSO. At room temperature, the 1H NMR spectrum in DMSO-d6 exhibited broad signals in

• at 399 nm (Figure 5b). A broad emission was observed at 528 nm, resulting in a relatively large Stokes shift of 6100 cm−1, which can be attributed to the structural relaxation in the excited state, as inferred by the observed broad 1H NMR spectrum at room temperature. Due to the thermal energy loss

Facile synthesis of hydantoin/1,2,4-oxadiazoline spiro-compounds via 1,3-dipolar cycloaddition of nitrile oxides to 5-iminohydantoins

• Juliana V. Petrova,
• Varvara T. Tkachenko,
• Victor A. Tafeenko,
• Anna S. Pestretsova,
• Vadim S. Pokrovsky,
• Maxim E. Kukushkin and
• Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 1552–1560, doi:10.3762/bjoc.21.118

• decomposing even at room temperature. Taking these into account, we have synthesized compound 5c using an alternative route starting from the chloro oxime 4a and 5-iminothiohydantoin 2j (Scheme 4), obtained similarly to other dipolarophiles [22]. The total yield of the product 5c in this case turned out to be

• stirred. After that, the reaction mixture was left to stir in the ice bath for 24 hours, allowing it to slowly reach room temperature. Diffusion mixing technique: A small vial (15 mL volume, diameter 1.3 cm) equipped with a magnetic stirring bar was charged with a mixture of dipolarophile 2 (1 equiv

• , 0.150 mmol) and hydroxyimidoyl chloride 4 (1.1 equiv, 0.165 mol) in 4.5 mL of DCM and then placed in larger vial (50 mL volume, diameter 3.5 cm) containing TEA (35.85 mmol, 5 mL). The outer vial was tightly closed with a lid and the reaction mixture was stirred at room temperature for 24 h. In both

Ambident reactivity of enolizable 5-mercapto-1H-tetrazoles in trapping reactions with in situ-generated thiocarbonyl S-methanides derived from sterically crowded cycloaliphatic thioketones

• Grzegorz Mlostoń,
• Małgorzata Celeda,
• Marcin Palusiak,
• Heinz Heimgartner,
• Marta Denel-Bobrowska and
• Agnieszka B. Olejniczak

Beilstein J. Org. Chem. 2025, 21, 1508–1519, doi:10.3762/bjoc.21.113

• stable 9 into the more stable 10 was observed in some cases (derived from 1c) in the CDCl3 solution at room temperature. Therefore, it seems likely that the first step of the reaction is the N–H insertion process. The compositions of the obtained crude mixtures suggest that the final addition step

• the sterically most hindered dispiro-cyclohexyl-substituted thiocarbonyl S-methanide 2d. Notably, in some cases spontaneous isomerization of the generally less stable thioaminals 9 in CDCl3 solution at room temperature was also observed. It seems likely that this isomerization follows an

Highly distinguishable isomeric states of a tripodal arylazopyrazole derivative on graphite through electron/hole-induced switching at ambient conditions

• Himani Malik,
• Sudha Devi,
• Debapriya Gupta,
• Ankit Kumar Gaur,
• Sugumar Venkataramani and
• Thiruvancheril G. Gopakumar

Beilstein J. Org. Chem. 2025, 21, 1496–1507, doi:10.3762/bjoc.21.112

• isomer of azobenzene (AB) is a few days. Arylazopyrazole-based molecular switches are one of the profoundly explored systems in recent times due to their superior bidirectional photoswitching and long half-life (over a thousand days at room temperature) of Z isomers. Herein, we utilize an efficient solid

• barrier and the long lifetime of the non-equilibrium states are at the origin of their remarkable stability at room temperature. The remarkable stability of the states at ambient conditions provides an opportunity to use a single FNAAP molecule as an 8-bit operation. We propose to switch the molecule

Photoredox-catalyzed arylation of isonitriles by diaryliodonium salts towards benzamides

• Nadezhda M. Metalnikova,
• Nikita S. Antonkin,
• Tuan K. Nguyen,
• Natalia S. Soldatova,
• Alexander V. Nyuchev,
• Mikhail A. Kinzhalov and
• Pavel S. Postnikov

