Synthesis and properties of 6-alkynyl-5-aryluracils

• Ruben Manuel Figueira de Abreu,
• Till Brockmann,
• Alexander Villinger,
• Peter Ehlers and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 898–911, doi:10.3762/bjoc.20.80

• was performed on Merck Silica gel 60 (particle size 63–200 μm). Solvents for extraction and column chromatography were distilled prior employment. Representative method for the preparation of starting materials 5-Bromo-6-chloro-1,3-dimethyluracil (2). Uracil 1 (22.9 mmol; 4.00 g) was dissolved in

Advancements in hydrochlorination of alkenes

• Daniel S. Müller

Beilstein J. Org. Chem. 2024, 20, 787–814, doi:10.3762/bjoc.20.72

• -workers [10][58]. They observed that silica gel and alumina, when thermally equilibrated (120 °C, 48 h), facilitated efficient hydrochlorinations when treated with HCl or reactive chlorides. A compelling demonstration of the potent role of silica gel is presented in Table 4. In the absence of silica gel

• , cycloheptene (61), when exposed to a concentrated solution of HCl in dichloromethane, did not show any reaction (Table 4, entry 1). Under the same conditions, in the presence of silica gel, they observed 97% conversion and a GC yield of 62% for chloride 62 (Table 4, entry 2). Further optimization identified

• and the surface area of the silica gel or alumina. Ethereal solvents were found to yield hydrochlorination reactions only with highly reactive alkenes, such as pinene. Subsequent studies revealed the need to adapt the hydrochlorination procedure for each substrate (e.g., Table 5). For instance, the

Isolation and structure determination of a new analog of polycavernosides from marine Okeania sp. cyanobacterium

• Kairi Umeda,
• Naoaki Kurisawa,
• Ghulam Jeelani,
• Tomoyoshi Nozaki,
• Kiyotake Suenaga and
• Arihiro Iwasaki

Beilstein J. Org. Chem. 2024, 20, 645–652, doi:10.3762/bjoc.20.57

• hexane. The aqueous MeOH portion was purified by reversed-phase column chromatography (ODS silica gel, MeOH/H2O), automated flash chromatography (hexane/EtOAc), and repeated reversed-phase HPLC to give polycavernoside E (1, 0.5 mg as a colorless oil). The isolation of compound 1 was directed by its

• based on HMBC and HMQC experiments. HRESIMS spectra were obtained on a Bruker timsTOF mass spectrometer. For reversed-phase column chromatography, ODS silica gel Cosmosil 75C18-OPN (Nacalai Tesque) was used. For medium pressure column chromatography, AFCS (Smart Flash AKROS, Yamazen) consisting of a

Chemical and biosynthetic potential of Penicillium shentong XL-F41

• Ran Zou,
• Xin Li,
• Xiaochen Chen,
• Yue-Wei Guo and
• Baofu Xu

Beilstein J. Org. Chem. 2024, 20, 597–606, doi:10.3762/bjoc.20.52

• extract was partitioned between EtOAc and H2O. The EtOAc fraction was chromatographed repeatedly over silica gel and reversed-phase high-performance liquid chromatography (RP-HPLC), resulting in the isolation of pure compounds 1–12 (Figure 2). According to literature reports of known compounds, some of

• IMS Q-Tof liquid chromatograph mass spectrometer. For NMR analysis, we utilized an AVANCE II 600 spectrometer, referencing residual solvent peaks at δH/δC 7.27/77.0 ppm in CDCl3 for chemical shift calibration. We utilized commercial silica gel from Yantai Xinnuo New Material Technology Co., Ltd

• gradient of petroleum ether–ethyl acetate (PE–EA) and ethyl acetate–methanol (EA–MeOH) to yield 22 fractions (Fr.A–Fr.N) as determined by TLC analysis. Fraction Fr.J (62.32 mg) was further purified using silica gel column chromatography with a PE–EtOAc gradient to obtain nine subfractions (Fr.J1–Fr.J9

A myo-inositol dehydrogenase involved in aminocyclitol biosynthesis of hygromycin A

