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Search for "tetrahydrofuran" in Full Text gives 303 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Recent developments in enantioselective photocatalysis

  • Callum Prentice,
  • James Morrisson,
  • Andrew D. Smith and
  • Eli Zysman-Colman

Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197

Graphical Abstract
  • enantioenriched tetrahydrofuran 256 in excellent yields and moderate enantioselectivities (14 examples, up to 82:18 er). Knowles et al. synthesised enantioenriched pyrroloindolines 257 from indoles 258 and TEMPO using an iridium-based photocatalyst and a similar chiral phosphate base 259 to that employed by Luo
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Published 29 Sep 2020

Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones

  • Viktor M. Tkachuk,
  • Oleh O. Lukianov,
  • Mykhailo V. Vovk,
  • Isabelle Gillaizeau and
  • Volodymyr A. Sukach

Beilstein J. Org. Chem. 2020, 16, 2304–2313, doi:10.3762/bjoc.16.191

Graphical Abstract
  • . Average product yields of 38–69% were observed for the reaction run in methanol, dichloroethane, tetrahydrofuran, and ethyl acetate (Table 1, entries 13–15, 20 and 21). In dimethyl carbonate and DMSO solutions, the yields were reduced to 4 and 11%, respectively (Table 1, entries 22 and 23). In contrast
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Published 17 Sep 2020

Controlling the stereochemistry in 2-oxo-aldehyde-derived Ugi adducts through the cinchona alkaloid-promoted electrophilic fluorination

  • Yuqing Wang,
  • Gaigai Wang,
  • Anatoly A. Peshkov,
  • Ruwei Yao,
  • Muhammad Hasan,
  • Manzoor Zaman,
  • Chao Liu,
  • Stepan Kashtanov,
  • Olga P. Pereshivko and
  • Vsevolod A. Peshkov

Beilstein J. Org. Chem. 2020, 16, 1963–1973, doi:10.3762/bjoc.16.163

Graphical Abstract
  • preferred reaction medium for this process with acetonitrile, tetrahydrofuran, and dichloromethane being less efficient in terms of ee of the obtained product 12a (Table 3, entries 1–5). Using catalytic quantities of quinine led to a prolonged reaction time and diminished yield and ee of 12a compared to the
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Published 11 Aug 2020

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

  • Paola Vitale,
  • Luciana Cicco,
  • Ilaria Cellamare,
  • Filippo M. Perna,
  • Antonio Salomone and
  • Vito Capriati

Beilstein J. Org. Chem. 2020, 16, 1915–1923, doi:10.3762/bjoc.16.158

Graphical Abstract
  • ][3]. As part of our ongoing research in DES chemistry, we reported recently on the preparation of valuable heterocycles by (a) nucleophilic substitution (tetrahydrofuran derivatives) [4], (b) heterocyclodehydration reactions (2-aminoimidazoles, 2-pyrazinones, benzoxazines, thiophenes) [5][6][7][8
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Published 05 Aug 2020

Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study

  • Csilla Hargitai,
  • Györgyi Koványi-Lax,
  • Tamás Nagy,
  • Péter Ábrányi-Balogh,
  • András Dancsó,
  • Gábor Tóth,
  • Judit Halász,
  • Angéla Pandur,
  • Gyula Simig and
  • Balázs Volk

Beilstein J. Org. Chem. 2020, 16, 1636–1648, doi:10.3762/bjoc.16.136

Graphical Abstract
  • under the same conditions in tetrahydrofuran (THF) instead of DCM, substantially less dimer-like product 3a or 3b was formed in favor of the rearranged aldehyde 2a or 2b. When starting from aldehyde 1c [2], containing the methoxy function in the ortho position of the formyl moiety and meta to the
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Published 13 Jul 2020

Synthesis of new dihydroberberine and tetrahydroberberine analogues and evaluation of their antiproliferative activity on NCI-H1975 cells

