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Search for "thionyl chloride" in Full Text gives 87 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis of a novel category of pseudo-peptides using an Ugi three-component reaction of levulinic acid as bifunctional substrate, amines, and amino acid-based isocyanides

  • Maryam Khalesi,
  • Azim Ziyaei Halimehjani and
  • Jürgen Martens

Beilstein J. Org. Chem. 2019, 15, 852–857, doi:10.3762/bjoc.15.82

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  • esterification of the α-amino acid using thionyl chloride in methanol as reagent and solvent. The second reaction is the formylation of the corresponding amino acid ester salt with ethyl formate in the presence of NaHCO3. Finally, the formamide group was transformed to the corresponding isocyanide 3 using POCl3
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Published 04 Apr 2019

Azologization of serotonin 5-HT3 receptor antagonists

  • Karin Rustler,
  • Galyna Maleeva,
  • Piotr Bregestovski and
  • Burkhard König

Beilstein J. Org. Chem. 2019, 15, 780–788, doi:10.3762/bjoc.15.74

Graphical Abstract
  • (18) [75]. Activation using thionyl chloride [76] afforded the acid chloride 26 and allowed amide-bond formation [77] for the generation of 28 (Scheme 6). Photochromic properties The investigation of the photochromic properties of the potential 5-HT3R antagonists 5a, 5b, 12a, 16a–d, 23, and 28 was
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Published 25 Mar 2019

Chiral bisoxazoline ligands designed to stabilize bimetallic complexes

  • Deepankar Das,
  • Rudrajit Mal,
  • Nisha Mittal,
  • Zhengbo Zhu,
  • Thomas J. Emge and
  • Daniel Seidel

Beilstein J. Org. Chem. 2018, 14, 2002–2011, doi:10.3762/bjoc.14.175

Graphical Abstract
  • shown in Scheme 3. In addition to the change in geometry, compound 25-H3 is a potentially trianionic as opposed to a dianionic ligand. A reaction of pyrazole-3,5-diacyl chloride 23, obtained by treatment of pyrazol-3,5-dicarboxylic acid with thionyl chloride, with aminophenyloxazoline 24 [59] provided
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Published 01 Aug 2018

First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones

  • Grzegorz Mlostoń,
  • Katarzyna Urbaniak,
  • Paweł Urbaniak,
  • Anna Marko,
  • Anthony Linden and
  • Heinz Heimgartner

Beilstein J. Org. Chem. 2018, 14, 1834–1839, doi:10.3762/bjoc.14.156

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  • treatment of quinizarine with thionyl chloride according to the protocol described in [27]. Thiochalcones 1a–d were prepared according to our protocol reported in an earlier publication [16]. General procedure: A solution of 1 mmol of the corresponding thiochalcone 1 and 1 mmol of the 1,4-quinone 2 in 1 mL
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Published 19 Jul 2018

Design, synthesis and structure of novel G-2 melamine-based dendrimers incorporating 4-(n-octyloxy)aniline as a peripheral unit

  • Cristina Morar,
  • Pedro Lameiras,
  • Attila Bende,
  • Gabriel Katona,
  • Emese Gál and
  • Mircea Darabantu

Beilstein J. Org. Chem. 2018, 14, 1704–1722, doi:10.3762/bjoc.14.145

Graphical Abstract
  • )alkanoic acid-based tripodal melamines into the corresponding tri acid chlorides (not depicted in Scheme 4) followed typical procedures (in refluxing thionyl chloride with SO2 and HCl generation), a long reaction time (up to 24 h, as determined by HRMS monitoring) was mandatory for this transformation to
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Published 09 Jul 2018

An unusual thionyl chloride-promoted C−C bond formation to obtain 4,4'-bipyrazolones

  • Gernot A. Eller,
  • Gytė Vilkauskaitė,
  • Algirdas Šačkus,
  • Vytas Martynaitis,
  • Ashenafi Damtew Mamuye,
  • Vittorio Pace and
  • Wolfgang Holzer

