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Search for "one-pot reaction" in Full Text gives 176 result(s) in Beilstein Journal of Organic Chemistry.

Application of heterocyclic aldehydes as components in Ugi–Smiles couplings

  • Katelynn M. Mason,
  • Michael S. Meyers,
  • Abbie M. Fox and
  • Sarah B. Luesse

Beilstein J. Org. Chem. 2016, 12, 2032–2037, doi:10.3762/bjoc.12.191

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  • Diels–Alder (US-IMDA) reaction with substituted 2-furaldehyde and allylamine (Scheme 1), which provides direct access to N-arylepoxyisoindolines 1 through a simple, one-pot reaction [23]. Through this stereoselective tandem process, six new bonds and four stereocenters are generated in one synthetic
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Published 15 Sep 2016

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

  • Forrest S. Etheridge,
  • Roshan J. Fernando,
  • Sandra Pejić,
  • Matthias Zeller and
  • Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

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  • using Zn(OAc)2 to a 2-step, one pot reaction with sodium hydride in tetrahydrofuran, followed by the addition of zinc(II) chloride. Zinc(II) and BF2+ chelates were purified by silica gel column chromatography to isolate the chelates as blue solids and the identity and purity was confirmed by NMR
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Published 29 Aug 2016

Ionic liquids as transesterification catalysts: applications for the synthesis of linear and cyclic organic carbonates

  • Maurizio Selva,
  • Alvise Perosa,
  • Sandro Guidi and
  • Lisa Cattelan

Beilstein J. Org. Chem. 2016, 12, 1911–1924, doi:10.3762/bjoc.12.181

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  • publication, Gade et al. also achieved a high selectivity toward GD in a one-pot reaction starting from glycerol and DMC [66]. Using tetramethylammonium hydroxide ([TMA][OH]) as basic catalyst, a high selectivity (78%) for GD was reached under mild operating conditions (80 °C, 90 min). The results suggested
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Published 26 Aug 2016

Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides

  • Franziska Hemmerling and
  • Frank Hahn

Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148

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  • that is produced in Streptomyces species [134][135]. The respective biosynthetic pathway has been fully reconstituted in an in vitro one-pot reaction [136]. The flavoprotein EncM transforms the C12 methylene group of the octaketidic PKS type II product 139 in a two-step oxidation sequence using the
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Published 20 Jul 2016

One-pot synthesis of tetracyclic fused imidazo[1,2-a]pyridines via a three-component reaction

  • Bo Yang,
  • Chuanye Tao,
  • Taofeng Shao,
  • Jianxian Gong and
  • Chao Che

Beilstein J. Org. Chem. 2016, 12, 1487–1492, doi:10.3762/bjoc.12.145

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  • reaction followed by a retro-aza-ene reaction and subsequent nucleophilic reaction of the in-situ generated imidazo[1,2-a]pyridines bearing an isocyanate functional group. Keywords: Groebke–Blackburn–Bienaymé reaction; imidazo[1,2-a]pyridines; multi-component reaction; one-pot reaction; Introduction
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Published 18 Jul 2016

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

  • Mohammad Haji

Beilstein J. Org. Chem. 2016, 12, 1269–1301, doi:10.3762/bjoc.12.121

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  • were resistant to this reaction. The trimethylchlorosilane-mediated one-pot reaction of diethyl (3,3,3-trifluoropropyl-2-oxo)phosphonate (8) with aryl aldehydes 9 and urea under Biginelli conditions has been presented by Timoshenko et al. (Scheme 3) [27]. The resulting 4-hydroxytetrahydropyrimidin-2
  • -aminophosphonate 26 in 99% yield (Scheme 7) [34]. The reaction of isatin (27) with diethyl phosphite and benzylamine under similar conditions gave the corresponding α-aminophosphonate 28 in 90% yield together with small amounts of α-hydroxyphosphonate 29 as a side product (Scheme 8). The one-pot reaction of
  • for the rapid access of heterocyclic phosphonates is the combination of the Kabachnik–Fields reaction with a subsequent ring closure. Thus, the one-pot reaction of 5-chloro-2-pentanone (46) with ammonia and diethyl phosphonate in ethanol lead to the non-isolable intermediate 47 which was directly
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Published 21 Jun 2016

A convenient route to symmetrically and unsymmetrically substituted 3,5-diaryl-2,4,6-trimethylpyridines via Suzuki–Miyaura cross-coupling reaction