  • Giacomo Mari,
  • Lucia De Crescentini,
  • Serena Benedetti,
  • Francesco Palma,
  • Stefania Santeusanio and
  • Fabio Mantellini

Beilstein J. Org. Chem. 2020, 16, 1606–1616, doi:10.3762/bjoc.16.133

Graphical Abstract
  • achieved as a pure pale yellow solid directly from the reaction medium with the best yields (Table 1, entry 7). In tetrahydrofuran (THF), in ethyl acetate (EtOAc), and in alcohols such as methanol, ethanol, isopropanol (MeOH, EtOH, iPrOH) the reaction furnishes a complicate profile, where the desired 2a is
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Published 06 Jul 2020

Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers

  • Alberto Rubin Pedrazzo,
  • Fabrizio Caldera,
  • Marco Zanetti,
  • Silvia Lucia Appleton,
  • Nilesh Kumar Dhakar and
  • Francesco Trotta

Beilstein J. Org. Chem. 2020, 16, 1554–1563, doi:10.3762/bjoc.16.127

Graphical Abstract
  • extraction with acetone). Moreover, this could be also explained since not all the reactive groups are freely accessible within the NS structure. Carbonyl diimidazole can react with carboxylic acids at room temperature in many aprotic solvents (such as tetrahydrofuran, DMSO, or DMF) to form imidazolides in
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Published 29 Jun 2020

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

  • Stephanie G. E. Amos,
  • Marion Garreau,
  • Luca Buzzetti and
  • Jerome Waser

Beilstein J. Org. Chem. 2020, 16, 1163–1187, doi:10.3762/bjoc.16.103

Graphical Abstract
  • tetrahydrofuran (8.1), giving access to the key C(sp3) radical. The nickel catalyst, after an oxidative addition with the aryl bromide 8.2 and intercepting the alkyl radical species, gave the radical cross-coupling product 8.3 upon a reductive elimination. Other diaryl ketone dyes, such as 9-fluorenone, have been
  • system to perform a ring closure/pyridylation radical cascade for the synthesis of tetrahydrofuran derivatives (Scheme 39b) [161]. Eosin Y (OD13) has been demonstrated to be another competent photocatalyst for the generation of O-centered radicals from N-alkoxypyridynium salts. These radicals have been
  • , including eosin Y (OD13) [163] and acridine red [164]. Wang and co-workers relied on this approach for the development of an organophotocatalytic vinylation of tetrahydrofuran derivatives with alkynes (Scheme 40) [165]. In this method, the photoexcited OD13 induces the cleavage of the weak O–O bond of tert
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Published 29 May 2020

Synthesis and properties of quinazoline-based versatile exciplex-forming compounds

  • Rasa Keruckiene,
  • Simona Vekteryte,
  • Ervinas Urbonas,
  • Matas Guzauskas,
  • Eigirdas Skuodis,
  • Dmytro Volyniuk and
  • Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 1142–1153, doi:10.3762/bjoc.16.101

Graphical Abstract
  • polarities, i.e., toluene (0.099), tetrahydrofuran (0.207) and dimethylformamide (0.4) (values in parentheses are the solvent polarities relative to water) [21]. The PL spectra of the solutions of compound 3 appeared to be solvent-polarity independent as only the structured emission band of the locally
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Published 28 May 2020

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

  • Nuray Altinolcek,
  • Ahmet Battal,
  • Mustafa Tavasli,
  • William J. Peveler,
  • Holly A. Yu and
  • Peter J. Skabara