Beilstein J. Org. Chem. 2018, 14, 1287–1292, doi:10.3762/bjoc.14.110

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  • of 5-hydroxypyrazole-4-carboxylates in refluxing thionyl chloride. The obtained diesters can be transformed into the corresponding 4,4'-bipyrazoles via alkaline hydrolysis and subsequent decarboxylation. Detailed NMR spectroscopic investigations (1H, 13C, 15N) were undertaken with all products
  • prepared. Moreover, the structure of a representative 5,5'-dioxo-4,4'-bipyrazole-4,4'-dicarboxylate was confirmed by X-ray crystal structure analysis. Keywords: dimerization; NMR (1H; 13C; 15N); pyrazolones; thionyl chloride; X-ray structure analysis; Introduction Many biologically active substances
  • = H, R = Et) with POCl3 left the starting material untouched, similarly by treatment of 1a with oxalyl chloride no conversion occurred (Scheme 2). In contrast, treatment of 1a with excessive thionyl chloride at reflux temperature resulted in a defined reaction product which, however, could not be the
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Published 04 Jun 2018

One hundred years of benzotropone chemistry

  • Arif Dastan,
  • Haydar Kilic and
  • Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

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Published 23 May 2018

Preparation, structure, and reactivity of bicyclic benziodazole: a new hypervalent iodine heterocycle

  • Akira Yoshimura,
  • Michael T. Shea,
  • Cody L. Makitalo,
  • Melissa E. Jarvi,
  • Gregory T. Rohde,
  • Akio Saito,
  • Mekhman S. Yusubov and
  • Viktor V. Zhdankin

Beilstein J. Org. Chem. 2018, 14, 1016–1020, doi:10.3762/bjoc.14.87

Graphical Abstract
  • -iodoisophthalic acid (2). Firstly, 2-iodoisophthalic acid (2) was converted to the corresponding acyl chloride 8 by treatment with thionyl chloride (Scheme 2). In the second step, acyl chloride 8 reacted with appropriate alkylamines to give the corresponding 2-iodo-N,N’-dialkylisophthalamides 6 in good yields
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Published 08 May 2018

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

  • Ranjana Aggarwal and
  • Suresh Kumar

Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15

Graphical Abstract
  • pyridine to give 1,3,6-trisubstitutedpyrazolo[3,4-b]pyrazine-5-carbonitriles 230 in good yields. 5-Carbonitrilepyrazolo[3,4-b]pyrazines 230 were hydrolyzed to corresponding pyrazolo[3,4-b]pyrazine-5-carboxylic acids 231 and subsequently converted to acid chloride 232 at reflux temperature with thionyl
  • chloride (SOCl2) which underwent intramolecular Friedel–Crafts reaction in presence of Lewis acid to give 3-methyl-1-phenyl-1H-indeno[2,1-e]pyrazolo[3,4-b]pyrazin-5-one (233). Compound 233 was used to synthesize several other indenopyrazolopyrazinone derivatives by reaction with active methylene compounds
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Published 25 Jan 2018

Photocatalytic formation of carbon–sulfur bonds

  • Alexander Wimmer and
  • Burkhard König

Beilstein J. Org. Chem. 2018, 14, 54–83, doi:10.3762/bjoc.14.4

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  • disulfide, thioamide derivatives and sulfides Disulfides and thiosulfates Sulfoxides Sulfinic acids, sulfinate salts and sulfinamides Sulfonyl halides, sulfonyl hydrazines, thionyl chloride and sulfur dioxide C–S bond formations initiated by irradiation with light of wavelengths shorter than 380 nm or by
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Published 05 Jan 2018

Hydrolysis, polarity, and conformational impact of C-terminal partially fluorinated ethyl esters in peptide models

