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Search for "acetone" in Full Text gives 684 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

  • Soleiman E. Helaly,
  • Wilawan Kuephadungphan,
  • Patima Phainuphong,
  • Mahmoud A. A. Ibrahim,
  • Kanoksri Tasanathai,
  • Suchada Mongkolsamrit,
  • Janet Jennifer Luangsa-ard,
  • Souwalak Phongpaichit,
  • Vatcharin Rukachaisirikul and
  • Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2968–2981, doi:10.3762/bjoc.15.293

Graphical Abstract
  • the cultures were then harvested. The fermented broths were separated from the mycelia by vacuum filtration, and were both subsequently extracted according to the procedure described by Phainuphong and co-workers [49]. The fungal mycelia were extracted with acetone, followed by EtOAc instead of MeOH
  • from both strains were extracted with 4 L of EtOAc, giving dark brown oily residues, while their mycelia were extracted sequentially with acetone, followed by EtOAc to afford mycelial extracts as brown gum. They were all chemically profiled by HPLC–DAD–MS in order to optimize the chromatographic
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Published 16 Dec 2019

Synthesis and optoelectronic properties of benzoquinone-based donor–acceptor compounds

  • Daniel R. Sutherland,
  • Nidhi Sharma,
  • Georgina M. Rosair,
  • Ifor D. W. Samuel,
  • Ai-Lan Lee and
  • Eli Zysman-Colman

Beilstein J. Org. Chem. 2019, 15, 2914–2921, doi:10.3762/bjoc.15.285

Graphical Abstract
  • temperature, it is also carried out in benign acetone as solvent and does not require any additional oxidant. It circumvents the additional prefunctionalization of the BQ step usually required for Pd cross-couplings [15], while also showing greater functional group tolerance than radical-based methods [16][17
  • mg, 0.027 mmol, 15 mol %). Acetone (2.2 mL) was added and the reaction mixture was stirred for 18 h at rt. The crude mixture was directly adsorbed onto a silica gel column and purified using toluene as the eluent. Further purification using glass-backed silica plates with toluene as the eluent
  • (29.9 mg, 0.09 mmol, 15 mol %). Acetone (7.2 mL) was added and the reaction mixture stirred for 48 h at 30 °C. The crude mixture was adsorbed directly onto a silica gel column and subsequent purification with DCM/petroleum ether/toluene, 1:1:0.1 to 2:1:0.1, v/v as the eluent yielded the title product 3
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Published 04 Dec 2019

Skeletocutins M–Q: biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa

  • Tian Cheng,
  • Clara Chepkirui,
  • Cony Decock,
  • Josphat C. Matasyoh and
  • Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2782–2789, doi:10.3762/bjoc.15.270

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  • isolation as well as biological and physicochemical characterization. Results and Discussion The fruiting bodies of the fungal specimen MUCL56074 were extracted with acetone and subsequently purified via preparative HPLC, which led to the isolation of five previously undescribed secondary metabolites, 1–5
  • quantity of 9.8 g fruiting bodies were extracted using 500 mL of acetone overnight. Then, the extract was filtered and another 500 mL of acetone were added. This was extracted in an ultrasonic bath for 30 min. The extracts were combined and the solvent evaporated to afford 226 mg of crude extract
  • control, respectively. HPLC–UV chromatogram of the extract from fruiting bodies of Skeletocutis sp. (detection wavelength λ = 190–600 nm). Chemical structures of compounds 1–6. Inhibition Leu-AMC hydrolysis. a) c (ʟ-Leu-AMC) = 100 µM. b) c (ʟ-Leu-AMC) = 50 µM. 1H and 13C NMR data for 1 (in acetone-d6) and
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Published 19 Nov 2019

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

  • Munmun Ghosh,
  • Valmik S. Shinde and
  • Magnus Rueping

Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

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  • . Chiral solvents The only report on asymmetric electrochemical reaction in chiral solvent was published by Seebach and Oei in 1975 [53]. The asymmetric photodimerization of acetone to pinacol was conducted using amino-ether DDB 54 as a chiral solvent. Under the optimized reaction conditions, this
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Published 13 Nov 2019