• Michael O. Akintubosun and
• Melanie A. Higgins

Beilstein J. Org. Chem. 2024, 20, 589–596, doi:10.3762/bjoc.20.51

• . Reactions for thin-layer chromatography analysis were carried out using the same general reaction conditions reported above. Six μL of each reaction were spotted on the TLC silica gel 60 F254 (Sigma) and run with a solvent system containing butanol/ethanol/water 5:4:3. The TLC was stained using a solution

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

• Jens Frackenpohl,
• David M. Barber,
• Guido Bojack,
• Birgit Bollenbach-Wahl,
• Ralf Braun,
• Rahel Getachew,
• Sabine Hohmann,
• Kwang-Yoon Ko,
• Karoline Kurowski,
• Bernd Laber,
• Rebecca L. Mattison,
• Thomas Müller,
• Anna M. Reingruber,
• Dirk Schmutzler and
• Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

• -ynylcarbamoyl)-1,3-dioxolane-2-carboxamide [3] and FAM azide, 5-isomer (Broadpharm BP-22544, San Diego, CA) by click chemistry [29] and was purified by flash column chromatography on silica gel. Preemergence efficacy of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridine-based FAT inhibitors 7b, 7c, and 13b as well as

A new analog of dihydroxybenzoic acid from Saccharopolyspora sp. KR21-0001

• Rattiya Janthanom,
• Yuta Kikuchi,
• Hiroki Kanto,
• Tomoyasu Hirose,
• Arisu Tahara,
• Takahiro Ishii,
• Arinthip Thamchaipenet and
• Yuki Inahashi

Beilstein J. Org. Chem. 2024, 20, 497–503, doi:10.3762/bjoc.20.44

• flowthrough fraction was adjusted to 3 with formic acid (FA) and chromatographed again on HP20 column. Now, 1 was retained in the resin and eluted by 50% MeOH with 0.05% FA. Then 1 was purified by silica gel and ODS column chromatography, and ethyl acetate extraction under acidic conditions. As the result of

• and extracted with ethyl acetate. The ethyl acetate layer was purified using a silica gel column (25 i.d. × 300 mm) by eluting with CHCl3/MeOH (100:0, 100:1, 100:2, 10:1, 1:1, and 0:100). The 10:1 fraction was purified with an ODS column (47 i.d. × 260 mm) by eluting with MeOH/H2O (0%, 10%, 20%, 30

Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus Pseudallescheria boydii CS-793

• Zhen Ying,
• Xiao-Ming Li,
• Sui-Qun Yang,
• Hong-Lei Li,
• Xin Li,
• Bin-Gui Wang and
• Ling-Hong Meng

Beilstein J. Org. Chem. 2024, 20, 470–478, doi:10.3762/bjoc.20.42

• Discussion For chemical investigation, the solvent EtOAc was used to extract the fermentation culture of the fungus P. boydii CS-793 to afford an organic extract. Isolation and purification of the crude extract with a combination of column chromatography (CC) by Lobar LiChroprep RP-18, silica gel, Sephadex

• by Chromeleon software (version 6.80). LC–MS were obtained with a Bruker maXis plus Q-TOF. Column chromatography was carried out using commercially available silica gel (200–300 mesh, Qingdao Haiyang Chemical Co.), Lobar LiChroprep RP-18 (40–63 μm, Merck), and Sephadex LH-20 (Pharmacia). Thin-layer

• CC on silica gel eluting with a CH2Cl2/MeOH gradient (from 200:1 to 100:1) and then by preparative TLC (plate: 20 × 20 cm, developing solvents: ether/acetone 2:1) to afford compound 4 (8.6 mg). Fr. 5.4 (538 mg) was separated by CC on Si gel and Sephadex LH-20 (MeOH), after that compounds 1 (12.5 mg

Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas

• Alexander S. Hampton,
• David R. W. Hodgson,
• Graham McDougald,
• Linhua Wang and
• Graham Sandford

Beilstein J. Org. Chem. 2024, 20, 460–469, doi:10.3762/bjoc.20.41

• difluorinated product 5a in 85% isolated yield. Purification of 5a was achieved very readily by eluting the reaction mixture through a small quantity of silica gel with chloroform and evaporating the residual solvent to leave the crude product which could be further purified by recrystallization. Subsequently

