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Search for "tetrahydrofuran" in Full Text gives 307 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor

  • Yuki Naito,
  • Naoki Shida and
  • Mahito Atobe

Beilstein J. Org. Chem. 2022, 18, 350–359, doi:10.3762/bjoc.18.39

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  • electrodes and subjected to the electrolytic reaction. Tetrahydrofuran (THF), which is easily oxidized, was employed as the electrolytic solvent, so the reaction at the anode (counter electrode) is thought to be preferentially caused by the oxidative decomposition of THF, and the re-oxidation of the cathodic
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Published 29 Mar 2022

Synthesis and late stage modifications of Cyl derivatives

  • Phil Servatius and
  • Uli Kazmaier

Beilstein J. Org. Chem. 2022, 18, 174–181, doi:10.3762/bjoc.18.19

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  • , we treated 11 with thioacetic acid and BEt3/air in THF to give 82% of the thiol-ene click product (Scheme 4). Careful analysis of the NMR spectra revealed that the intermediately formed radical cyclized in an intramolecular 5-exo-trig fashion with the internal double bond to form a tetrahydrofuran
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Published 04 Feb 2022

Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction

  • Irina Kuznetcova,
  • Felix Bacher,
  • Daniel Vegh,
  • Hsiang-Yu Chuang and
  • Vladimir B. Arion

Beilstein J. Org. Chem. 2022, 18, 143–151, doi:10.3762/bjoc.18.15

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  • steps as shown in Scheme 3. First, reduction of commercially available indole-2-carboxylate with lithium aluminum hydride in dry tetrahydrofuran gave (1H-indole-2-yl)methanol (10) in 89% yield. The obtained alcohol was exposed to benzoyl chloride and triethylamine to furnish benzoate 11, which was
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Published 26 Jan 2022

Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes

  • Nicolai Wippert,
  • Martin Nieger,
  • Claudine Herlan,
  • Nicole Jung and
  • Stefan Bräse

Beilstein J. Org. Chem. 2021, 17, 2773–2780, doi:10.3762/bjoc.17.187

Graphical Abstract
  • , failed under similar procedures. Abbreviations TFA, trifluoroacetic acid; DMSO, dimethyl sulfoxide; THF, tetrahydrofuran, TLC, thin-layer chromatography, LC–MS, liquid chromatography/mass spectrometry. Structural differences of several known (2–4) and so far unknown (5 and 6) pyrazolo[3,4-d][1,2,3]-3H
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Published 22 Nov 2021

In-depth characterization of self-healing polymers based on π–π interactions

  • Josefine Meurer,
  • Julian Hniopek,
  • Johannes Ahner,
  • Michael Schmitt,
  • Jürgen Popp,
  • Stefan Zechel,
  • Kalina Peneva and
  • Martin D. Hager

Beilstein J. Org. Chem. 2021, 17, 2496–2504, doi:10.3762/bjoc.17.166

Graphical Abstract
  • °C for 17 h. After cooling to room temperature, water and chloroform were added to the mixture. The organic phase was washed two times with water, dried over sodium sulfate and concentrated. The residual was dissolved in tetrahydrofuran and dialyzed for three days with solvent exchange two times per
  • to the mixture. The organic phase was washed two times with water and one time with brine, dried over sodium sulfate and concentrated. The residual was dissolved in a 1:1 mixture of chloroform and tetrahydrofuran and dialyzed for two days with solvent exchange two times per day (MWCO: 3500 g/mol
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Published 29 Sep 2021

Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation

  • Azra Kocaarslan,
  • Zafer Eroglu,
  • Önder Metin and
  • Yusuf Yagci

Beilstein J. Org. Chem. 2021, 17, 2477–2487, doi:10.3762/bjoc.17.164

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  • system equipped with an auto sampler system, a temperature-controlled pump, a column oven, a refractive index (RI) detector, a purge and degasser unit and a TSKgel superhZ2000, 4.6 mm ID × 15 cm × 2cm column. Tetrahydrofuran was used as an eluent at a flow rate of 1.0 mL/min at 40 °C. The refractive index
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Published 23 Sep 2021

