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Search for "dicarboxylates" in Full Text gives 31 result(s) in Beilstein Journal of Organic Chemistry.

Salen–scandium(III) complex-catalyzed asymmetric (3 + 2) annulation of aziridines and aldehydes

  • Linqiang Wang and
  • Jiaxi Xu

Beilstein J. Org. Chem. 2025, 21, 1087–1094, doi:10.3762/bjoc.21.86

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  • moieties of biologically active compounds. A salen–scandium triflate complex-catalyzed asymmetric (3 + 2) annulation of dialkyl 1-sulfonylaziridine-2,2-dicarboxylates and aldehydes generated optically active functionalized oxazolidine derivatives in moderate to good yields and good to excellent
  • alcohols and aldehydes [11] and through [2 + 3] cycloaddition of azomethine ylides and carbonyl dipolarophiles [12]. Recently, the [2 + 3] annulation of aldehydes and donor–acceptor dialkyl 2-aryl-1-sulfonylaziridine-2,2-dicarboxylates, which generate azomethine ylides, has been developed for the synthesis
  • require dineopentyl aziridine-2,2-dicarboxylates to realize high enantioselectivity, while the synthesis of the chiral ligand N,N'-dioxide requires multiple steps. Herein, we present a convenient highly diastereo- and enantioselective synthesis of dialkyl 2,5-diaryl-1-sulfonyloxazolidine-2,2
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Published 28 May 2025

Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion–π interactions

  • Wen-Hui Mi,
  • Teng-Yu Huang,
  • Xu-Dong Wang,
  • Yu-Fei Ao,
  • Qi-Qiang Wang and
  • De-Xian Wang

Beilstein J. Org. Chem. 2025, 21, 884–889, doi:10.3762/bjoc.21.72

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  • Sciences, Beijing 100049, China 10.3762/bjoc.21.72 Abstract The efficient binding of dicarboxylates represents an important yet challenging issue in supramolecular chemistry. In this study, we designed functional ultracycles as hosts to accommodate large organic dicarboxylate anions. These ultracycles
  • were synthesized via a one-pot strategy starting from macrocyclic precursors. Host–dicarboxylate binding was investigated using 1H NMR titrations, revealing that B4aH exhibits strong binding affinities toward a series of dicarboxylates, with association constants reaching up to 6896 M−1. The
  • selectivity for heptanedioate (C72−) was attributed to cooperative hydrogen bonding, anion–π interactions, and a size-matching effect, as supported by DFT optimizations. Keywords: anion–π interactions; anion recognition; hydrogen bonding; dicarboxylates; ultracycles; Introduction Macrocycles containing more
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Published 06 May 2025

Hypervalent iodine-mediated intramolecular alkene halocyclisation

  • Charu Bansal,
  • Oliver Ruggles,
  • Albert C. Rowett and
  • Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 3113–3133, doi:10.3762/bjoc.20.258

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  • reductive ligand coupling (RLC) pathway would be suppressed due to reduced fluxionality of the carboxylate ligand on I(III). These important findings are expected to enhance the use of aryl iodane(III)-dicarboxylates for constructing fluorinated azaheterocycles with improved selectivity and control. Oxygen
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Published 28 Nov 2024

Tailored charge-neutral self-assembled L2Zn2 container for taming oxalate

  • David Ocklenburg and
  • David Van Craen

Beilstein J. Org. Chem. 2024, 20, 3007–3015, doi:10.3762/bjoc.20.250

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  • selectively over other dicarboxylates by maintaining the receptor stability. This study highlights the importance of a highly modular receptor design so that tailored hosts can be designed to tackle the recognition of challenging competitive analytes. Keywords: anion recognition; charge-neutral host
  • dicarboxylate receptor by binding these dianions in a coordinative fashion between the zinc centers with binding constants up to log K = 8.16 [74]. However, even this very potent host was struggling with shorter dicarboxylates and with oxalate especially, resulting in an unknown mixture of species. In general
  • of the analytes (Table 1, and Figures S27–S30 in Supporting Information File 1). Binding constants for these dicarboxylates were not determined due to the lack of clarity regarding the underlying binding equilibria and the exact speciation. It seems like the receptor does not provide a suitable size
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Published 18 Nov 2024