  • Vladimir Kubyshkin and
  • Nediljko Budisa

Beilstein J. Org. Chem. 2017, 13, 2442–2457, doi:10.3762/bjoc.13.241

Graphical Abstract
  • was cooled down in an ice bath. Thionyl chloride (0.1 mL, 1.38 mmol, 2.2 equiv) was added, followed by 2-fluoroethanol (80 μl, 1.38 mmol, 2.2 equiv). The mixture was stirred at ambient temperature for 14 hours. The solvent was removed under reduced pressure, and the resulting crude material was
  • subjected to a silica gel (20 g) column purification using an ethyl acetate/methanol 39:1 eluent. 55 mg of 3 was obtained as a clear oil (yield 42%), Rf = 0.63 (ethyl acetate/methanol 39:1). Compound 5 was obtained in an analogous procedure to 3 starting from N-acetylproline (100 mg, 0.64 mmol), thionyl
  • chloride (0.1 mL, 1.4 mmol, 2.2 equiv) and trifluoroethanol (0.12 mL, 1.6 mmol, 2.5 equiv). 141 mg of the product was obtained as a clear oil (yield 93%), Rf = 0.73 (ethyl acetate/methanol 39:1). Esterification with diazoalkanes No special precautions were applied when working with 2,2-difluorodiazoethane
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Published 16 Nov 2017

Intramolecular glycosylation

  • Xiao G. Jia and
  • Alexei V. Demchenko

Beilstein J. Org. Chem. 2017, 13, 2028–2048, doi:10.3762/bjoc.13.201

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  • application, glycosyl donor precursors were reacted with phthalic anhydride to afford the corresponding esters. The activation with thionyl chloride was used for tethering the donors to the glycosyl acceptor counterpart and the regioselectivity was controlled using tin-mediated coupling under microwave
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Published 29 Sep 2017

A novel approach to oxoisoaporphine alkaloids via regioselective metalation of alkoxy isoquinolines

  • Benedikt C. Melzer and
  • Franz Bracher

Beilstein J. Org. Chem. 2017, 13, 1564–1571, doi:10.3762/bjoc.13.156

Graphical Abstract
  • to increase the yield. As described above, attempted direct intramolecular Friedel–Crafts-type cyclization of 10c catalyzed by trifluoromethanesulfonic acid [25] failed completely. Also, generation of an acid chloride from 11c with thionyl chloride, followed by the reaction with AlCl3 did not even
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Published 08 Aug 2017

BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide

  • Ludmila Škorpilová,
  • Silvie Rimpelová,
  • Michal Jurášek,
  • Miloš Buděšínský,
  • Jana Lokajová,
  • Roman Effenberg,
  • Petr Slepička,
  • Tomáš Ruml,
  • Eva Kmoníčková,
  • Pavel B. Drašar and
  • Zdeněk Wimmer

Beilstein J. Org. Chem. 2017, 13, 1316–1324, doi:10.3762/bjoc.13.128

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  • reaction of 4-iodo-L-phenylalanine with thionyl chloride in MeOH in quantitative yield [33]. The successive acylation of the α-amino group with 5-azidovaleric acid catalyzed by T3P (propylphosphonic anhydride) in the mixture of pyridine and AcOEt gave azidoterminated product 1 in 70% yield. Alkaline
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Published 04 Jul 2017

Molecular-level architectural design using benzothiadiazole-based polymers for photovoltaic applications

  • Vinila N. Viswanathan,
  • Arun D. Rao,
  • Upendra K. Pandey,
  • Arul Varman Kesavan and
  • Praveen C. Ramamurthy

Beilstein J. Org. Chem. 2017, 13, 863–873, doi:10.3762/bjoc.13.87

Graphical Abstract
  • synthesis of monomer M1 started with the cyclization of o-phenylenediamine with thionyl chloride in the presence of triethylamine, a strong base and dichloromethane as the solvent at 0 °C. Compound 1 was then treated with bromine and HBr to obtain 4,7-dibromobenzo[c][1,2,5]thiadiazole (2). The latter
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Published 10 May 2017

Synthesis of 1-indanones with a broad range of biological activity

  • Marika Turek,
  • Dorota Szczęsna,
  • Marek Koprowski and
  • Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