• , a range of ethyl benzoylacetate derivatives was prepared (see Supporting Information File 1) [45][46] and successfully subjected to difluorination conditions (Table 3). Purification by column chromatography using the minimum amount of silica gel with chloroform as the eluent yielded 5c–g in high

Mono or double Pd-catalyzed C–H bond functionalization for the annulative π-extension of 1,8-dibromonaphthalene: a one pot access to fluoranthene derivatives

• Nahed Ketata,
• Linhao Liu,
• Ridha Ben Salem and
• Henri Doucet

Beilstein J. Org. Chem. 2024, 20, 427–435, doi:10.3762/bjoc.20.37

• of PdCl(C3H5)(dppb) (30.5 mg, 0.05 mmol) at 150 °C during 16 h in DMA (4 mL) under argon affords the coupling products 1–18 after evaporation of the solvent and purification on silica gel. Eluent EtOAc/heptane 1:9 for compounds 3–8, 10–18; heptane for compounds 1, 2, and 9. General procedure for the

• DMA (4 mL) under argon affords the coupling products 19–27 after evaporation of the solvent and purification on silica gel. Eluent EtOAc/heptane 1:9 for compounds 19–24; heptane for compounds 25 and 26; EtOAc/heptane 2:8 for compound 27. General procedure for the palladium-catalyzed synthesis of 9

• (4 mL) under argon affords the coupling products 28–30 after evaporation of the solvent and purification on silica gel. Eluent EtOAc/heptane 1:9 for all compounds. Structure of fluoranthene. Pd-catalyzed access to fluoranthenes. Scope of the Pd-catalyzed direct arylation reaction of arenes with 1,8

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

• acids, such as N-bromosuccinimide (NBS) [54], silica chloride [55], Ph3CCl [56], ZnO [57], La(NO3)3·6H2O [58], V(HSO4)3 [59], Cu(ClO4)2·6H2O [60], Fe/Al pillared clay [61], trimethylsilyl chloride (TMSCl) [62], BiCl3-loaded montmorillonite K10 [63][64][65][66][67], ZrO2-MgO [68] or CaO [69]. Silica gel

Additive-controlled chemoselective inter-/intramolecular hydroamination via electrochemical PCET process

• Kazuhiro Okamoto,
• Naoki Shida and
• Mahito Atobe

Beilstein J. Org. Chem. 2024, 20, 264–271, doi:10.3762/bjoc.20.27

• of 5 mA (3 F/mol, 57.9 C) through the CF anode (1 × 1 cm) and the Pt cathode (1 × 1 cm). The reaction mixture was concentrated in vacuo and Et2O (20 mL) was added. The resulting precipitate was removed by filtration through a short silica gel pad under reduced pressure. The filtrate was concentrated

• was removed by filtration through a short silica gel pad under reduced pressure. The filtrate was concentrated in vacuo and the resulting residue was subjected to 1H NMR spectroscopy or column chromatography. Application of amidyl radical species generated by PCET. (A) Effect of phosphate base on the

Chiral phosphoric acid-catalyzed transfer hydrogenation of 3,3-difluoro-3H-indoles

• Yumei Wang,
• Guangzhu Wang,
• Yanping Zhu and
• Kaiwu Dong

Beilstein J. Org. Chem. 2024, 20, 205–211, doi:10.3762/bjoc.20.20

• and the reaction mixture was stirred at room temperature for 3 h. After concentrating the mixture, the residue was purified by column chromatography on silica gel using a mixture of petroleum ether/ethyl acetate 30:1 (v/v) as the eluent to afford products 2. The yields were determined by 19F NMR

Comparison of glycosyl donors: a supramer approach

• Anna V. Orlova,
• Nelly N. Malysheva,
• Maria V. Panova,
• Nikita M. Podvalnyy,
• Michael G. Medvedev and
• Leonid O. Kononov

Beilstein J. Org. Chem. 2024, 20, 181–192, doi:10.3762/bjoc.20.18

• the stereoselectivity of sialylation, it is important to analyze anomeric ratio values (α/β) for the disaccharide fraction separated by size-exclusion chromatography since the retention values of different disaccharide anomers on silica gel may be surprisingly large and a minor isomer may be lost