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

  • Ignaz Betcke,
  • Alissa C. Götzinger,
  • Maryna M. Kornet and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

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  • . An advantage of this method for preparing 1,3,5-substituted pyrazoles is its tolerance towards a wide range of substituents. Trimethyl phosphite can be added to acetylene dicarboxylates 95 to generate a zwitterion that readily reacts with electrophiles. This zwitterion undergoes a rearrangement
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Published 16 Aug 2024

(Bio)isosteres of ortho- and meta-substituted benzenes

  • H. Erik Diepers and
  • Johannes C. L. Walker

Beilstein J. Org. Chem. 2024, 20, 859–890, doi:10.3762/bjoc.20.78

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  • nitrogen-substituted 1,5-BCHeps 141a–d through a photoredox-catalysed aminoalkylation with amines 140 and iodonium dicarboxylates 139 (Scheme 15A) [27]. Both Anderson and Uchiyama also reported the synthesis of chalcogen- and tin-substituted 1,5-BCHeps 145a–f from [3.1.1]propellane (Scheme 15B) [27][47][60
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Published 19 Apr 2024

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

  • Fatemeh Doraghi,
  • Seyedeh Pegah Aledavoud,
  • Mehdi Ghanbarlou,
  • Bagher Larijani and
  • Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

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  • sulfenylation of 2‑alkyn-1-one O‑methyloximes. Lewis acid-promoted 2-substituted cyclopropane 1,1-dicarboxylates with sulfonamides and N-(arylthio)succinimides. Lewis acid-mediated cyclization of β,γ-unsaturated oximes and hydrazones with N-(arylthio/seleno)succinimides. Credible pathway for Lewis acid-mediated
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Published 27 Sep 2023

The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

  • Xiu-Yu Chen,
  • Hui Zheng,
  • Ying Han,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 982–990, doi:10.3762/bjoc.19.73

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  • acetylenedicarboxylate and 5,6-unsubstituted 1,4-dihydropyridines with N–Ar groups did not give the above isoquinolino[1,2-f][1,6]naphthyridines, but the unique 2-azabicyclo[4.2.0]octa-3,7-diene-7,8-dicarboxylates were isolated in moderate yields. These products were obviously produced from the formal [2 + 2
  • -tetrahydrocyclopenta[b]pyrrole derivatives 6, it was found that the 1,4-dihydropyridinyl ring of the substrate was converted to a fused pyrrole ring, which might be a result from a rearrangement process of the formed 2-azabicyclo[4.2.0]octa-3,7-diene-7,8-dicarboxylates 5a–o at elevated temperature. The chemical
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Published 29 Jun 2023

Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates

  • Hui Zheng,
  • Ying Han,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 991–998, doi:10.3762/bjoc.18.99

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  • at room temperature resulted in 3,3-dicyano-5-hydroxy-5-arylcyclopent-1-ene-1,2-dicarboxylates in high yields. More importantly, the DABCO-promoted domino reaction of two molecules of each phenacylmalononitrile and dialkyl but-2-ynedioate in acetonitrile at room temperature afforded unique
  • base-promoted reactions between phenacylmalononitriles and dialkyl but-2-ynedioates. Here we wish to report the selective synthesis of cyclopent-1-ene-1,2-dicarboxylates and complex carboxamide-bridged dicyclopentene derivatives in good yields and with high diastereoselectivity (reaction 5 in Scheme 1
  • reaction of phenacyl bromide, malononitrile, dialkyl but-2-ynedioate, and triphenylphosphine has been already reported, in which diethyl 3-phenyl-5,5-dicyanocyclopent-2-ene-1,2-dicarboxylates were produced by further elimination of a hydroxy group [30]. In the present reaction, the hydroxy group is still
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Published 08 Aug 2022

Recent advances in the syntheses of anthracene derivatives

  • Giovanni S. Baviera and
  • Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