  • Dariusz Błachut,
  • Joanna Szawkało and
  • Zbigniew Czarnocki

Beilstein J. Org. Chem. 2016, 12, 835–845, doi:10.3762/bjoc.12.82

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  • unsymmetrically substituted diarylpyridines, difficult to access by other methods. Keywords: arylpyridines; cross coupling reaction; heteroaromatics; one-pot reaction; palladium catalyst; Introduction Nitrogen heterocycles are an important class of compounds widely present in agrochemical products [1][2] and
  • monoarylated intermediate. Two alternative approaches were based on a one-pot reaction concept, which is advantageous from the point of view of costs (solvents, adsorbents etc.) and work-up procedure. Route 2 is based on the stepwise diarylation of 1 without isolation of the monoarylated product. We also
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Published 28 Apr 2016

Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

  • Guozheng Huang,
  • Simon Schramm,
  • Jörg Heilmann,
  • David Biedermann,
  • Vladimír Křen and
  • Michael Decker

Beilstein J. Org. Chem. 2016, 12, 662–669, doi:10.3762/bjoc.12.66

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  • , Prague 4, CZ-14220, Czech Republic 10.3762/bjoc.12.66 Abstract Various Mitsunobu conditions were investigated for a series of flavonolignans (silybin A, silybin B, isosilybin A, and silychristin A) to achieve either selective esterification in position C-23 or dehydration in a one-pot reaction yielding
  • pure (10R,11R)- and (10S,11S)-hydnocarpin D described to date and gives 56% yield starting from commercially available silibinin in a one-pot reaction. Evaluation of Mitsunobu conditions and reagents applied for esterification and dehydration, respectively, enabled us to exclusively obtain either the
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Published 08 Apr 2016

Iridium/N-heterocyclic carbene-catalyzed C–H borylation of arenes by diisopropylaminoborane

  • Mamoru Tobisu,
  • Takuya Igarashi and
  • Naoto Chatani

Beilstein J. Org. Chem. 2016, 12, 654–661, doi:10.3762/bjoc.12.65

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  • derivatives by treatment with protecting groups in a one-pot reaction sequence. The reactivity of 1g has previously been well-exploited in catalytic borylation of aryl halides [22][23][24][25][26][27]. Herein, we report the C–H borylation of arenes using 1g catalyzed by an Ir/N-heterocyclic carbene (NHC
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Published 07 Apr 2016

Recent advances in N-heterocyclic carbene (NHC)-catalysed benzoin reactions

  • Rajeev S. Menon,
  • Akkattu T. Biju and
  • Vijay Nair

Beilstein J. Org. Chem. 2016, 12, 444–461, doi:10.3762/bjoc.12.47

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  • catalyst rapidly shuttles the intermediate δ-keto aldehyde 61 to the final product preventing the erosion of enantioselectivity [54]. This cascade reaction constitutes a fine example of symbiotic dual-catalysis wherein both catalysts perform better together in a one-pot reaction than they do independently
  • product 81 (Scheme 45). The yields are moderate; however excellent diastereo- and enantioselectivities were observed for the one-pot reaction [62]. In a similar fashion, an asymmetric multicatalytic cascade reaction involving the dienal 82 and unsaturated cyclic sulfonylimine 83 afforded spiro-fused
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Published 09 Mar 2016

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

  • Charlotte Collet,
  • Françoise Chrétien,
  • Yves Chapleur and
  • Sandrine Lamandé-Langle

Beilstein J. Org. Chem. 2016, 12, 353–361, doi:10.3762/bjoc.12.39

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  • experimental data). The compounds myo-11 and scyllo-11 were obtained in 80% and 76% yield, respectively in a one pot reaction by the treatment of myo-1 and scyllo-1 with triphenylmethyl chloride in pyridine and a catalytic amount of DMAP at 40 °C for three days followed by the addition of acetic anhydride [46
  • chloride, followed by peracetylation with acetic anhydride in a one pot reaction [46]. Myo-18 and scyllo-18 were obtained in 74 and 70% yield, respectively. It is worthy to note that the tertiary hydroxy group in myo-18 and scyllo-18 remained unprotected under these conditions. The literature data are
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Published 25 Feb 2016

Synthesis of bi- and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: A family of valuable products by click chemistry