Beilstein J. Org. Chem. 2025, 21, 1480–1488, doi:10.3762/bjoc.21.110

• . Finally, control experiments without irradiation gave only traces of the benzamide 2aa showing no activation by the Ru complex at room temperature (Table 1, entry 24). An experiment conducted under an air atmosphere yielded only 9% of 2aa (Table 1, entry 25) indicating that the presence of atmospheric

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

• in the literature [62][63]. The suspension was stirred magnetically for 6 hours at room temperature, resulting in the formation of a blue-coloured catalyst. We aimed to vary the amount of copper loaded onto the silica surface to achieve different catalyst loadings (Cu wt %) and compared their

• -aminopropyltriethoxysilane (2 mmol) in toluene (10 mL). The suspension was sonicated for 2 h in an US bath (Power 200 W, Frequency 80 kHz). The resulting silica was then filtered, washed with toluene and chloroform, and dried under vacuum at room temperature for 12 hours. The derivatised silica was characterised by means of

• TGA and FTIR. Si-MonoAm (200 mg) and 16 mg of Cu(I)Cl were dispersed in 4 mL of THF. The mixture was stirred at room temperature for 4 hours, filtered under reduced pressure, and the powder was washed with THF and CHCl3. The resulting product was then kept in a desiccator overnight and fully

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

• of 1.5 kcal mol−1 and 3.2 cal K−1 mol−1, respectively (Figure S26 in Supporting Information File 1). These physical parameters give a free energy ΔG298 of 0.55 kcal mol−1, indicating approximately a 2:5 ratio of figure-eight and bathtub conformations at room temperature. Mono-olefin 3 exhibited

• slightly preferred at room temperature with approximately a 3:2 ratio of figure-eight and bathtub conformations. We have also estimated the activation barriers of the interconversion of 3 and 5 between the figure-eight and bathtub conformations by measuring VT 1H NMR spectra in toluene-d8 because the

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

• core [17]. Compared to 4a, compound 4b exhibits bathochromic shifts of 12 nm in absorption and 45 nm in emission, as well as a higher ΦF (0.75 vs 0.68). Both isomers display TADF at room temperature and phosphorescence at 77 K. Notably, 4a demonstrates a long-lived red afterglow persisting for up to 30

• showed more intense phosphorescence and an extended emission lifetime in dilute solution. Notably, it demonstrated room-temperature dual-emission CPL originating from both prompt fluorescence and long-lived phosphorescence, a rare feature in helicene systems. In a subsequent study, the same group

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

• number of industrially used azo dyes [1][3] and therefore its tautomerism is studied in details. The existing experimental data for low polar solvents (cyclohexane and tetrachloromethane) indicate a ΔG value of around 0.4 kcal/mol [53] at room temperature, which gives a prevalence of the E-tautomer (a

• makes possible to analyze the tautomerism in 1 as a function of (E+KE) and KK. The NMR spectra of 1 in acetonitrile-d3 are in agreement with the above analysis of tautomeric equilibration based on theoretical calculations and UV spectra. At room temperature the proton signals are very broad and

• agreement with other integrals in the proton spectrum. This means that at 243 K the mixture 1E+1KE is still dominating, but the content of 1KK slightly increases comparing to room temperature. This is not surprising bearing in mind that in the case of compound 3 the cooling in non-protic solvents (i.e

Reactions of acryl thioamides with iminoiodinanes as a one-step synthesis of N-sulfonyl-2,3-dihydro-1,2-thiazoles

• Vladimir G. Ilkin,
• Pavel S. Silaichev,
• Valeriy O. Filimonov,
• Tetyana V. Beryozkina,
• Margarita D. Likhacheva,
• Pavel A. Slepukhin,
• Wim Dehaen and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2025, 21, 1397–1403, doi:10.3762/bjoc.21.104

• expectations were not fulfilled. The exception is the data from entry 7 (Table 1), where the yield of compound 3aa was 78%. Thus, the conditions described in entry 7 (absence of a catalyst, use of 1.5 equiv of PhINTs 2a and dichloromethane (DCM) as a solvent at room temperature for 10 min) are optimal and were