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  • corresponding [n+2]acene-2,3-diethyl diesters 95 by the procedure described above. The scope of the reaction included five examples of substituted anthracene-2,3-dicarboxylates bearing Cl or alkoxy groups (43–86% yield). Lin et al. also applied the same approach to synthesize acene-2,3-dinitriles 96 by using
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Published 10 Aug 2021

Optical detection of di- and triphosphate anions with mixed monolayer-protected gold nanoparticles containing zinc(II)–dipicolylamine complexes

  • Lena Reinke,
  • Julia Bartl,
  • Marcus Koch and
  • Stefan Kubik

Beilstein J. Org. Chem. 2020, 16, 2687–2700, doi:10.3762/bjoc.16.219

Graphical Abstract
  • , which should give rise to optical probes for dicarboxylates or peptides [46][47][48]. Schematic illustration of the analyte-induced crosslinking of gold nanoparticles containing a mixture of ligands of which one contains a peripheral zinc(II)–dipicolylamine unit while the other one mainly serves to
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Published 02 Nov 2020

An overview on disulfide-catalyzed and -cocatalyzed photoreactions

  • Yeersen Patehebieke

Beilstein J. Org. Chem. 2020, 16, 1418–1435, doi:10.3762/bjoc.16.118

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  • olefins, this method could not give satisfactory results. In order to overcome this weakness, the authors also developed disulfide-catalyzed [3 + 2] methylenecyclopentane annulations of unactivated alkenes with methylenecyclopropanecarboxylates and -dicarboxylates 11 (Scheme 4b) [11]. This annulation
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Published 23 Jun 2020

Recent synthesis of thietanes

  • Jiaxi Xu

Beilstein J. Org. Chem. 2020, 16, 1357–1410, doi:10.3762/bjoc.16.116

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  • chloromethylthiirane (epithiochlorohydrin, 398a), with hard and weak nucleophiles [105][106][107][108][109], including phenoxides [105], carboxylates and dicarboxylates [106][107], potassium cyanide, sodium azide, hydroxylamine, trifluoromethanesulfonamide, and pyridine [108]. However, the method could only applied to
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Published 22 Jun 2020

Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes

  • Grzegorz Mlostoń,
  • Mateusz Kowalczyk,
  • André U. Augustin,
  • Peter G. Jones and
  • Daniel B. Werz

Beilstein J. Org. Chem. 2020, 16, 1288–1295, doi:10.3762/bjoc.16.109

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  • -arylcyclopropane dicarboxylates reacted with the corresponding aryl ferrocenyl thioketones in a completely diastereoselective manner to form single products in which (C-2)-Ar and (C-5)-ferrocenyl groups were oriented in a cis-fashion. In contrast, the same cyclopropanes underwent reaction with alkyl ferrocenyl
  • cyclopropanes 5, aimed at the synthesis of hitherto unreported, ferrocenyl-substituted tetrahydrothiophene dicarboxylates (thiolanes) of type 9. Results and Discussion In analogy to experiments described in our earlier publication [9], the test reaction was performed with dimethyl 2-phenylcyclopropane
  • . Formal [3 + 2]-cycloadditions of dimethyl 2-substituted cyclopropane-1,1-dicarboxylates 5a–g with ferrocenyl thioketones 8a–g, leading to dimethyl tetrahydrothiophene 3,3-dicarboxylates 9a–n (Table 1). Plausible mechanism for the formal [3 + 2]-cycloadditions of ferrocenyl thioketones 8 with D–A
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Published 10 Jun 2020

Thermal stability of N-heterocycle-stabilized iodanes – a systematic investigation

  • Andreas Boelke,
  • Yulia A. Vlasenko,
  • Mekhman S. Yusubov,
  • Boris J. Nachtsheim and
  • Pavel S. Postnikov

Beilstein J. Org. Chem. 2019, 15, 2311–2318, doi:10.3762/bjoc.15.223

Graphical Abstract
  • )cyclic iodanes. Albeit aryl-λ3-iodanes are viewed as safe and stable under ambient temperatures, systematic thermal degradation studies of hypervalent iodine reagents are still rare. In 1992 Varvoglis and co-workers investigated the thermal degradation of a variety of aryl iodine(III) dicarboxylates into
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Published 27 Sep 2019