Emission solvatochromic, solid-state and aggregation-induced emissive α-pyrones and emission-tuneable 1H-pyridines by Michael addition–cyclocondensation sequences

  • Natascha Breuer,
  • Irina Gruber,
  • Christoph Janiak and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 2684–2703, doi:10.3762/bjoc.15.262

Graphical Abstract
  • , and 6g recorded in dichloromethane at T = 298 K. Absorption (top) and fluorescence (bottom) of compound 6c with variable solvent polarity (left to the right: toluene, ethyl acetate, acetone, DMF and DMSO, c(6c) = 10−4 M; λexc = 365 nm, handheld UV lamp). Absorption (solid lines) and emission (dashed
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Published 12 Nov 2019

Acid-catalyzed rearrangements in arenes: interconversions in the quaterphenyl series

  • Sarah L. Skraba-Joiner,
  • Carter J. Holt and
  • Richard P. Johnson

Beilstein J. Org. Chem. 2019, 15, 2655–2663, doi:10.3762/bjoc.15.258

Graphical Abstract
  • °C via a dry ice/acetone bath. TiCl4 (0.14 g, 0.65 mmol) was added dropwise via syringe and the reaction mixture was warmed to 0 °C via an ice/water bath and stirred for 1 h. The product was extracted with ethyl acetate (3x) and dried with Na2SO4. The crude product was purified by chromatography with
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Published 06 Nov 2019

Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

  • Heather J. Lacey,
  • Cameron L. M. Gilchrist,
  • Andrew Crombie,
  • John A. Kalaitzis,
  • Daniel Vuong,
  • Peter J. Rutledge,
  • Peter Turner,
  • John I. Pitt,
  • Ernest Lacey,
  • Yit-Heng Chooi and
  • Andrew M. Piggott

Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256

Graphical Abstract
  • coverage of the grains. Extraction of the grains with acetone, followed by partitioning of the aqueous residue with EtOAc and defatting with hexane, provided an enriched extract of non-polar secondary metabolites. Fractionation by reversed-phase preparative HPLC (Figures S1 and S2 in Supporting Information
  • individual flasks, and extracted with acetone (2 × 3 L). The combined extracts were evaporated under vacuum to produce an aqueous slurry (500 mL). The slurry was partitioned against ethyl acetate (2 × 2 L) and the ethyl acetate was reduced in vacuo to an oily residue. The residue was dissolved in methanol
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Published 05 Nov 2019

Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence

  • Vânia F. Pais,
  • Tristan Neumann,
  • Ignacio Vayá,
  • M. Consuelo Jiménez,
  • Abel Ros and
  • Uwe Pischel

Beilstein J. Org. Chem. 2019, 15, 2612–2622, doi:10.3762/bjoc.15.254

Graphical Abstract
  • receptors for fluoride anions. Experimental General methods and materials 1H NMR spectra were recorded at 400 MHz or 500 MHz and 13C NMR spectra were recorded at 100 MHz or 125 MHz. Chloroform-d (CDCl3), acetone-d6 ((CD3)2CO) and benzene-d6 (C6D6) were used as solvents and the solvent peak was employed as
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Published 04 Nov 2019

Synthetic terpenoids in the world of fragrances: Iso E Super® is the showcase

  • Alexey Stepanyuk and
  • Andreas Kirschning

Beilstein J. Org. Chem. 2019, 15, 2590–2602, doi:10.3762/bjoc.15.252

Graphical Abstract
  • assigned as C13H20O [10]. In an attempt to recreate this compound by condensation of acetone with citral (28) a compound with “a strange but not very characteristic odour” was formed, later named pseudoionone (29, Scheme 1). It turned out not to be suited for further investigations. However, after cleaning
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Published 31 Oct 2019

Safe and highly efficient adaptation of potentially explosive azide chemistry involved in the synthesis of Tamiflu using continuous-flow technology