Strategies for the synthesis of brevipolides

  • Yudhi D. Kurniawan and
  • A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

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  • comprehensive combination of quantum mechanical calculations and experimental spectroscopic analysis of their NMR and ECD data, to have a unique tetrahydrofuran ring instead of the cyclopropane functionality. The absolute configuration of these five compounds were evaluated and all conserved as C6R, C1’S, C2’R
  • (13) Sabitha and Raju demonstrated the first total synthesis of brevipolide M (13) in 2017 [17]. In the retrosynthesis, compound 93 is hypothesized from the Mitsunobu inversion at the C6’ stereocenter with (E)-p-methoxycinnamic acid (17) and ring-closing metathesis of tetrahydrofuran 93 (Scheme 11
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Published 14 Sep 2021

Advances in mercury(II)-salt-mediated cyclization reactions of unsaturated bonds

  • Sumana Mandal,
  • Raju D. Chaudhari and
  • Goutam Biswas

Beilstein J. Org. Chem. 2021, 17, 2348–2376, doi:10.3762/bjoc.17.153

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  • effect of H2O (protic solvent) in the reaction media [48]. Pulido et al. had developed a conversion of allylsilyl alcohols 19 to diastereomeric mixtures of tetrahydrofuran derivatives 20A and 20B (Scheme 9) [47]. It was reported that more substituted alkyl groups present in allylsilyl alcohol 20b direct
  • . Synthesis of β-ᴅ-arabinose derivative 18. Hg(OAc)2-mediated synthesis of tetrahydrofuran derivatives. Synthesis of Hg(TFA)2-mediated bicyclic nucleoside derivative. Synthesis of pyrrolidine and piperidine derivatives. HgCl2-mediated synthesis of diastereomeric pyrrolidine derivatives. HgCl2-mediated
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Published 09 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
  • ) hydroxylamine hydrochloride (21 mg, 0.300 mmol) was added. A clear solution was obtained shortly thereafter. The reaction was stirred for two hours at room temperature. Tetrahydrofuran (4 mL) and damp Raney-Nickel (approximately 200 mg) were introduced and the reaction was continued for one hour. The reaction
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Published 02 Sep 2021

Photoredox catalysis in nickel-catalyzed C–H functionalization

  • Lusina Mantry,
  • Rajaram Maayuri,
  • Vikash Kumar and
  • Parthasarathy Gandeepan

Beilstein J. Org. Chem. 2021, 17, 2209–2259, doi:10.3762/bjoc.17.143

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  • photoredox nickel-catalyzed arylation of α-oxy C–H bonds of tetrahydrofuran (THF) and oxetane were also shown. Further, the catalytic system also proved compatible for the C‒H arylation of the benzylic system. As shown in Figure 2 [54], the mechanism for the transformation is proposed to involve the
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Published 31 Aug 2021

Chemical syntheses and salient features of azulene-containing homo- and copolymers

  • Vijayendra S. Shetti

Beilstein J. Org. Chem. 2021, 17, 2164–2185, doi:10.3762/bjoc.17.139

Graphical Abstract
  • on the elemental analysis, the authors provided the formula representation C10H6(I2)0.4 for PAZ-I2 and C10H4.9(Br2)0.72 for PAZ-Br2. The gel permeation chromatography (GPC) analysis of the tetrahydrofuran (THF)-soluble fraction of PAZ-Br2 indicated the presence of oligomeric species (average degree
  • polyazulene 3 or 3’ was soluble in various organic solvents such as toluene, dichloromethane, tetrahydrofuran (THF), and N,N’-dimethylformamide (DMF). The ‘true polyazulene’ exhibited the conductivity of 5.38 × 10−8 S/cm, which was increased to 8.16 × 10−3 S/cm upon exposure to iodine atmosphere, presumably
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Published 24 Aug 2021

Constrained thermoresponsive polymers – new insights into fundamentals and applications

  • Patricia Flemming,
  • Alexander S. Münch,
  • Andreas Fery and
  • Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

