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Search for "silica gel" in Full Text gives 1106 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Phenolic constituents from twigs of Aleurites fordii and their biological activities

  • Kyoung Jin Park,
  • Won Se Suh,
  • Da Hye Yoon,
  • Chung Sub Kim,
  • Sun Yeou Kim and
  • Kang Ro Lee

Beilstein J. Org. Chem. 2021, 17, 2329–2339, doi:10.3762/bjoc.17.151

Graphical Abstract
  • SYNAPT G2 mass spectrometer and semipreparative HPLC was conducted using a Gilson 306 pump with a Shodex refractive index detector and a Phenomenex Luna 10 μm column (250 × 10 mm). Silica gel 60 (Merck, Darmstadt, 70–230 mesh, and 230–400 mesh) and RP-C18 silica gel (Merck, 230–400 mesh) were used for
  • column chromatography. Low-pressure liquid chromatography was performed over Merck LiChroprep Lobar-A Si gel 60 (240 × 10 mm) with an FMI QSY-0 pump (ISCO). Merck precoated silica gel F254 plates and RP-18 F254s plates were used for TLC. Spots were detected on TLC under UV light or by heating after
  • –C6). Fraction C1 (2.0 g) was subjected to RP-C18 silica gel chromatography, eluting with gradient solvent system (30 → 100% aq. MeOH) to yield four subfractions (C2A–C2D). Fraction C2C (210 mg) was purified by semipreparative HPLC (2 mL/min, 50% aq. MeOH) to yield compounds 17 (5 mg) and 19 (6 mg
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Published 07 Sep 2021

Synthesis of O6-alkylated preQ1 derivatives

  • Laurin Flemmich,
  • Sarah Moreno and
  • Ronald Micura

Beilstein J. Org. Chem. 2021, 17, 2295–2301, doi:10.3762/bjoc.17.147

Graphical Abstract
  • chromatography (TLC) was performed on Marchery-Nagel Polygram SIL G/UV254 plates. Column chromatography was done on silica gel 60 (70–230 mesh). 1H, and 13C NMR spectra were recorded on Bruker DRX 300 MHz, Bruker Avance 4 Neo 400 MHz, and Bruker Avance 4 Neo 700 MHz instruments. Chemical shifts (δ) are reported
  • . Compound 3 [29][30][31] (200 mg, 0.720 mmol) was added and the mixture was heated to 110 °C in a pressure tube for 24 h. After neutralization with glacial acetic acid the volatiles were removed in vacuo. The crude product was dry-loaded onto silica gel and purified via flash column chromatography (5–20
  • combined organic layers were washed with brine and dried over magnesium sulfate. The solvents were removed and the remaining crude product was purified by flash column chromatography on silica gel (10–30% ethyl acetate in cyclohexane) to give 1.00 g of compound 4 (79%) as a white foam. TLC: 40% ethyl
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Published 02 Sep 2021

Transition-metal-free intramolecular Friedel–Crafts reaction by alkene activation: A method for the synthesis of some novel xanthene derivatives

  • Tülay Yıldız,
  • İrem Baştaş and
  • Hatice Başpınar Küçük

Beilstein J. Org. Chem. 2021, 17, 2203–2208, doi:10.3762/bjoc.17.142

Graphical Abstract
  • and were characterized by IR and GC–MS. All novel pruducts were characterized by IR, 1H NMR, 13C NMR, elemental analysis and GC–MS. The reactions were monitored by TLC using silica gel plates and the products were purified by flash column chromatography on silica gel (Merck; 230–400 mesh), eluting
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Published 30 Aug 2021

Nomimicins B–D, new tetronate-class polyketides from a marine-derived actinomycete of the genus Actinomadura

  • Zhiwei Zhang,
  • Tao Zhou,
  • Taehui Yang,
  • Keisuke Fukaya,
  • Enjuro Harunari,
  • Shun Saito,
  • Katsuhisa Yamada,
  • Chiaki Imada,
  • Daisuke Urabe and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2194–2202, doi:10.3762/bjoc.17.141