  • Cloudius R. Sagandira and
  • Paul Watts

Beilstein J. Org. Chem. 2019, 15, 2577–2589, doi:10.3762/bjoc.15.251

Graphical Abstract
  • suitable azidating agent undergoes a highly regio- and stereoselective nucleophilic substitution of allylic O-mesylate at the C-3 position affording azide compound 5 (Scheme 3). Nie and co-workers [19] reported the treatment of mesyl shikimate 4 with NaN3 (4 equiv) in aqueous acetone (Me2CO/H2O 5:1) at 0
  • (Chemtrix) was used to optimise the synthesis of azide compound 5 from mesyl shikimate 4 using aqueous NaN3 (Figure 2). Initial studies had shown the same conversions in both acetone and acetonitrile as solvents. Although acetone is a greener solvent than acetonitrile [21][22], its use was accompanied with
  • eventual microreactor blockage caused by a resulting precipitate from the acetone/aqueous NaN3 mixture. Fortunately, acetonitrile is also an acceptable green solvent [21][22]. Furthermore, acetonitrile has a higher boiling point than acetone which is desirable for high temperature reaction interrogation
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Published 30 Oct 2019

Probing of local polarity in poly(methyl methacrylate) with the charge transfer transition in Nile red

  • Aydan Yadigarli,
  • Qimeng Song,
  • Sergey I. Druzhinin and
  • Holger Schönherr

Beilstein J. Org. Chem. 2019, 15, 2552–2562, doi:10.3762/bjoc.15.248

Graphical Abstract
  • the solvent polarity properties are listed in Table 1. The data points for the dipolar aprotic solvents acetonitrile, acetone and ethyl acetate and the nonpolar n-hexane, shown by filled circles in Figure 3a, lie along a straight line. From its slope of −7210 cm−1 and μg = 11.97 D the value of μe
  • = 18.30 D is calculated. The fluorescence spectra of NR in the protic solvents ethanol and methanol are substantially shifted to the red (Figure 2a), although they possess similar f(ε) − f(n2) values compared to those for acetone and acetonitrile, respectively (Table 1). This effect is reminiscent of the
  • , namely the points for dipolar acetonitrile, acetone, ethyl acetate and nonpolar n-hexane fit to a straight line (2), NR in other solvents exhibits again a stronger red shift due to specific and inductive solute–solvent interactions. In order to eliminate any scaling effect of the Onsager radius on the
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Published 25 Oct 2019

Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene

  • Anna Kmieciak and
  • Marek P. Krzemiński

Beilstein J. Org. Chem. 2019, 15, 2493–2499, doi:10.3762/bjoc.15.242

Graphical Abstract
  • gas evolution ceased. Solvents were removed using a rotary evaporator and the resulting intermediate was dissolved in dichloromethane (6 mL). meta-Chloroperbenzoic acid (75%, 2.301 g, 10 mmol) was dissolved in dichloromethane (10 mL), cooled in a dry ice–acetone bath, and the intermediate solution was
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Published 22 Oct 2019

Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers

  • Anniina Kiesilä,
  • Jani O. Moilanen,
  • Anneli Kruve,
  • Christoph A. Schalley,
  • Perdita Barran and
  • Elina Kalenius

Beilstein J. Org. Chem. 2019, 15, 2486–2492, doi:10.3762/bjoc.15.241

Graphical Abstract
  • an Ionspec QFT-7 ESI-FT-ICR with a 7 T superconducting magnet. Samples for all mass spectrometric experiments were prepared with 10 or 20 µM concentration and 1:3 host–guest ratio in acetone. Theoretical CCS values were calculated using IMoS [20][21]. NMR experiments were performed with a Bruker
  • found in Supporting Information File 1. Spectra of 1 + Me4NPF6 1:3 in acetone in a) (+)ESI-MS and b) (−)ESI-MS. Insets showing arrival time distributions for selected ions. Identical drift times demonstrate the same structural diameters and CCS values for these ions. Separate arrival time distributions
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Published 21 Oct 2019