  • Zhan-Jiang Zheng,
  • Ding Wang,
  • Zheng Xu and
  • Li-Wen Xu

Beilstein J. Org. Chem. 2015, 11, 2557–2576, doi:10.3762/bjoc.11.276

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  • that compound 44 showed the highest activity against B. subtilis and E. coli due to the presence of a rigid pyridine nucleus. The authors further prepared various amide-linked bistriazoles by a three-component one-pot reaction of the amide-linked dialkynes, benzyl bromides and sodium azide catalyzed by
  • 1,2,3-bistriazole. The synthesis of bistriazoles via a sequential one-pot reaction. Previous reports on the copper-catalyzed Huisgen cycloaddition to bistriazoles with spacers. Previous reports on the copper-catalyzed Huisgen cycloaddition to bistriazoles with spacers. Acknowledgements This project
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Published 11 Dec 2015

Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) – precursors for dyes and drugs

  • Enas M. Malik,
  • Younis Baqi and
  • Christa E. Müller

Beilstein J. Org. Chem. 2015, 11, 2326–2333, doi:10.3762/bjoc.11.253

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  • inert solvent (e.g., nitrobenzene) to form 1-aminoanthraquinone-2-sulfonic acid (4), the salt of which is then brominated to give bromaminic acid sodium salt (2). Sulfonation of 3 (oleum method) is achieved by the use of oleum followed by bromination in a one-pot reaction. Therefore, the oleum method is
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Published 26 Nov 2015

Selected synthetic strategies to cyclophanes

  • Sambasivarao Kotha,
  • Mukesh E. Shirbhate and
  • Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

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  • accomplished in a one-pot reaction under Wolff–Kishner reaction conditions to generate 223 and 259, respectively (Scheme 41). Cycloaddition reactions [2 + 2] Cycloaddition: Roemer and Lentz [175] have reported the synthesis of fluorinated ferrocenophanes from 1,10-bis(trifluorovinyl)ferrocene and 1,4-(1,10
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Published 29 Jul 2015

Azobenzene-based inhibitors of human carbonic anhydrase II

  • Leander Simon Runtsch,
  • David Michael Barber,
  • Peter Mayer,
  • Michael Groll,
  • Dirk Trauner and
  • Johannes Broichhagen

Beilstein J. Org. Chem. 2015, 11, 1129–1135, doi:10.3762/bjoc.11.127

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  • -pot reaction over three steps in 25%. By diazotization of 1d and trapping the salt with TMS-azide, we obtained azido azobenzene 1e in 63% yield through a [3 + 2] and retro-[3 + 2] cycloaddition (Scheme 1b) according to the procedure of Barral et al [10]. For the Mills reaction, different nitroso
  • led to azobenzenes 1a [6], 1b [9] and 1c, in moderate to low yields (43%, 38% and 25%, respectively) (Scheme 1a). Employing methylene-protected aniline 2 (crystal structure depicted in Scheme 1e) according to the procedure from Supuran and co-workers [6], amino azobenzene 1d was isolated after a one
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Published 07 Jul 2015

Metal-free one-pot synthesis of 2-substituted and 2,3-disubstituted morpholines from aziridines

  • Hongnan Sun,
  • Binbin Huang,
  • Run Lin,
  • Chao Yang and
  • Wujiong Xia

Beilstein J. Org. Chem. 2015, 11, 524–529, doi:10.3762/bjoc.11.59

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  • (R)-2-phenyl-N-tosylazetidine (1o) with 2-bromoethanol and/or 3-bromopropanol under the one-pot reaction conditions, afforded the seven-membered product (S)-3o and the eight-membered compound (S)-3ob in 65% and 60% yield with 52% and 67% ee, respectively. Based on the above results, a viable
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Published 22 Apr 2015

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

  • Igor B. Krylov,
  • Vera A. Vil’ and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13

Graphical Abstract
  • [146]. The coupling reaction with N-hydroxyphthalimide (154b) was carried out using the NaI/aqueous t-BuOOH/KOH system instead of Bu4NI/t-BuOOH in decane [146]. The resulting activated esters 159 and 160 were isolated or used in the one-pot reaction with amines to prepare amides (Scheme 32). The
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Published 20 Jan 2015

Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols

  • Bianca Rossi,
  • Nadia Pastori,
  • Simona Prosperini and
  • Carlo Punta

Beilstein J. Org. Chem. 2015, 11, 66–73, doi:10.3762/bjoc.11.10

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  • reported optimized conditions for the selective free radical nucleophilic addition of ethers and alcohols to ketimines generated in situ under non-anhydrous conditions. The protocol consists of a three-component, one-pot reaction involving an aromatic amine, a ketone, and the source of the ketyl radical
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Published 15 Jan 2015

Three-component synthesis of C2F5-substituted pyrazoles from C2F5CH2NH2·HCl, NaNO2 and electron-deficient alkynes