Graphical Abstract
  • medium, and the whole culture broth was extracted with 1-butanol. The extract was subjected to silica gel and ODS column chromatography, and the final purification was achieved by reversed-phase HPLC to yield two new spirotetronate polyketides, nomimicins B (1) and C (2), along with a known compound
  • from the aqueous layer containing the mycelium. Evaporation of the solvent gave 3.8 g of extract from 2 L of A16 culture. The extract was subjected to silica gel column chromatography with a step gradient of CHCl3/MeOH (1:0, 20:1, 10:1, 4:1, 2:1, 1:1, and 0:1, v/v). Fraction 4 (4:1) was concentrated to
  • silica gel column chromatography with a gradient of CHCl3/MeOH (1:0, 20:1, 10:1, 4:1, 2:1, 1:1, and 0:1, v/v). Fraction 7 (0:1) was concentrated to give 0.37 g of brown oil, which was then fractionated by ODS column chromatography with a gradient of MeCN + 0.1% HCO2H solution (2:8, 3:7, 4:6, 5:5, 6:4, 7
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Published 27 Aug 2021

Facile and innovative catalytic protocol for intramolecular Friedel–Crafts cyclization of Morita–Baylis–Hillman adducts: Synergistic combination of chiral (salen)chromium(III)/BF3·OEt2 catalysis

  • Karthikeyan Soundararajan,
  • Helen Ratna Monica Jeyarajan,
  • Raju Subimol Kamarajapurathu and
  • Karthik Krishna Kumar Ayyanoth

Beilstein J. Org. Chem. 2021, 17, 2186–2193, doi:10.3762/bjoc.17.140

Graphical Abstract
  • filtration, the solvent was removed under reduced pressure and the crude product was purified on silica gel (using hexane/EtOAc) to afford the desired product 6a as a white solid (81%). Methyl 1H-indene-2-carboxylate (6a): Yield: 160 mg (81%); white solid; mp 85–87 °C; IR (cm−1): 3062, 2953, 2884, 1947, 1735
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Published 26 Aug 2021

Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)

  • Tania Xavier,
  • Sylvie Condon,
  • Christophe Pichon,
  • Erwan Le Gall and
  • Marc Presset

Beilstein J. Org. Chem. 2021, 17, 2085–2094, doi:10.3762/bjoc.17.135

Graphical Abstract
  • . Another advantage inherent to this class of reagents is their easy purification by a classical acid/base work-up thanks to the presence of the carboxylic acid moiety, even if they could also be purified by standard chromatography on silica gel. They have thus been used in a variety of reactions, the most
  • DCC and 5 mol % of DMAP in CH2Cl2, Table 4, entry 1), the desired product was isolated in an encouraging yield of 22% after chromatography on silica gel. By adding a solution of DCC in CH2Cl2 to a solution of the other reagents in CH3CN (Table 4, entry 2), the yield was increased to 46%. The
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Published 18 Aug 2021

Recent advances in the syntheses of anthracene derivatives

  • Giovanni S. Baviera and
  • Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

Graphical Abstract
  • convenient synthesis of triarylmethanes and 9,10-diarylanthracenes from reactions of arenes and aromatic aldehydes by using acetyl bromide in the presence of silica gel-supported zinc bromide [43]. The methodology developed by these authors involved using excess of one of the reagents. When the authors
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Published 10 Aug 2021

2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

  • Najeh Tka,
  • Mohamed Adnene Hadj Ayed,
  • Mourad Ben Braiek,
  • Mahjoub Jabli,
  • Noureddine Chaaben,
  • Kamel Alimi,
  • Stefan Jopp and
  • Peter Langer

Beilstein J. Org. Chem. 2021, 17, 1629–1640, doi:10.3762/bjoc.17.115

Graphical Abstract
  • by thin-layer chromatography (TLC) using commercial silica-gel plate 60 coated with a fluorescence indicator and the visualization was performed by UV (254 nm). Organic compounds were purified using Merck Silica gel 60 (0.043–0.06 mm). Solvents for work-up and column chromatography were distilled
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Published 16 Jul 2021