Graphical Abstract
  • benzoic acids 15 with thionyl chloride, reacted with ethylene and the resulting intermediates underwent an intramolecular Friedel–Crafts alkylation to form 1-indanones 16 (Scheme 6). Both arylpropionic and 3-arylacrylic acids 17 underwent cyclization in the presence of polyphosphoric and sulfuric acids to
  • chloride with thionyl chloride, led to the formation of 1-indanone 32 which was further transformed into the desired inhibitors 33 (Scheme 12). In the synthesis of 5-hydroxy-1-indanone, Chen and Li reacted 3-chloropropionyl chloride with 2,6-dibromophenol to give 2,6-dibromophenyl 3-chloropropionate [29
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Published 09 Mar 2017

Diastereoselective anodic hetero- and homo-coupling of menthol-, 8-methylmenthol- and 8-phenylmenthol-2-alkylmalonates

  • Matthias C. Letzel,
  • Hans J. Schäfer and
  • Roland Fröhlich

Beilstein J. Org. Chem. 2017, 13, 33–42, doi:10.3762/bjoc.13.5

Graphical Abstract
  • with benzyl chloroformate (Scheme 2b). The benzyl malonates 5 and 6 are converted to the corresponding benzyl malonyl chlorides with thionyl chloride. To these at −40 °C the auxiliary menthol (1), 8-p-anisylmenthol (4) [19], 8-methylmenthol (2) [20] or 8-phenylmenthol (3) [21] was added in the presence
  • chloride (1.3 g, 10.8 mmol) were added and the mixture was refluxed for 3 h. After evaporation of the solvent and the unreacted thionyl chloride in vacuum, the remaining yellow oil was dissolved in 20 mL methylene chloride without further purification and cooled to −40 °C. Under an argon atmosphere 2.81
  • solution in the range of 5–10 °C with a coolant of −25 °C. The further work-up follows the procedure given for the hetero-coupling reaction. General procedure for the preparation of the menthol esters: To a solution of 4.3 mmol of monobenzyl malonate 5 or 6 in 20 mL dry methylene chloride 0.8 mL thionyl
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Published 05 Jan 2017

Elongated and substituted triazine-based tricarboxylic acid linkers for MOFs

  • Arne Klinkebiel,
  • Ole Beyer,
  • Barbara Malawko and
  • Ulrich Lüning

Beilstein J. Org. Chem. 2016, 12, 2267–2273, doi:10.3762/bjoc.12.219

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  • unsymmetric trimerization of the desired tribromotriazines 3. The synthesis of 4-bromo-3-nitrobenzoyl chloride (5b) was straightforward. Commercially available 4-bromobenzoic acid (8) was nitrated according to a known procedure [18]. The reaction with thionyl chloride provided then acid chloride 5b (Figure 5
  • performed with the free carboxylic acid 11 [20] or with ester 12 [21][22]. In order to generate the methoxy-substituted benzoyl chloride 5c, methoxy ester 13 was cleaved first [23] and the resulting acid 14 was reacted with thionyl chloride. All steps were known from the literature and have been carried out
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Published 27 Oct 2016

Synthesis of highly functionalized 2,2'-bipyridines by cyclocondensation of β-ketoenamides – scope and limitations

  • Paul Hommes and
  • Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2016, 12, 1170–1177, doi:10.3762/bjoc.12.112

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  • derivative 2-PyCOBt [25][26]. During an attempt to prepare β-ketoenamide 3a by in situ generation of picolinic acid chloride with thionyl chloride under heating and by amide formation of the resulting product with 2a we isolated not only the expected compound 3a but as major component the meta-chlorinated
  • (see Supporting Information File 1). The in situ generation of the acid chloride with thionyl chloride was possible without the undesired chlorination with the more electron-deficient 6-methoxycarbonyl-substituted 2-pyridine carboxylic acid delivering with 2a the desired β-ketoenamide 3g with excellent
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Published 09 Jun 2016

Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization

  • Barry M. Trost,
  • Michael C. Ryan and
  • Meera Rao

Beilstein J. Org. Chem. 2016, 12, 1136–1152, doi:10.3762/bjoc.12.110

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  • sulfinamides [48]. The application of this method to the synthesis of our chiral sulfoxide tethers is presented in Scheme 4. Tosyl protection of the primary amine of (+)-norephedrine and treatment with thionyl chloride furnishes chiral oxathiazolidine 2-oxide 7 as a single diastereomer in 87% yield over two
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Published 07 Jun 2016