• during purification by silica gel chromatography. On the other hand, NMR analysis of the crude reaction mixtures may be misleading due to possible overlap of the signals of H-3eq belonging both to disaccharide and monosaccharide derivatives sometimes present in such glycosylation mixtures. At low

• glycosylation reactions was distilled under argon over P2O5 and then over CaH2 and stored over molecular sieves (MS) 3 Å. Powdered MS 3 Å (Fluka) were activated before the reactions by heating at ≈220 °C in high vacuum for 6 h. Column chromatography was performed on silica gel 60 (40–63 μm, Merck). Gel

Synthesis of the 3’-O-sulfated TF antigen with a TEG-N₃ linker for glycodendrimersomes preparation to study lectin binding

• Mark Reihill,
• Hanyue Ma,
• Dennis Bengtsson and
• Stefan Oscarson

Beilstein J. Org. Chem. 2024, 20, 173–180, doi:10.3762/bjoc.20.17

• silica gel 60 F254. Visualisation was performed with UV-light (254 nm) fluorescence quenching, and/or by staining with an 8% H2SO4 dip (stock solution: 8 mL conc. H2SO4, 92 mL EtOH), ninhydrin dip (stock solution: 0.3 g ninhydrin, 3 mL AcOH, 100 mL EtOH) and/or ceric ammonium molybdate dip (stock

• solution: 25 g ammonium molybdate tetrahydrate, 0.5 g Ce(SO4)2, 50 mL H2SO4, 450 mL EtOH). Chromatography Silica gel flash chromatography was carried out using Davisil® LC60A (40–63 μm) silica gel or with automated flash chromatography systems, Buchi Reveleris® X2 (UV 200–500 nm and ELSD detection

• Celite® and concentrated in vacuo. The resulting residue was taken up in EtOAc (700 mL) and washed with 10% aq Na2S2O3 (700 mL), water (700 mL) and brine (700 mL). The organic phase was then dried over MgSO4, filtered and reduced to dryness. Flash chromatography on silica gel (toluene→toluene/EtOAc, 3:2

Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

• Michio Yamada

Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13

• ) affords 7 with 16% yield, 8 with 25% yield, and 9 with 46% yield. Furthermore, 7 and 8 are efficiently converted into 10 and 11, respectively, with high yields (80% and 95%, respectively) via column chromatography employing silica gel in acetonitrile, thereby instigating further molecular transformation

• surfactant, Brij 30, was used as the reaction solvent at a concentration of 20 mM, exceeding the critical micelle concentration, 4 and 37 were obtained in a ratio of 53:47, with 64% yield. Notably, 37 exhibits instability in silica gel and polar solvents. In particular, when 37 is kept in ethyl acetate or

Multi-redox indenofluorene chromophores incorporating dithiafulvene donor and ene/enediyne acceptor units

• Christina Schøttler,
• Kasper Lund-Rasmussen,
• Line Broløs,
• Philip Vinterberg,
• Ema Bazikova,
• Viktor B. R. Pedersen and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2024, 20, 59–73, doi:10.3762/bjoc.20.8

• molecular sieves, or by drying over 3 Å molecular sieves. All remaining anhydrous solvents were obtained from a solvent drying tower (IT model PS-MD-05). HPLC grade solvents were used unless otherwise specified. Purification by chromatography was performed using silica gel (flash: 40–63 μm, Sepacore® Flash

• Systems X10/X50: 40–63 μm). TLC was performed using aluminum sheets covered with silica gel coated with fluorescent indicator. NMR spectra were recorded on a Bruker instrument at 500 MHz and 126 MHz for 1H and 13C NMR, respectively. Deuterated chloroform (CDCl3, 1H = 7.26 ppm, 13C = 77.16 ppm), deuterated

Identification of the p-coumaric acid biosynthetic gene cluster in Kutzneria albida: insights into the diazotization-dependent deamination pathway