• iodonium salts. The search for optimal conditions for the process has been carried out. The optimized reaction found to proceed in the absence of metal catalysts, using 1.5 equiv of the iodonium salt at room temperature in DCM. Using the optimized procedure, a library of 31 novel 2,3-dihydro-1,2-thiazoles

• thioamides 1h,i,k,n,o,s,t,v,w,y,z (general procedure). A mixture of the corresponding thioacetamide (1.0 equiv), aldehyde (1.1–4.0 equiv) and DBU (0.1 equiv or 1.0 equiv for 1h,o) in ethanol was stirred for 2–23 h at room temperature. For thioamide 1i, the reaction time was 96 h at 80 °C. The formed

N-Salicyl-amino acid derivatives with antiparasitic activity from Pseudomonas sp. UIAU-6B

• Joy E. Rajakulendran,
• Emmanuel Tope Oluwabusola,
• Michela Cerone,
• Terry K. Smith,
• Olusoji O. Adebisi,
• Adefolalu Adedotun,
• Gagan Preet,
• Sylvia Soldatou,
• Hai Deng,
• Rainer Ebel and
• Marcel Jaspars

Beilstein J. Org. Chem. 2025, 21, 1388–1396, doi:10.3762/bjoc.21.103

• (3 and 4) isolated alongside three known compounds, pseudomonine (5), pseudomonin B (6) and salicylic acid (7) [15] from the Pseudomonas sp. UIAU-6B strain by altering the fermentation conditions using an open system shaker at room temperature [16][17][18]. Results and Discussion The bacterial strain

• Pseudomonas sp. UIAU-6B was investigated by varying the temperature of the culture to elicit production of secondary metabolites after our previous work on the strain [15]. A small-scale culture of the strain (50 mL of SGG medium) shaken at 160 rpm in an open system shaker at room temperature yielded 0.008 g

• previously isolated pseudomonine [15]. This resulted in the decision to upscale the bacterial strain at room temperature in an open orbital shaker. The large crude extract (7.5 g) was subjected to Kupchan solvent partitioning followed by medium pressure liquid chromatography (MPLC) and subsequently

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

• -phenylenediamine and acetone was selected as a model reaction. The optimization of the reaction conditions is summarized in Table 1. All reactions were carried out at room temperature without involving any catalyst or additional solvent. While o-phenylenediamine is solid, it dissolves well in the reactant acetone

• subjected to those conditions to provide a representative scope of the reactions and the results are summarized in Scheme 2. For comparison, the yields obtained under ambient pressure (1 bar) are provided in parentheses. The data show that the reactions readily occur at room temperature providing good

• illustrate that HHP provides some advantage in both reactions, more evident in the case of OH acylation. The NH2 acylation occurred much more rapidly in 10 s at room temperature, while also generating the product nearly quantitatively. The OH group is significantly less reactive under such conditions

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

• and colleagues published a one-step synthesis of spirooxindole 2,2-disubstituted oxetanes 11 via an unprecedented addition/substitution cascade (Scheme 4) [39]. The protocol reacts readily available 3-hydroxyindolinones 9 with phenyl vinyl selenone (10) in aqueous KOH at room temperature and gives

• promoted by visible light at room temperature, requires no protecting atmosphere or additives, and the resulting polysubstituted oxetanes are obtained in moderate to good yields. Additional advantages include scalability and high chemoselectivity as various functional groups were tolerated, including

• oxetane sulphonyl fluorides can be conveniently prepared in 4 steps from 3-oxetanone and are sufficiently stable at room temperature and to air/moisture. The coupling proceeds upon gentle heating in the presence of K2CO3 as the only additive and affords the aminooxetanes in high yields, even for

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

• amount of Bu4NPF6 as the supporting electrolyte in a MeOH/TFE 11:1 (v/v) co-solvent mixture under blue LED irradiation at a constant current of 1.5 mA for 12 hours at room temperature. A wide range of substrates exhibited good functional group tolerance, with 3-homoallylquinazolin-4-ones bearing electron