[3 + 2]-Cycloaddition reaction of sydnones with alkynes

  • Veronika Hladíková,
  • Jiří Váňa and
  • Jiří Hanusek

Beilstein J. Org. Chem. 2018, 14, 1317–1348, doi:10.3762/bjoc.14.113

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  • supercritical carbon dioxide [41] in which 65 and 83% yields of dimethyl (or diethyl) 1-phenylpyrazole-3,4-dicarboxylates were achieved. Only in two cases involving 3-(2,4,6-trisubstituted phenyl)-4-iodosydnones (R1: 2-Br-4,6-diMe-Ph, 2,4-diBr-6-Me-Ph; R2: I) and DMAD (or its diethyl analogue) did the
  • (Scheme 3). It was also observed, that formation of isomeric pyrazole-4,5-dicarboxylates (B) can sometimes accompany the production of pyrazole-3,4-dicarboxylates (A) under thermal conditions [33] although their formation is not photoinduced (cf. next chapter) because the reaction also takes place in the
  • ], Gotthardt and Reiter [63][64] and Märky, Hansen and Schmid [65] found that irradiation of a mixture of 3-phenylsydnone or 3,4-diphenylsydnones together with DMAD gave different isomeric [3 + 2]-cycloadducts (pyrazole-4,5-dicarboxylates) than what were obtained under thermal conditions and proved the
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Published 05 Jun 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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  • University of Technology, Radvilėnų pl. 19, LT-50254 Kaunas, Lithuania Institute of Synthetic Chemistry, Kaunas University of Technology, K. Baršausko g. 59, LT-51423, Kaunas, Lithuania 10.3762/bjoc.14.110 Abstract Dialkyl 5,5'-dioxo-4,4'-bipyrazole-4,4'-dicarboxylates are readily obtained by the reaction
  • '-dioxo-4,4'-bipyrazole-4,4'-dicarboxylates of type 3. Signal of the OCH2 ester protons of reaction product 3a (500 MHz, CDCl3). ORTEP-plot of the crystal structure of compound 3a drawn with 50% displacement ellipsoids [(4S,4'S)-3a enantiomer is shown only]. The length of the C4–C4' bond connecting the
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Published 04 Jun 2018

Dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studies

  • Grzegorz Mlostoń and
  • Heinz Heimgartner

Beilstein J. Org. Chem. 2017, 13, 2235–2251, doi:10.3762/bjoc.13.221

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  • experimental results were rationalized by a computational study performed at the DFT B3LYP/6-31G(d) level of theory with the PCM solvation model [39]. The thermal [3 + 2]-cycloadditions of azomethine ylides derived from diethyl cis- and trans-1-(4-methoxyphenyl)aziridine-2,3-dicarboxylates with E-1b led to
  • -oriented ester group. The only products obtained are 1,2-dihydropyrazole-3-carboxylates 62 in good yield. Interestingly, reactions with arylhydrazines afforded, in the presence of ammonium or sodium acetate, 5-aminopyrazole-3,4-dicarboxylates 63 [64] (Scheme 20). Apparently, in these cases, the
  • be E-configured to enable cyclization with the CN group. An analogous reaction pathway was also described for the formation of 5-amino-1-carbamoylpyrazole-3,4-dicarboxylates from dialkyl dicyanofumarates E-1 and semicarbazide hydrochloride in boiling ethanol solution in the presence of sodium acetate
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Published 24 Oct 2017

Rearrangements of organic peroxides and related processes

  • Ivan A. Yaremenko,
  • Vera A. Vil’,
  • Dmitry V. Demchuk and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

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Published 03 Aug 2016

Tandem processes promoted by a hydrogen shift in 6-arylfulvenes bearing acetalic units at ortho position: a combined experimental and computational study

  • Mateo Alajarin,
  • Marta Marin-Luna,
  • Pilar Sanchez-Andrada and
  • Angel Vidal