Beilstein J. Org. Chem. 2020, 16, 1066–1074, doi:10.3762/bjoc.16.93

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  • either with 2-bromopyridine-4-carbaldehyde (6a) or 2-bromopyridine-5-carbaldehyde (6b) in the presence of potassium carbonate and bis(triphenylphosphine)palladium(II) dichloride in tetrahydrofuran [2]. Upon repeated purification by chromatography, compounds 7a and 7b were obtained as liquids in good
  • pinacol ester (5, 447 mg, 1.2 mmol), 2-bromopyridine-4-carbaldehyde (6a, 147 mg, 0.8 mmol), potassium carbonate (1 M, 9.6 mL) and dichlorobis(triphenylphosphine)palladium(II) (40 mg, 0.06 mmol) were dissolved in tetrahydrofuran (20 mL). The reaction mixture was refluxed for 24 h under an argon atmosphere
  • (triphenylphosphine)palladium(II) (13 mg, 0.02 mmol) were dissolved in tetrahydrofuran (10 mL). The reaction mixture was refluxed for 6 h under an argon atmosphere. After removing the solvent, the crude product was dissolved in dichloromethane and washed with water (3 × 20 mL). The combined extracts were dried over
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Published 19 May 2020

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

  • Rodrigo Costa e Silva,
  • Luely Oliveira da Silva,
  • Aloisio de Andrade Bartolomeu,
  • Timothy John Brocksom and
  • Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

Graphical Abstract
  • ). For an oxidative quenching, the photoarylation of heteroarenes and alkynes with aryldiazonium salts, and the oxidative decarboxylative coupling between cinnamic acid and tetrahydrofuran also showed better results when NiTPP was used instead of eosin [32][33][34] (Scheme 10). Regarding protocols
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Published 06 May 2020

Diversity-oriented synthesis of 17-spirosteroids

  • Benjamin Laroche,
  • Thomas Bouvarel,
  • Martin Louis-Sylvestre and
  • Bastien Nay

Beilstein J. Org. Chem. 2020, 16, 880–887, doi:10.3762/bjoc.16.79

Graphical Abstract
  • imposed by the steroid skeleton on the dienyl tetrahydrofuran α-face, imposing orbital interactions with the dienophile from the β-face (Figure 3b). All these structures have an extended skeleton, with the steroid part being perpendicular to the cycloadduct moiety thanks to the spiro junction. Conclusion
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Published 28 Apr 2020

One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation

  • Ji Ma,
  • Yubin Fu,
  • Junzhi Liu and
  • Xinliang Feng

Beilstein J. Org. Chem. 2020, 16, 791–797, doi:10.3762/bjoc.16.72

Graphical Abstract
  • solvents, such as dichloromethane, chloroform, tetrahydrofuran and toluene, allowing a full characterization by NMR analyses. Finally, the palladium-catalyzed cyclopentannulation of compound 5 with 1,2-diphenylethyne under microwave conditions using the catalyst system of [Pd2(dba)3] and P(o-tol)3 afforded
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Published 20 Apr 2020

Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules

  • Valerian Dragutan,
  • Ileana Dragutan,
  • Albert Demonceau and
  • Lionel Delaude

Beilstein J. Org. Chem. 2020, 16, 738–755, doi:10.3762/bjoc.16.68

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  • stereoselective formation of the tetrahydrofuran rings. Conclusion This review highlighted the most recent efforts regarding the development of enyne metathesis-based syntheses of complex bioactive, natural and nonnatural organic molecules. Both, intra- and intermolecular enyne metatheses have been valorized to
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Published 16 Apr 2020

Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas

  • Zhenghui Liu,
  • Peng Wang,
  • Zhenzhong Yan,
  • Suqing Chen,
  • Dongkun Yu,
  • Xinhui Zhao and
  • Tiancheng Mu

Beilstein J. Org. Chem. 2020, 16, 645–656, doi:10.3762/bjoc.16.61

Graphical Abstract
  • (PMP)), and solvents (N,N-dimethylacetamide (DMA), 1,3-dimethyl-2-imidazolidinone (DMI), N-methyl-2-pyrrolidinone (NMP), tetrahydrofuran (THF), 1,4-dioxane, ethanol, methanol, acetonitrile, and toluene) together with aryl iodides and other reagents were purchased from commercial sources (namely J&K
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Published 08 Apr 2020

Design and synthesis of diazine-based panobinostat analogues for HDAC8 inhibition