Copper-mediated oxidative C−H/N−H activations with alkynes by removable hydrazides

  • Feng Xiong,
  • Bo Li,
  • Chenrui Yang,
  • Liang Zou,
  • Wenbo Ma,
  • Linghui Gu,
  • Ruhuai Mei and
  • Lutz Ackermann

Beilstein J. Org. Chem. 2021, 17, 1591–1599, doi:10.3762/bjoc.17.113

Graphical Abstract
  • determined by 1H NMR spectroscopy. Chromatographic separation was carried out on silica gel 60H (200–300 mesh) manufactured by Qingdao Haiyang Chemical Group Co. (China). High-resolution mass spectrometry (HRMS) was measured on a Thermo-DFS mass spectrometer. NMR spectra were recorded on a JEOL 600 NMR
  • ® pad, the reaction mixture was extracted with EtOAc (3 × 20 mL). The combined organic phase was washed with brine (20 mL) and dried over Na2SO4. Then, Et3N (0.5 mL) and silica gel (0.8 g) were added, and the combined solvent was removed under reduced pressure. The residue solid sample was purified by
  • column chromatography on silica gel (petroleum/EtOAc 5:1 to 2:1, with 1% Et3N), yielding the desired product 3. (Z)-3-Benzylidene-2-(methyl[pyridin-2-yl]amino)isoindolin-1-one (3aa) The general procedure was followed using hydrazide 1a (68.2 mg, 0.30 mmol) and alkyne 2a (91.9 mg, 0.90 mmol). Purification
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Published 08 Jul 2021

Breaking paracyclophane: the unexpected formation of non-symmetric disubstituted nitro[2.2]metaparacyclophanes

  • Suraj Patel,
  • Tyson N. Dais,
  • Paul G. Plieger and
  • Gareth J. Rowlands

Beilstein J. Org. Chem. 2021, 17, 1518–1526, doi:10.3762/bjoc.17.109

Graphical Abstract
  • chromatography was carried out on silica gel (grade 60, mesh size 230–400, Scharlau). Visualization techniques for TLC plates include using ultraviolet light (254 nm) and KMnO4. NMR spectra were collected at room temperature on Bruker-500, or Bruker-700 spectrometers and calibrated to the appropriate solvent
  • silica-gel chromatography (100% hexane), to furnish (±)-4 as a yellow solid (6.70 g, 26.5 mmol, 55%), (±)-5 as a yellow crystalline solid (1.68 g, 6.24 mmol, 13%), and 6 as light yellow crystals (2.61 g, 9.15 mmol, 19%). 4-Nitro[2.2]paracyclophane (4) 1H NMR (500 MHz, CDCl3) δ (ppm) 7.22 (d, J = 1.2 Hz
  • (5.00 g, 17.5 mmol, 1.00 equiv) in CH3OH (0.20 M, 87.6 mL) was added TFA (1.00 M, 17.5 mL) and stirred at rt for 24 h. The solution was concentrated under reduced pressure yielding a light orange solid, which was purified by flash silica-gel chromatography (gradient of 0% to 60% EtOAc, hexane over 1 h
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Published 29 Jun 2021

A straightforward conversion of 1,4-quinones into polycyclic pyrazoles via [3 + 2]-cycloaddition with fluorinated nitrile imines

  • Greta Utecht-Jarzyńska,
  • Karolina Nagła,
  • Grzegorz Mlostoń,
  • Heinz Heimgartner,
  • Marcin Palusiak and
  • Marcin Jasiński