• particularly noteworthy for its use at room temperature, requiring no transition metals, photocatalysts, or additives. Notably, Umemoto's reagent served as the trifluoromethyl source, and the reaction was facilitated under blue LED irradiation, achieving good to excellent yields. Moreover, this approach

• (4CzIPN), leading to either the reduction of sulfoxonium ylides to hydrocarbons or their participation in radical coupling with alkenes for carboarylation reactions. The reactions were carried out under mild, room temperature conditions using a DCM/H2O 1:2 solvent system. Various reaction conditions were

Optimized synthesis of aroyl-S,N-ketene acetals by omission of solubilizing alcohol cosolvents

• Julius Krenzer and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2025, 21, 1201–1206, doi:10.3762/bjoc.21.97

• -N-benzylbenzothiazolium salts in 1,4-dioxane at room temperature in short reaction time in 20–99% yield. This protocol represents a considerable improvement over the standard synthesis in 1,4-dioxane/ethanol mixtures at elevated temperatures. Keywords: aroyl chlorides; aroyl-S,N-ketene acetals

• , kinetic control is warranted by conducting the condensation synthesis at room temperature for only short reaction times. Furthermore, 2-MeTHF was successfully implemented as a sustainable alternative to 1,4-dioxane. This modified protocol is clearly superior to the initial protocol (in 1,4-dioxane/ethanol

• ) were placed in a sintered, dry screw-cap Schlenk-tube under nitrogen atmosphere and dissolved in dry 1,4-dioxane (30 mL). Triethylamine (1.52 mL, 11.0 mmol, 2.20 equiv) was added to the reaction mixture and the solution was stirred for 1 h at room temperature. The crude product was absorbed onto Celite

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

• stirred for 3 hours at 70 °C under air (air condenser) and then cooled to room temperature, and rotary-evaporated under reduced pressure. An additional evaporation step using a rotary vane pump (0.5 mmHg) at 80 °C was made for the evaporation of phosphite excess. The residue was isolated by column

Selective monoformylation of naphthalene-fused propellanes for methylene-alternating copolymers

• Kenichi Kato,
• Tatsuki Hiroi,
• Seina Okada,
• Shunsuke Ohtani and
• Tomoki Ogoshi

Beilstein J. Org. Chem. 2025, 21, 1183–1191, doi:10.3762/bjoc.21.95

• ) [55][56][63][64][65][66] yielded the monoformyl product [4.3.3]_CHO, in a selective manner (Table 1, entry 1). To suppress decomposition in the overnight reaction at room temperature, the reaction time was reduced to 1.5 h, which afforded [4.3.3]_CHO in an isolated yield of 80% (Table 1, entry 2). The

• electrophilic functionalization. a) Synthesis of methylene-alternating copolymers of fully π-fused propellanes. DCE, 1,2-dichloroethane. b) 1H NMR (500 MHz, top) and 13C (126 MHz, bottom) NMR spectra of [4.3.3]_CH2OH and [4.3.3]_linear in CDCl3 at room temperature. Gas adsorption (filled circles) and desorption

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

• in 89–98% yields. Reactions of 4 with acryloyl chloride (5, 1.5 equiv) in the presence of Et3N (2 equiv) at room temperature in anhydrous CH2Cl2 for 6 h afforded 19 N-acylated compounds 6 in 80–90% yields [19]. With N-acylated GBB adducts 6 in hand, the synthesis of imidazopyridine-fused

• irradiation at 100 °C for 1 h (Scheme 2, Table S1 in Supporting Information File 1). Nineteen distinct adducts 4 were obtained in 89–98% yields. The reactions of GBB adducts 4 with acryloyl chloride (5, 1.5 equiv) in the presence of Et3N (2 equiv) at room temperature in anhydrous CH2Cl2 for 6 h afforded 19 N

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

• presence of DCC and DMAP. The reaction was allowed to proceed for 6 h at room temperature, after which the temperature was reduced to −10 °C, and sodium borohydride was added. The mixture was left to react for 12 hours, yielding compound 53 in 96%. This intermediate was then converted to acrylic acid 54 by