Experimental and computational electrochemistry of quinazolinespirohexadienone molecular switches – differential electrochromic vs photochromic behavior

  • Eric W. Webb,
  • Jonathan P. Moerdyk,
  • Kyndra B. Sluiter,
  • Benjamin J. Pollock,
  • Amy L. Speelman,
  • Eugene J. Lynch,
  • William F. Polik and
  • Jason G. Gillmore

Beilstein J. Org. Chem. 2019, 15, 2473–2485, doi:10.3762/bjoc.15.240

Graphical Abstract
  • nitrogen-purged MBraun MBS-SPS 07-299 solvent purification system) or highest anhydrous grade (used as received). Acetonitrile-d3 and acetone-d6 were used as received in 1 g ampules (Cambridge Isotope Labs). Ferrocene, tetrabutylammonioum hexafluorophosphate (TBAH), and silver nitrate were of
  • on 5a were performed on an argon-purged, ca. 24 mM solution in acetone-d6. 1D NOE spectra were collected using 400 manually interleaved scans with a 4 s relaxation delay, targeting a single peak per experiment, in a manner similar to that previously reported [21] for photogenerated 4a,b
  • photolysis (dashed orange). 1H NMR distinction between SW 3a, thermal/eLW 5a, and pLW 4a, in acetone-d6, as observed a) before and b) after photolysis. HOMO (MO 105, red and blue) and LUMO (MO 106, green and yellow) computed for 3a in its ground (S0) state. Similar results were observed for the frontier
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Published 18 Oct 2019

Indium-mediated C-allylation of melibiose

  • Christian Denner,
  • Manuel Gintner,
  • Hanspeter Kählig and
  • Walther Schmid

Beilstein J. Org. Chem. 2019, 15, 2458–2464, doi:10.3762/bjoc.15.238

Graphical Abstract
  • by TLC analysis (1-butanol/acetone/water 5:4:1, v/v/v). The reaction mixture was filtered over celite and the filtrate concentrated under reduced pressure, leaving a colorless oil. The crude material was dissolved in pyridine (10 mL) and treated with acetic anhydride (10 mL). A catalytic amount of
  • with NaOMe (pH 9) until a pH around 9 was reached. The solution was stirred at rt for 2 h, until reaction monitoring via TLC analysis (1-butanol/acetone/H2O 5:4:1, v/v/v) showed complete conversion of the starting material. The reaction mixture was diluted with dichloromethane (dichloromethane/MeOH, 1
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Published 16 Oct 2019

Reversible switching of arylazopyrazole within a metal–organic cage

  • Anton I. Hanopolskyi,
  • Soumen De,
  • Michał J. Białek,
  • Yael Diskin-Posner,
  • Liat Avram,
  • Moran Feller and
  • Rafal Klajn

Beilstein J. Org. Chem. 2019, 15, 2398–2407, doi:10.3762/bjoc.15.232

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  • was slowly added to 1,3,5-tri(1H-imidazol-1-yl)benzene (106 mg, 0.384 mmol) and the resulting mixture was stirred for 24 h at room temperature. Then, all the insoluble materials were removed by centrifugation and the supernatant was concentrated in vacuo. Crystalline 2 was obtained by acetone vapor
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Published 10 Oct 2019

1,2,3-Triazolium macrocycles in supramolecular chemistry

  • Mastaneh Safarnejad Shad,
  • Pulikkal Veettil Santhini and
  • Wim Dehaen

Beilstein J. Org. Chem. 2019, 15, 2142–2155, doi:10.3762/bjoc.15.211

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  • synthesized the novel tetra-1,2,3-triazolium zinc porphyrin cage 3 (Figure 4) and have probed its characteristics by using UV–visible spectroscopy, determining the association constants for complex formation in 5% water/acetone. This receptor has shown affinity toward all of the halide ions and especially
  • association constant of macrocycle 3 in the more competitive 15% water/acetone medium, still demonstrating a high binding affinity for sulfate anion (Ka = 2.5 × 105 M−1) while the cage 3 did not show any binding toward the other tested anions in the more aqueous solvent mixture. 2.3. Redox-active 1,2,3
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Published 12 Sep 2019