Beilstein J. Org. Chem. 2021, 17, 1509–1517, doi:10.3762/bjoc.17.108

Graphical Abstract
  • conducted in air. Products were purified by standard column chromatography (CC) on silica gel (230–400 mesh; deactivated prior to use with 2% Et3N in petroleum ether) by using freshly distilled solvents as eluents (petroleum ether, CH2Cl2, AcOEt) or recrystallized from hot CHCl3. THF was dried over sodium
  • until the starting material 1 was fully consumed (based on TLC monitoring, petroleum ether/dichloromethane 1:1). After the resulting precipitate and unconsumed carbonate were filtered off, the solvent was removed under reduced pressure. The crude mixtures were purified by CC using silica gel as the
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Published 28 Jun 2021

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

  • Premansh Dudhe,
  • Mena Asha Krishnan,
  • Kratika Yadav,
  • Diptendu Roy,
  • Krishnan Venkatasubbaiah,
  • Biswarup Pathak and
  • Venkatesh Chelvam

Beilstein J. Org. Chem. 2021, 17, 1453–1463, doi:10.3762/bjoc.17.101

Graphical Abstract
  • thin-layer chromatography (TLC) was carried out on silica gel plates (silica gel 60 F254 aluminum supported plates), and the spots were visualized with a UV lamp (254 nm and 365 nm) or using chemical staining with Brady’s reagent, KMnO4, ninhydrin, iodine, and bromocresol. Column chromatography was
  • performed using silica gel (100–200 mesh or 230–400 mesh) and neutral alumina (175 mesh). DMF, DCM, DMA, toluene, and acetonitrile were dried using CaH2 and distilled over flame-dried 4 Å molecular sieves. THF and Et2O were dried over Na/benzophenone and stored over flame-dried 4 Å molecular sieves under an
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Published 17 Jun 2021

Organocatalytic asymmetric Michael/acyl transfer reaction between α-nitroketones and 4-arylidenepyrrolidine-2,3-diones

  • Chandrakanta Parida and
  • Subhas Chandra Pan

Beilstein J. Org. Chem. 2021, 17, 1447–1452, doi:10.3762/bjoc.17.100

Graphical Abstract
  • 2 (0.1 mmol), 10 mol % VII in 0.6 mL 1,2-dichloroethane were reacted at 25 °C for 12 hours. Yields correspond to isolated yields after silica gel column chromatography and ees were determined by chiral HPLC. Catalyst screening and optimization of the reaction conditions. Scope of α-nitroketones 2 in
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Published 14 Jun 2021
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  • . Pyrrole was used after distillation. Analytical thin-layer chromatography (TLC) was performed on aluminium plates coated with silica gel by using a suitable mixture of EtOAc and petroleum ether for development. Column chromatography was performed by using silica gel (100–200 mesh) with an appropriate
  • crude product was extracted with ethyl acetate. The combined organic layer was washed with water (100 mL × 2) and dried over Na2SO4. After evaporation of the solvents, the residue was passed through silica gel to give the final product as a white powder (7.5 g, 95%). The 1H NMR spectrum was perfectly
  • ) was degassed with nitrogen for 15 min. After adding the Grubbs’ catalyst (15 mol %), the stirring was continued for 12 h at the same temperature. Next, the solvent was removed under reduced pressure followed by silica gel column chromatography (5% EtOAc/petroleum ether) provided the required product 6
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Published 02 Jun 2021

Fritsch–Buttenberg–Wiechell rearrangement of magnesium alkylidene carbenoids leading to the formation of alkynes

  • Tsutomu Kimura,
  • Koto Sekiguchi,
  • Akane Ando and
  • Aki Imafuji

Beilstein J. Org. Chem. 2021, 17, 1352–1359, doi:10.3762/bjoc.17.94

Graphical Abstract
  • (Scheme 3a). The 2,2-unsymmetrically substituted sulfoxides 2d–g were obtained as mixtures of geometric isomers that were separated by column chromatography on silica gel. FBW rearrangement of magnesium alkylidene carbenoids Based on the results of DFT calculations, the degree of the vinylidene character
  • air- or water-sensitive compounds were conducted under an argon atmosphere. Argon gas was dried by passage through P2O5. Anhydrous THF and toluene were purchased and used as supplied. Silica gel 60N containing 0.5% fluorescence reagent 254 and a quartz column were used for column chromatography, and
  • water (50 mL), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/EtOAc 1:1) to give the alcohol [6.90 g, 16.7 mmol, 83%, Rf = 0.45 (hexane/EtOAc 1:1)] as a single diastereomer; yellow solid; mp 102.5–104.0 °C; IR (ATR
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Published 28 May 2021