• Seiji Kawai,
• Akito Yamada,
• Yohei Katsuyama and
• Yasuo Ohnishi

Beilstein J. Org. Chem. 2024, 20, 1–11, doi:10.3762/bjoc.20.1

• (15 mg/L) was added to the culture, and the culture was continued for another 1 day. The pH was adjusted to 4 by adding 6 M HCl to the culture, and the metabolites were extracted by ethyl acetate. After the ethyl acetate was evaporated, the metabolites were absorbed for 5.0 g silica gel 60 (0.040

• –0.063 mm, Merck Millipore, Burlington, MA, USA). The silica gel holding the metabolites was applied to a normal-phase medium-pressure liquid chromatography system (MPLC, Shoko Scientific, Kanagawa, Japan) equipped with a silica column (Purif-Pack, Shoko Scientific), and the metabolites were eluted with

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

• Karolis Leitonas,
• Brigita Vigante,
• Dmytro Volyniuk,
• Audrius Bucinskas,
• Pavels Dimitrijevs,
• Sindija Lapcinska,
• Pavel Arsenyan and
• Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

• purification. Thin-layer chromatography (TLC) was performed using Merck Silica gel 60 F254 plates and visualized by UV (254 nm) fluorescence. Zeochem silica gel (ZEOprep 60/35–70 microns – SI23501) was used for column chromatography. 1H and 13C NMR spectra were recorded on a Bruker 400 spectrometer at 400 and

• for 1 h. After cooling, the reaction was quenched by the addition of ice and the precipitate was filtered off. The crude product was purified by flash chromatography on silica gel using chloroform as eluent yielding compound 3 (1.0 g, 78%) as white powder. Mp > 200 °C; 1H NMR (400 MHz, DMSO-d6) 7.91

• dried over Na2SO4. After the solvent was removed, the crude yellow product was carefully washed twice with acetonitrile to remove the starting materials. Further purification was achieved using flash chromatography on silica gel (eluent: dichloromethane/petroleum ether 1:2). Compound 4 (0.86 g, 61%) was

Substituent-controlled construction of A₄B₂-hexaphyrins and A₃B-porphyrins: a mechanistic evaluation

• Seda Cinar,
• Dilek Isik Tasgin and
• Canan Unaleroglu

Beilstein J. Org. Chem. 2023, 19, 1832–1840, doi:10.3762/bjoc.19.135

• , Kieselgel 60, F254, Merck) with visualization under UV light. Products were purified by silica gel flash column chromatography (0.05–0.63 mm, 230–400 mesh ASTM, E.Merck). N-Tosylimines 2a–m and 5,10-bis(pentafluorophenyl)tripyrromethane (1) were synthesized according to the previously reported literature

• )tripyrromethane (1, 0.090 mmol) in CH2Cl2 (1.5 mL) and the mixture was stirred at rt for 4 h. Afterwards, DDQ (0.180 mmol) was added to this solution and stirred for another 2 h. The resulting solution was eluted through a short silica gel column with EtOAc and the solvent was removed under reduced pressure. The

• residue was purified by silica gel column chromatography (EtOAc/hexane 1:50) or preparative thin-layer chromatography on silica gel (Silica gel 60, F254, Merck) where applicable to obtain A3B-porphyrins and A4B2-hexaphyrins. Yields of porphyrins 3a–k were between 9–22% and the yields of hexaphyrins 4b–g,j

A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen

• Gyula Dargó,
• Dóra Erdélyi,
• Balázs Molnár,
• Péter Kisszékelyi,
• Zsófia Garádi and
• József Kupai

Beilstein J. Org. Chem. 2023, 19, 1811–1824, doi:10.3762/bjoc.19.133

• achieved, for example, by immobilizing the catalysts to a solid support [15], e.g., silica gel [16][17][18], organic polymers [19][20][21], magnetic nanoparticles [22][23], or by membrane separation, e.g., using organic solvent nanofiltration (OSN) [24][25][26], which methods can be easily implemented in

• menthol. The reactions under pressure were carried out in a 150 mL pressure flask (Synthware Glass). Thin-layer chromatography (TLC) was performed using silica gel 60 F254 (Merck) plates. The spots of the materials on TLC plates were visualized by UV light at 254 nm. The reactions were monitored by TLC