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Published 20 Aug 2021

Regioselective N-alkylation of the 1H-indazole scaffold; ring substituent and N-alkylating reagent effects on regioisomeric distribution

  • Ryan M. Alam and
  • John J. Keating

Beilstein J. Org. Chem. 2021, 17, 1939–1951, doi:10.3762/bjoc.17.127

Graphical Abstract
  • alkylindazoles. Initial screening of various conditions revealed that the combination of sodium hydride (NaH) in tetrahydrofuran (THF) (in the presence of an alkyl bromide), represented a promising system for N-1 selective indazole alkylation. For example, among fourteen C-3 substituted indazoles examined, we
  • electrophiles, while maintaining a high degree of N-1 regioselectivity. Keywords: indazole; N-alkylation; regioselective; sodium hydride; tetrahydrofuran; Introduction Indazole (benzo[c]pyrazole) is an aromatic bicyclic heterocycle and can be viewed as a (bio)isostere of indole [1]. While only a few naturally
  • 1H-indazole, employing NaHMDS in tetrahydrofuran (THF) or dimethyl sulfoxide (DMSO), and observed solvent-dependent regioselectivity [24]. Mechanistic hypotheses, based on elegant experimentation, were proposed to underline the roles that tight and solvent-separated ion pairs played in the observed
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Published 02 Aug 2021

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

  • Renato L. Carvalho,
  • Amanda S. de Miranda,
  • Mateus P. Nunes,
  • Roberto S. Gomes,
  • Guilherme A. M. Jardim and
  • Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

Graphical Abstract
  • site-selective C(sp3)−H bond functionalization strategy (Scheme 28B) [160]. Starting from the abundant feedstock chemical cedrol, oxidation of the gem-dimethyl group was achieved on a gram scale, with the formation of a strained tetrahydrofuran ring. The latter was methylated and eliminated via the
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Published 30 Jul 2021

Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs

  • Jongwoo Son

Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122

Graphical Abstract
  • fluorine activation (see 22i–j), and the oxygen-containing natural terpenoid ambroxide was methylated at the methylene position next to the O atom on the tetrahydrofuran ring (see 22k). This manganese-catalyzed late-stage approach enables the direct methylation of unactivated C–H bonds with excellent site
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Published 26 Jul 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
  • enantioselectivities. A similar enantioselectivity was attained in α,α,α-trifluorotoluene and tetrahydrofuran as the solvent, whereas in chloroform a slightly improved enantioselectivity of 86% ee was observed. Finally, the best solvent was found to be 1,2-dichloroethane and the product 3a was obtained in 82% yield
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Published 14 Jun 2021

Double-headed nucleosides: Synthesis and applications

  • Vineet Verma,
  • Jyotirmoy Maity,
  • Vipin K. Maikhuri,
  • Ritika Sharma,
  • Himal K. Ganguly and
  • Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

Graphical Abstract
  • -isobutyrylguanine, N-benzoylcytosine, 6-O-allylhypoxanthine or N,N-dibenzoyldiaminopurine in 53 to 83% yield. The desilylation of the nucleosides 3a–f with tetrabutylammonium fluoride in tetrahydrofuran (THF) led to the formation of six different double-headed nucleosides 4a–f (Scheme 1) [38][39]. The synthesized
  • (Scheme 17) [54]. The tert-butyldimethylsilyl-protected (TBDMS) nucleoside 76 was first hydrolyzed using NaOH, which was followed by TBDMS deprotection using tetra-n-butylammonium fluoride (TBAF) in tetrahydrofuran (THF) to afford the double-headed nucleoside 77. The TBDMS-protected nucleoside 73 was
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Published 08 Jun 2021

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

  • Joseane A. Mendes,
  • Paulo R. R. Costa,
  • Miguel Yus,
  • Francisco Foubelo and
  • Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