  • Pavel K. Mykhailiuk

Beilstein J. Org. Chem. 2015, 11, 16–24, doi:10.3762/bjoc.11.3

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  • Pavel K. Mykhailiuk Enamine Ltd., Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine; and Department of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska Street, 64, Kyiv 01601, Ukraine 10.3762/bjoc.11.3 Abstract A one-pot reaction between C2F5CH2NH2·HCl, NaNO2 and electron
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Published 06 Jan 2015

Sequential decarboxylative azide–alkyne cycloaddition and dehydrogenative coupling reactions: one-pot synthesis of polycyclic fused triazoles

  • Kuppusamy Bharathimohan,
  • Thanasekaran Ponpandian,
  • A. Jafar Ahamed and
  • Nattamai Bhuvanesh

Beilstein J. Org. Chem. 2014, 10, 3031–3037, doi:10.3762/bjoc.10.321

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  • of our knowledge, until now there have been no reports describing the combination of decarboxylative CuAAC reaction and C–H activation in an one-pot fashion. This strategy describes the preparation of fused triazoles by one-pot reaction of 2-alkynoic acid and azide derivatives. Results and Discussion
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Published 17 Dec 2014

One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates

  • Joshua P. Barham,
  • Matthew P. John and
  • John A. Murphy

Beilstein J. Org. Chem. 2014, 10, 2981–2988, doi:10.3762/bjoc.10.316

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  • construct THIQs using green technologies, in mild conditions and with high atom efficiencies. Catalytic oxidative functionalisation of the C–H bond α- to the amine function is one such methodology. Iminium salts generated in this way can be intercepted by a nucleophile in a one-pot reaction (Scheme 1
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Published 12 Dec 2014

Solution processable diketopyrrolopyrrole (DPP) cored small molecules with BODIPY end groups as novel donors for organic solar cells

  • Diego Cortizo-Lacalle,
  • Calvyn T. Howells,
  • Upendra K. Pandey,
  • Joseph Cameron,
  • Neil J. Findlay,
  • Anto Regis Inigo,
  • Tell Tuttle,
  • Peter J. Skabara and
  • Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2683–2695, doi:10.3762/bjoc.10.283

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  • one-pot reaction. Extending the conjugated π-system of a compound leads to a narrower HOMO–LUMO gap and a bathochromic shift of the absorption spectrum. Both effects are usually desirable to enhance the solar absorption. Therefore, an extended analogue of compound 6 with an additional thiophene ring
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Published 18 Nov 2014

One-pot four-component reaction for convenient synthesis of functionalized 1-benzamidospiro[indoline-3,4'-pyridines]

  • Chao Wang,
  • Yan-Hong Jiang and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2014, 10, 2671–2676, doi:10.3762/bjoc.10.281

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  • ; multicomponent reaction; one-pot reaction; spiro[indoline-3,4'-pyridine]; Introduction The spirooxindole system is the core structure of many natural products and pharmaceutically important structures with notable structural complexity and biological activities of great interest [1][2][3][4]. Accordingly, many
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Published 14 Nov 2014

(CF3CO)2O/CF3SO3H-mediated synthesis of 1,3-diketones from carboxylic acids and aromatic ketones

  • JungKeun Kim,
  • Elvira Shokova,
  • Victor Tafeenko and
  • Vladimir Kovalev

Beilstein J. Org. Chem. 2014, 10, 2270–2278, doi:10.3762/bjoc.10.236

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  • recently reported by us [27] and decarboxylation was subsequently carried out, 1,3-diphenylphosphorylated acetone 5 could be obtained (reaction 2 in Scheme 2). The two-stage one-pot reaction of γ-phenylbutanoic acid (1c) and 3-hydroxy-1-adamantylacetic acid (1k) gave as a result the trifluoroacetylated
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Published 26 Sep 2014

Synthesis of phosphoramidites of isoGNA, an isomer of glycerol nucleic acid

  • Keunsoo Kim,
  • Venkateshwarlu Punna,
  • Phaneendrasai Karri and
  • Ramanarayanan Krishnamurthy

Beilstein J. Org. Chem. 2014, 10, 2131–2138, doi:10.3762/bjoc.10.220

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  • N6-benzoyladenine reaction). Initially, we tried to simultaneously deprotect both Boc groups and the TBDPS group in the presence of TBAF in a one-pot reaction [29]. However, only the TBDPS group was removed and a quantitative amount of mono-protected compound 30 was produced (Scheme 6). The fluoride
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Published 08 Sep 2014
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