  • Sivaraman Balasubramaniam,
  • Sajith Vijayan,
  • Liam V. Goldman,
  • Xavier A. May,
  • Kyra Dodson,
  • Sweta Adhikari,
  • Fatima Rivas,
  • Davita L. Watkins and
  • Shana V. Stoddard

Beilstein J. Org. Chem. 2020, 16, 628–637, doi:10.3762/bjoc.16.59

Graphical Abstract
  • designed analogues and evaluating their overall potential to inhibit neuroblastoma cell growth. Experimental General Reagents and solvents were purchased from commercial sources and used without further purification unless otherwise specified. Tetrahydrofuran (THF), ether, dichloromethane (DCM), and
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Published 07 Apr 2020

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

  • Pezhman Shiri and
  • Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

Graphical Abstract
  • reacted with 4-aminomethylpiperidine (AMP, 21) or piperazine (PIP) to afford G1-AAA–SBA-15 (G1-AMP–SBA-15, 22, or G2-PIP–SBA-15, 23) materials (Scheme 3). The resulting solid product was then filtrated and washed with methanol, dichloromethane, and tetrahydrofuran. The organic part of the G1-AAA–SBA-15
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Published 01 Apr 2020

Aerobic synthesis of N-sulfonylamidines mediated by N-heterocyclic carbene copper(I) catalysts

  • Faïma Lazreg,
  • Marie Vasseur,
  • Alexandra M. Z. Slawin and
  • Catherine S. J. Cazin

Beilstein J. Org. Chem. 2020, 16, 482–491, doi:10.3762/bjoc.16.43

Graphical Abstract
  • (see Supporting Information File 1 for details). Tetrahydrofuran (THF), 1,2-DCE, 1,4-dioxane and acetonitrile proved to be the most suitable solvents for this transformation (Table 1). Interestingly, similar results were obtained for complexes 1–5, while 6 displayed superior activity. Indeed, 71
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Published 24 Mar 2020

Architecture and synthesis of P,N-heterocyclic phosphine ligands

  • Wisdom A. Munzeiwa,
  • Bernard Omondi and
  • Vincent O. Nyamori

Beilstein J. Org. Chem. 2020, 16, 362–383, doi:10.3762/bjoc.16.35

Graphical Abstract
  • ]. Thus, the diphosphine ligand 51 was obtained in good yield by reacting 2,6-bis(chloromethyl)pyridine (50) with phosphine lithiothiolate 49. The latter was obtained by treatment of diphenylphosphine (48) with n-BuLi and ethylene sulfide in tetrahydrofuran at very low temperatures. Metal–proton exchange
  • protocol with free amine spiro-amino alcohol derivative 124 gave compounds 125 and 127 (R = H) in low yields. An optimized procedure was used where dichlorophenylphosphine and borane·dimethyl sulfide in tetrahydrofuran were premixed at −78 °C. The temperature was then raised to 25 °C before neutralizing
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Published 12 Mar 2020

p-Pyridinyl oxime carbamates: synthesis, DNA binding, DNA photocleaving activity and theoretical photodegradation studies

  • Panagiotis S. Gritzapis,
  • Panayiotis C. Varras,
  • Nikolaos-Panagiotis Andreou,
  • Katerina R. Katsani,
  • Konstantinos Dafnopoulos,
  • George Psomas,
  • Zisis V. Peitsinis,
  • Alexandros E. Koumbis and
  • Konstantina C. Fylaktakidou

Beilstein J. Org. Chem. 2020, 16, 337–350, doi:10.3762/bjoc.16.33

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  • + 12 + CR (200 μM) + UV. Synthesis of O-carbamoyl amidoximes (8–13), ethanone oximes (15–20) and aldoximes (22–27). Oxime 1 or 14 or 21, Et3N (1.1 equiv), R–NCO (1.1–1.8 equiv), dry chloroform or tetrahydrofuran, Ar, 0 °C → rt or reflux, 19–97%. Photodissociation reaction of the derivative 12 in the T1
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Published 09 Mar 2020