Synthesis of a deuterated probe for the confocal Raman microscopy imaging of squalenoyl nanomedicines

  • Eric Buchy,
  • Branko Vukosavljevic,
  • Maike Windbergs,
  • Dunja Sobot,
  • Camille Dejean,
  • Simona Mura,
  • Patrick Couvreur and
  • Didier Desmaële

Beilstein J. Org. Chem. 2016, 12, 1127–1135, doi:10.3762/bjoc.12.109

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  • (along with N2 and the trisyl anion) which upon condensation with squalenaldehyde 10 furnished the desired allylic alcohol 16 in 59% yield. Reduction of the hydroxy group of 16 was straightforwardly achieved in 47% yield by treatment with a large excess of thionyl chloride followed by LiAlD4 reduction
  • . We next turned to the elaboration of the isopropylidene-d6 moiety. In the event, the Shapiro reaction using trisylhydrazide 14 delivered the expected allylic alcohol 21 in 70% yield. The latter afforded the deuterated ketal 22 in 52% yield, upon sequential treatment with thionyl chloride and LiAlD4
  • using the van Tamelen sequence (i. 1 equiv NBS, THF, H2O; ii. K2CO3, MeOH; iii. H3IO6, Et2O) afforded the aldehyde 26 in 16% overall yield. Uneventfully, the Shapiro reaction with trisylhydrazone 14 produced the allylic alcohol 27. Thionyl chloride treatment followed by LiAlD4 reduction delivered
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Published 06 Jun 2016

A cross-metathesis approach to novel pantothenamide derivatives

  • Jinming Guan,
  • Matthew Hachey,
  • Lekha Puri,
  • Vanessa Howieson,
  • Kevin J. Saliba and
  • Karine Auclair

Beilstein J. Org. Chem. 2016, 12, 963–968, doi:10.3762/bjoc.12.95

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  • reflux conditions (100 °C) with ethanol and thionyl chloride added in two portions separated by three hours [18]. Alternatively, it was found here that a microwave reactor reduced the overall reaction time down to 30 minutes, with an isolated yield of 90%, comparable to that of the thermal reaction
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Published 13 May 2016

Profluorescent substrates for the screening of olefin metathesis catalysts

  • Raphael Reuter and
  • Thomas R. Ward

Beilstein J. Org. Chem. 2015, 11, 1886–1892, doi:10.3762/bjoc.11.203

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  • platereader was used. N-Allyl-5-methoxynaphthalene-1-sulfonamide (12). To a DMF solution (30 mL) of sodium 5-methoxynaphthalene-1-sulfonate (11, 1.30 g, 5.00 mmol, 1.00 equiv), cooled on an ice bath, thionyl chloride (1.09 mL, 15.0 mmol, 3.00 equiv) was added dropwise. After the complete addition, the ice
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Published 12 Oct 2015

The preparation of new functionalized [2.2]paracyclophane derivatives with N-containing functional groups

  • Henning Hopf,
  • Swaminathan Vijay Narayanan and
  • Peter G. Jones

Beilstein J. Org. Chem. 2015, 11, 437–445, doi:10.3762/bjoc.11.50

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  • pseudo-para-substituted [2.2]paracyclophane derivatives carrying N-functional groups. As shown in Scheme 4, the crucial substrate 25 was prepared from the pseudo-para-dibromide 24 [24][29]. Treating 25 with thionyl chloride in DMF yielded the bis(acyl chloride) 26 in quantitative yield. In contrast to
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Published 07 Apr 2015

Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction

  • Vicky Gheerardijn,
  • Jos Van den Begin and
  • Annemieke Madder

Beilstein J. Org. Chem. 2014, 10, 2566–2572, doi:10.3762/bjoc.10.268

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  • available, we have synthesized histidine as a methyl ester (2) with thionyl chloride in methanol in good yield according to literature procedures [49]. Although basic hydrolysis of alkyl esters has been shown to imply long reaction times, side-product formation and low reaction yields [50], we found that
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Published 04 Nov 2014
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