Graphical Abstract
  • from the condensation reaction of aldehydes or ketones with tert-butanesulfinamides. In this work, the condensation with aldehydes was carried using Ti(OEt)4 in tetrahydrofuran (THF), or CuSO4 in dichloromethane at room temperature. The combination of MgSO4 in the presence of a catalytic amount of
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Published 12 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
  • lines [59]. The synthesis was based on the reaction of commercially available aromatic amines with sodium dicyandiamide at 80 °C to obtain the corresponding aryldicyanoamides. The latter were then separately reacted with alkylamines or cycloalkylamines at 40 °C in tetrahydrofuran in the presence of
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Published 05 May 2021

Prins cyclization-mediated stereoselective synthesis of tetrahydropyrans and dihydropyrans: an inspection of twenty years

  • Asha Budakoti,
  • Pradip Kumar Mondal,
  • Prachi Verma and
  • Jagadish Khamrai

Beilstein J. Org. Chem. 2021, 17, 932–963, doi:10.3762/bjoc.17.77

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  • 1,3-diaxial interaction, which favors the formation of tetrahydrofuran product 17 instead of the tetrahydropyran 16 (Scheme 4). Although the Prins cyclization is one of the powerful tools for the construction of 2,6-disubstituted THPs, there are some limitations that restrict a wide applicability. The
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Published 29 Apr 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

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Published 28 Apr 2021

Synthesis and properties of oligonucleotides modified with an N-methylguanidine-bridged nucleic acid (GuNA[Me]) bearing adenine, guanine, or 5-methylcytosine nucleobases

  • Naohiro Horie,
  • Takao Yamaguchi,
  • Shinji Kumagai and
  • Satoshi Obika

Beilstein J. Org. Chem. 2021, 17, 622–629, doi:10.3762/bjoc.17.54

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  • acetonitrile, dichloromethane, and tetrahydrofuran (THF) were used as purchased. 1H, 13C, and 31P NMR spectra were recorded using a JEOL JNM-ECS300 spectrometer. The chemical shift values are expressed in δ values (ppm) relative to tetramethylsilane as an internal standard, CHCl3 (δ = 7.26 ppm) for 1H NMR
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Published 04 Mar 2021

Valorisation of plastic waste via metal-catalysed depolymerisation

  • Francesca Liguori,
  • Carmen Moreno-Marrodán and
  • Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

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  • chirality of lactic acid, three forms of PLA (ʟ, PLLA; ᴅ, PDLA; ᴅʟ, PDLLA) with slightly different properties (crystallinity, Tg 60–65 °C, Tm 130–180 °C) exist [256]. PLA is soluble in benzene, tetrahydrofuran, ethyl acetate, propylene carbonate and dioxane [257], and it is biodegradable [258][259]. Because
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Published 02 Mar 2021

Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system

  • Yamato Fujihira,
  • Yumeng Liang,
  • Makoto Ono,
  • Kazuki Hirano,
  • Takumi Kagawa and
  • Norio Shibata

Beilstein J. Org. Chem. 2021, 17, 431–438, doi:10.3762/bjoc.17.39

Graphical Abstract
  • effect on the yield of the reaction of 1g (Table 2, entries 3–6, 58–72%). Next, a range of common oxygen and sulfur-containing compounds such as furan, tetrahydrofuran, 1,4-dioxane, thiophene, benzo[b]thiophene, dibenzo[b,d]thiophene, and diphenylsulfane were also screened. These substances also have
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Published 12 Feb 2021

Synthesis, crystal structures and properties of carbazole-based [6]helicenes fused with an azine ring

  • Daria I. Tonkoglazova,
  • Anna V. Gulevskaya,
  • Konstantin A. Chistyakov and
  • Olga I. Askalepova

Beilstein J. Org. Chem. 2021, 17, 11–21, doi:10.3762/bjoc.17.2

Graphical Abstract
  • alternating enantiomers form a screw along the a axis. Optical properties All helicenes 10 are well soluble in dichloromethane and chloroform. Solubility in other common solvents such as acetonitrile, DMSO, tetrahydrofuran, ethanol and hexane is markedly lower. Carbazole-based [6]helicene 12 was described as
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Published 04 Jan 2021
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