1,2,3,4-Tetrahydro-1,4,5,8-tetraazaanthracene revisited: properties and structural evidence of aromaticity loss

  • Arnault Heynderickx,
  • Sébastien Nénon,
  • Olivier Siri,
  • Vladimir Lokshin and
  • Vladimir Khodorkovsky

Beilstein J. Org. Chem. 2019, 15, 2059–2068, doi:10.3762/bjoc.15.203

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  • . For instance, the energy difference between the dication 6 and a hypothetic dication with protonated amino groups is 51 kcal/mol in favor of 6. UV–vis absorption spectra In solution, 3 is characterized by a strong absorption band, at 402 nm (toluene), 406 nm (acetone), 413 nm (water) and 422 nm
  • (ethanol) (ε ≈ 20,000). Whereas a 5 nm shift between the absorption maximum in toluene and acetone evidences the presence of slight positive solvatochromism, the band shapes in water and ethanol are irregular and reflect rather specific interaction with these solvents. The shoulder extending from 450 till
  • % yield (756 mg). 1H NMR (acetone-d6) δ 3.53 (s, 4H), 6.92 (s, 2H), 7.88 (br s, 2H), 8.33 (s, 2H); anal. calcd. for C10H12N4·2BF4: C, 33.19; H, 3.34; N, 15.48; found: C, 33.26; H, 3.22; N, 15.91. 6-Methyl-1,2,3,4-tetrahydropyrazino[2,3-g]quinoxalinium iodide (7a): A solution of 1,2,3,4-tetrahydropyrazino
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Published 28 Aug 2019

Synthesis and anion binding properties of phthalimide-containing corona[6]arenes

  • Meng-Di Gu,
  • Yao Lu and
  • Mei-Xiang Wang

Beilstein J. Org. Chem. 2019, 15, 1976–1983, doi:10.3762/bjoc.15.193

Graphical Abstract
  • ]tetrazines 3 displayed only one set of proton and carbon signals in the 1H and 13C NMR spectra, respectively, in acetone-d6 at room temperature (Figure 2). This is in sharp contradiction to O6-corona[3]arene[3]tetrazines composed of diethyl terephthalate which give several sets of resonance peaks [23][24
  • . After filtration and concentration, the residue was chromatographed on a silica gel column using a mixture of DCM and EtOAc (v/v = 100:1) as an eluent to give product 3a–e. 3a: 140 mg, yield 42%, red solid, mp 275 °C (decomp.); 1H NMR (400 MHz, acetone-d6, 25 °C) δ 8.00 (s, 6H), 7.20–7.34 (m, 15H); 13C
  • NMR (101 MHz, acetone-d6, 25 °C) δ 168.8, 164.4, 147.1, 132.2, 132.1, 129.6, 128.8, 127.5, 125.6; IR (KBr, cm−1) ν: 3078, 1777, 1724, 1494, 1384, 1230, 1115, 955; HRMS-APCI: [M + H]+ calcd for C48H22N15O12, 1000.1567; found, 1000.1553; anal. calcd for C48H21N15O12: C, 57.66; H, 2.12; N, 21.01; found
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Published 21 Aug 2019
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  • MHz instrument. Spectra were referenced to the residual solvent signals (acetone-d6, 2.05 ppm; dimethyl sulfoxide-d6, 2.50 ppm and [13C]dimethyl sulfoxide, 39.5 ppm; methanol-d4, 3.31 ppm and [13C]methanol, 49.0 ppm). NMR DOSY experiments were performed on a Varian VNMRS-600 spectrometer equipped with
  • . Analytical data are in agreement with literature data [27]. The product was obtained as yellow powder, yield: 93% (33.12 g). 1H NMR (400 MHz, acetone-d6, δ) 8.45 (s, 8H), 7.55 (s, 4H), 6.25 (s, 4H), 4.47 (t, J = 8.0 Hz, 4H), 2.17 (bt, 8H), 1.48 (m, 4H), 0.95 (d, J = 6.7 Hz, 24H). Figure S1 (Supporting
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Published 12 Aug 2019