Halogen-bonding-induced diverse aggregation of 4,5-diiodo-1,2,3-triazolium salts with different anions

  • Xingyu Xu,
  • Shiqing Huang,
  • Zengyu Zhang,
  • Lei Cao and
  • Xiaoyu Yan

Beilstein J. Org. Chem. 2020, 16, 78–87, doi:10.3762/bjoc.16.10

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  • good yield (Scheme 1). The product 2-I was characterized by 1H NMR, 13C NMR, and high-resolution mass spectrometry. 2-I has a poor solubility in most organic solvents such as dichloromethane, trichloromethane, tetrahydrofuran, and ethanol. A single crystal of 2-I was obtained by slow diffusion of ether
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Published 13 Jan 2020

Photoreversible stretching of a BAPTA chelator marshalling Ca2+-binding in aqueous media

  • Aurélien Ducrot,
  • Arnaud Tron,
  • Robin Bofinger,
  • Ingrid Sanz Beguer,
  • Jean-Luc Pozzo and
  • Nathan D. McClenaghan

Beilstein J. Org. Chem. 2019, 15, 2801–2811, doi:10.3762/bjoc.15.273

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  • MHz) or an Avance 300 (1H: 300 MHz, 13C: 75 MHz) spectrometer. Chemical shifts are reported in ppm (δ) and are referenced to the NMR solvent residual peaks. Abbreviations used are s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet. Reagent grade tetrahydrofuran (THF) was distilled under
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Published 21 Nov 2019

An improved, scalable synthesis of Notum inhibitor LP-922056 using 1-chloro-1,2-benziodoxol-3-one as a superior electrophilic chlorinating agent

  • Nicky J. Willis,
  • Elliott D. Bayle,
  • George Papageorgiou,
  • David Steadman,
  • Benjamin N. Atkinson,
  • William Mahy and
  • Paul V. Fish

Beilstein J. Org. Chem. 2019, 15, 2790–2797, doi:10.3762/bjoc.15.271

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  • . Yields are the ranges obtained from repeated reactions. DMF, N,N-dimethylformamide; NBS, N-bromosuccinimide; THF, tetrahydrofuran. Chlorination of 6 with N-chlorosuccinimide (NCS). Reagents and conditions: (a) NCS (1.2 equiv), AcOH, 55 °C, 7 h, 15–32%. Improved synthesis of 5. Reagents and conditions: (a
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Published 19 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
  • emission band with a maximum at 401, 442, and 420 nm, in acetonitrile, respectively. These are tentatively assigned to π–π* transitions of the variable aryl moiety. Interestingly, in tetrahydrofuran, containing oxygen as donor atom, only the SW emission band is seen, i.e., λfluo,max = 409 nm (16), 402 nm
  • LW band is substituted by a strong blue-shifted emission. This leads to a clear ratiometric behavior and a large dynamic response. The blue-shifted emission for the fluoroboronate Lewis adduct is in accordance with the observations made for donor solvents such as tetrahydrofuran (see above). As for
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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
  • yield a new cation, which in turn is nucleophilically trapped by the carbinol moiety. The resulting tetrahydrofuran 59 is chemically stable and this observation was used as rationale for the erosion of the isomeric ratio observed during prolonged reaction times. In the same piece of work Fráter et al
  • Plus® (34). Products 58 (α double bond) and product 53 (β double bond) are not desired [26]. Iso E Super Plus® (34) can undergo a third cyclisation to tetrahydrofuran 59 through compound rac-53 [22]. New unnatural terpenoid 70 from unnatural farnesyl pyrophosphate derivative 69 and comparison with
  • natural biotransformation (67→68) and olfactory property of tetrahydrofuran 70 [39]. Individual components of the complex Iso E Super® mixture. Top fragrances with regard to their volume percentage (listed down to about 20%; the large number of perfumes with lower percentages are not listed) of Iso E
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Published 31 Oct 2019
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