Active-metal template clipping synthesis of novel [2]rotaxanes

• Cătălin C. Anghel,
• Teodor A. Cucuiet,
• Niculina D. Hădade and
• Ion Grosu

Beilstein J. Org. Chem. 2023, 19, 1776–1784, doi:10.3762/bjoc.19.130

• experimental data Commercially available reagents were used without further purification. Compounds 1 [43][47], 4 [48], 9 [49], 10 [44] and M2 [44] were synthesized according to procedures reported in the literature. Thin-layer chromatography (TLC) was performed on silica gel 60 coated aluminium F254 plates

• and visualized by UV irradiation at 254 nm. Preparative column chromatography was carried out using silica gel 60 (0.040–0.063 mm) from Merck. The NMR spectra were recorded on Bruker Avance 400 MHz or Bruker Avance 600 MHz spectrometers. Chemical shifts (δ) are reported in parts per million (ppm

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices

• Suangsiri Arunlimsawat,
• Patteera Funchien,
• Pongsakorn Chasing,
• Atthapon Saenubol,
• Taweesak Sudyoadsuk and
• Vinich Promarak

Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122

• chromatography over silica gel eluting with CH2Cl2/hexane 1:4 to give white solids (2.11 g, 87%). 1H NMR (600 MHz, CDCl3) δ 8.12 (d, J = 7.7 Hz, 2H), 7.40 (t, J = 7.8 Hz, 2H), 7.34 (d, J = 8.2 Hz, 2H), 7.28 (t, J = 8.0 Hz, 4H), 7.24 (d, J = 8.1 Hz, 2H), 7.21–7.07 (m, 15H); 13C NMR (151 MHz, CDCl3) δ 143.55

• was washed with water, brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was then purified by column chromatography over silica gel eluting with CH2Cl2/hexane 3:7 to give compound 3 as white solid (928 mg, 41% over two steps). 1H NMR (600 MHz

• purified by column chromatography over silica gel eluting with CH2Cl2/hexane 3:7, followed by recrystallization from a CH2Cl2/methanol mixture to obtain TPECNz as red solid (396.0 mg, 58%). Mp > 360 °C; 1H NMR (600 MHz, CDCl3) δ 8.43 (s, 2H), 8.15 (td, J = 7.1, 3.5 Hz, 4H), 7.74 (dd, J = 8.3, 1.7 Hz, 2H

Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect

• Ken-ichi Nakashima,
• Naohito Abe,
• Masayoshi Oyama,
• Hiroko Murata and
• Makoto Inoue

Beilstein J. Org. Chem. 2023, 19, 1604–1614, doi:10.3762/bjoc.19.117

• using an Agilent 6230 LC/TOF mass spectrometer. HPLC was performed on a Hitachi HPLC system equipped with an L-2130 pump, an L-2200 autosampler, an L-2300 column oven, and an L-2455 diode array detector. Silica gel AP-300 (Toyota Kako), Sephadex LH-20 (GE Healthcare), and Cosmosil 75C18-OPN (Nacalai

• Tesque) were used for column chromatography (CC). Silica gel 60 F254 and RP-18 F254S (Merck) were used for TLC analysis. Plant material B. disticha was cultivated in the greenhouse of Setsunan University medicinal plant garden (Osaka, Japan) in September 2014. Taxonomic identification was performed by an

• were concentrated in vacuo to yield the ethyl acetate fraction (11.8 g) and n-butanol fraction (7.4 g), respectively. The ethyl acetate fraction was separated by silica gel CC with CHCl3/MeOH (stepwise gradient of 100:1, 50:1, 30:1, 20:1, 15:1, 10:1, 8:1, and 0:1, v/v) as the eluent. The fractions were

Lewis acid-promoted direct synthesis of isoxazole derivatives

• Dengxu Qiu,
• Chenhui Jiang,
• Pan Gao and
• Yu Yuan

Beilstein J. Org. Chem. 2023, 19, 1562–1567, doi:10.3762/bjoc.19.113

• TLC monitoring. Upon completion, the solution was cooled to room temperature and the solvent was removed under vacuum directly. The crude residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether 40:1) to afford product 3a with 87% yield. Natural products and drug