Tautomerism as primary signaling mechanism in metal sensing: the case of amide group

  • Vera Deneva,
  • Georgi Dobrikov,
  • Aurelien Crochet,
  • Daniela Nedeltcheva,
  • Katharina M. Fromm and
  • Liudmil Antonov

Beilstein J. Org. Chem. 2019, 15, 1898–1906, doi:10.3762/bjoc.15.185

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  • , acetone-d6, acetonitrile-d3 etc.) are not informative. In all cases a complicated mixture of tautomers and lack of signals was observed. Therefore, the NMR spectra were recorded in strong basic media, in order to obtain a single tautomeric skeleton. Nevertheless, some signals in the 13C NMR spectra do
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Published 08 Aug 2019

Complexation of 2,6-helic[6]arene and its derivatives with 1,1′-dimethyl-4,4′-bipyridinium salts and protonated 4,4'-bipyridinium salts: an acid–base controllable complexation

  • Jing Li,
  • Qiang Shi,
  • Ying Han and
  • Chuan-Feng Chen

Beilstein J. Org. Chem. 2019, 15, 1795–1804, doi:10.3762/bjoc.15.173

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  •  1, Figures S1–S8). Host–guest complexation in solution Firstly, we tested the complexation between hosts H1 and H4 with guest G1 in solution by 1H NMR spectroscopy. As shown in Figure 2, when mixing equivalent amounts of host and guest in CDCl3/acetone-d6 1:2 (v/v), the 1H NMR spectrum showed a new
  • different polarity can also affect the complexation between the hosts and the guests. As shown in Table 2, we found that performing the 1H NMR titrations of the host–guest complexation in CDCl3/acetone-d6 1:2 (v/v), the Ka values of the 1:1 host–guest complexes were about 103 M−1 except for H2 that showed
  • -polar solvent, acetone hampers or competes the intermolecular non-covalent interactions between the hosts and the guests, and thus resulted in a decrease of the host–guest complexation. ESIMS studies of the formation of host–guest complexes The electrospray ionization (ESI) mass spectra also confirmed
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Published 26 Jul 2019

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

  • Iwona E. Głowacka,
  • Aleksandra Trocha,
  • Andrzej E. Wróblewski and
  • Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

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Published 23 Jul 2019

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

  • Gagandeep Kour Reen,
  • Ashok Kumar and
  • Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

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Published 19 Jul 2019

Synthesis, enantioseparation and photophysical properties of planar-chiral pillar[5]arene derivatives bearing fluorophore fragments

  • Guojuan Li,
  • Chunying Fan,
  • Guo Cheng,
  • Wanhua Wu and
  • Cheng Yang

Beilstein J. Org. Chem. 2019, 15, 1601–1611, doi:10.3762/bjoc.15.164

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  • , Supporting Information File 1. HRESIMS (m/z): [M − H]− calcd for [C26H17O]−, 345.1279; found, 345.1277. Synthesis of 5: Under nitrogen atmosphere, a mixture of compound 4 (800.0 mg, 2.3 mmol), K2CO3 (952.2 mg, 6.9 mmol) and 1,5-dibromopentane (1.1 g, 4.6 mmol) was dissolved in 30 mL dry acetone and the
  • %; ii) N-bromosuccinimide, chloroform, 60 °C, yield: 87%; iii) (4-hydroxyphenyl)boronic acid, Pd(PPh3)4, K2CO3, CsF, toluene/THF/H2O, reflux, 8 h, yield: 70%; iv) K2CO3, 1,5-dibromopentane, acetone, 80 °C, yield: 67%; v) NaN3, DMF, yield: 84%; vi) paraformaldehyde, BF3·OEt2, 1,2-dichloroethane, yield
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Published 18 Jul 2019
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