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

  • Guido Gambacorta,
  • James S. Sharley and
  • Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Graphical Abstract
  • of 1,2-aminoalcohol 110 (90% yield, anti/syn 7:3, 78% ee). At the end of the Henry reaction an in-line plug of silica gel removes the catalyst before the second reduction step to prevent issues of chelation and palladium deactivation. Knoevenagel condensations are also of considerable interest to the
  • aminopropyl-functionalised silica gel (AP-T). The reagents (10 mmol) were eluted through the column in the same way as gravimetric chromatography is performed (Scheme 27). In this way, the authors claimed the product was completely collected after 250 mL of toluene elution. The silianol groups on the AP-T
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Published 18 May 2021

Structural effects of meso-halogenation on porphyrins

  • Keith J. Flanagan,
  • Maximilian Paradiz Dominguez,
  • Zoi Melissari,
  • Hans-Georg Eckhardt,
  • René M. Williams,
  • Dáire Gibbons,
  • Caroline Prior,
  • Gemma M. Locke,
  • Alina Meindl,
  • Aoife A. Ryan and
  • Mathias O. Senge

Beilstein J. Org. Chem. 2021, 17, 1149–1170, doi:10.3762/bjoc.17.88

Graphical Abstract
  • analytical grade and supplied by Sigma-Aldrich, Frontier Scientific, Inc., Tokyo Chemical Company and Acros chemicals and used without further purification unless otherwise stated. Flash column chromatography was carried out using Fluka Silica Gel 60 (230–400 mesh; Merck. Melting points are uncorrected and
  • pressure. The residue was filtered through silica gel using DCM. Column chromatography was performed through silica gel (hexane/DCM, 15:1–2:1, v/v). Further column chromatography was carried out on silica gel (hexane/DCM, 15:1–1:1, v/v) yielding the purple solid 4 (51 mg, 51%). To obtain single crystals
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Published 14 May 2021

Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide phenyl thioglycosides

  • Vojtěch Hamala,
  • Lucie Červenková Šťastná,
  • Martin Kurfiřt,
  • Petra Cuřínová,
  • Martin Dračínský and
  • Jindřich Karban

Beilstein J. Org. Chem. 2021, 17, 1086–1095, doi:10.3762/bjoc.17.85

Graphical Abstract
  • deoxyfluorination, which would likely occur with the β-anomers of 14–19 [41]. The complete separation of the α-anomer by conventional silica gel column chromatography was possible for thioglycosides 14, 16, 17, and 19, while the products 15 and 18 were obtainable as enriched α-anomers (α/β ≥ 3.3:1). Cleavage of the
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Published 11 May 2021

Synthetic accesses to biguanide compounds

  • Oleksandr Grytsai,
  • Cyril Ronco and
  • Rachid Benhida

Beilstein J. Org. Chem. 2021, 17, 1001–1040, doi:10.3762/bjoc.17.82

Graphical Abstract
  • 30 min. The products were separated by filtration and repeatedly washed in cold water. Finally, the derivatives were purified by column chromatography on silica gel to yield the compounds with moderate to good yields (40–81%). Previously some other examples have been described, and they all followed
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Published 05 May 2021

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

  • Christopher Liczner,
  • Kieran Duke,
  • Gabrielle Juneau,
  • Martin Egli and
  • Christopher J. Wilds

Beilstein J. Org. Chem. 2021, 17, 908–931, doi:10.3762/bjoc.17.76

Graphical Abstract
  • chloride, affording both 2'-OMe and 3'-OMe regioisomers. Fortunately, these isomers could be separated by silica gel column chromatography. Other synthetic approaches have since been developed [109][110][111], however, this pioneering work should be appreciated as nowadays, the 2'-OMe phosphoramidites of
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Published 28 Apr 2021

Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions

  • Dat Phuc Tran,
  • Yuki Sato,
  • Yuki Yamamoto,
  • Shin-ichi Kawaguchi,
  • Shintaro Kodama,
  • Akihiro Nomoto and
  • Akiya Ogawa

Beilstein J. Org. Chem. 2021, 17, 866–872, doi:10.3762/bjoc.17.72

Graphical Abstract
  • was complete, sulfur (3 equiv) was added under inert atmosphere and then the mixture was stirred at 60 °C for 6 h to provide the stable adduct 3. The purification of the products was performed by silica gel column chromatography using isohexane/MeOAc as an eluent. Radical addition of Ph2PPPh2 and Ph2P
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Published 20 Apr 2021

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

  • Shivani Gulati,
  • Stephy Elza John and
  • Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

Graphical Abstract
  • -assisted four-component reaction involving chromene-aldehyde (61), amines 32, acyclic 1,3-diketones 54 and nitromethane using silica-gel-supported polyphoshoric acid as catalyst under neat conditions for the synthesis of tetra-substituted pyrroles 62. A comparative study of the protocol employing the
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Published 19 Apr 2021

A chromatography-free and aqueous waste-free process for thioamide preparation with Lawesson’s reagent

  • Ke Wu,
  • Yichen Ling,
  • An Ding,
  • Liqun Jin,
  • Nan Sun,
  • Baoxiang Hu,
  • Zhenlu Shen and
  • Xinquan Hu

Beilstein J. Org. Chem. 2021, 17, 805–812, doi:10.3762/bjoc.17.69

Graphical Abstract
  • reference data. Melting points were determined on a Büchi M-565 apparatus. All reagents were obtained from commercial suppliers and used without further purification. The reactions were monitored by thin-layer chromatography. Column chromatography was performed using silica gel (300–400 mesh). Amides 1a–l
  • . The solvent was removed under reduced pressure. The reside was purified by silica gel column chromatography using petroleum ether/ethyl acetate as the eluent to afford the desired thioamide 2. Synthesis of N2,N6-di(n-butyl)pyridine-2,6-(carbothioamide) (3) [34] To a 500 mL four-necked flask were added
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Published 09 Apr 2021

Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane

  • David Weinzierl and
  • Mario Waser

Beilstein J. Org. Chem. 2021, 17, 800–804, doi:10.3762/bjoc.17.68

Graphical Abstract
  • recovered (Rp)-2 and ester (Sp)-3a with reasonable enantiomeric excesses around 90%, depending on the conversion. These two compounds can easily be separated by silica gel column chromatography in almost quantitative yields, thus providing a novel entry to obtain these interesting planar chiral motives in
  • alcohol 2 and ester 3a were separated by silica gel column chromatography (heptanes/ethyl acetate 10:1), yielding (Sp)-3a in 53% (175 mg) and (Rp)-2 in 43% (98 mg) (39%). (Rp)-2a: Analytical data match those reported in literature [18][19][20][26][28][39]. TLC (heptanes/ethyl acetate 10:1; Rf = 0.11). [α
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Published 08 Apr 2021

Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles

  • Soumyaranjan Pati,
  • Renata G. Almeida,
  • Eufrânio N. da Silva Júnior and
  • Irishi N. N. Namboothiri

Beilstein J. Org. Chem. 2021, 17, 762–770, doi:10.3762/bjoc.17.66

Graphical Abstract
  • excellent yields. Nucleophilic addition to 5- and 6-membered cyclic tosyloxyenones. Synthesis, functionalization and applications of triazoles. The reaction was performed using 0.2 mmol N-tosyl-1,2,3-triazole 1 and 0.2 mmol of cyclohexyl-1,3-dione 2. Yields are determined after silica gel column
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Published 31 Mar 2021
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