Beilstein J. Org. Chem. 2016, 12, 260–270, doi:10.3762/bjoc.12.28

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  • that ortho-(1,3-dioxolan-2-yl)benzylidenemalonates 1 undergo tandem hydride shift/cyclization sequences leading to the corresponding indan-1-one-2,2-dicarboxylates 2. Remarkably, the first step of these processes consists of an uncommon [1,4]-hydride shift of the acetalic H atom following the
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Published 11 Feb 2016

Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates

  • Michael Edmunds,
  • Mohammed Abdul Raheem,
  • Rebecca Boutin,
  • Katrina Tait and
  • William Tam

Beilstein J. Org. Chem. 2016, 12, 239–244, doi:10.3762/bjoc.12.25

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Published 09 Feb 2016

Biocatalysis for the application of CO2 as a chemical feedstock

  • Apostolos Alissandratos and
  • Christopher J. Easton

Beilstein J. Org. Chem. 2015, 11, 2370–2387, doi:10.3762/bjoc.11.259

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  • (e.g., the TCA cycle) are replenished. These enzymes also represent interesting targets for use in CO2 transforming processes, particularly when involved in the production of TCA cycle dicarboxylates that constitute target platform chemicals, as in the cases of pyruvate carboxylase and PEPC. Enzymes
  • marinus, which folded with the aid of E. coli protein chaperones (GroEL/GroES) [83]. This resulted in catalysis of CO2 fixation and increase of carbon flux towards the ethanol product and away from glycerol, a major fermentation byproduct (Figure 3). Synthesis of dicarboxylates through pyruvate
  • carboxylation Enzymatic carboxylation of a pyruvate backbone offers an avenue to dicarboxylates, which are important biotechnological targets, through the use of CO2 as feedstock. As seen, this may be carried out by pyruvate carboxylase or PEPC which acts on phosphoenolpyruvate (19). Purified PEPC has been used
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Published 01 Dec 2015

Dicarboxylic esters: Useful tools for the biocatalyzed synthesis of hybrid compounds and polymers

  • Ivan Bassanini,
  • Karl Hult and
  • Sergio Riva

Beilstein J. Org. Chem. 2015, 11, 1583–1595, doi:10.3762/bjoc.11.174

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  • hydroxy groups by the action of an activated ester in the presence of a suitable hydrolase in organic solvents [22][23]. Different authors have shown that activated dicarboxylates are also accepted as acyl donors by these enzymes. As an example, Figure 1 shows the products obtained using divinyl adipate
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Published 09 Sep 2015

Surprisingly facile CO2 insertion into cobalt alkoxide bonds: A theoretical investigation

  • Willem K. Offermans,
  • Claudia Bizzarri,
  • Walter Leitner and
  • Thomas E. Müller

Beilstein J. Org. Chem. 2015, 11, 1340–1351, doi:10.3762/bjoc.11.144

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  • explored in several studies. Rieger et al. studied the mechanisms of the copolymerisation by homogeneous chromium(III)– and aluminium(III)–salen complexes and by heterogeneous zinc-dicarboxylates [30][31]. Experimental work on the chromium(III)– and aluminium(III)–salen complexes was combined with a
  • feasible. In mechanistic studies on zinc dicarboxylates and their application in the heterogeneously catalysed copolymerisation of CO2 and epoxides a bimetallic mechanism was proposed [31]. As post-modification of the prepared catalysts with water proved to be important for the activity of the catalysts
  • alternating polycarbonates, polyethercarbonates or cyclic carbonates. Epoxide and CO2 copolymerisation by homogeneous Cr(III)– and Al(III)–salen complexes. Heterogeneous zinc dicarboxylates for the copolymerisation of CO2 and epoxides. (* = End group of polymer chain). Backbiting mechanism for the formation
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Published 31 Jul 2015

Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles

  • Grzegorz Mlostoń,
  • Paulina Grzelak,
  • Maciej Mikina,
  • Anthony Linden and
  • Heinz Heimgartner

Beilstein J. Org. Chem. 2015, 11, 576–582, doi:10.3762/bjoc.11.63

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  • rearranged products (Pummerer-type rearrangement) upon treatment of 1H-2-benzothiopyran-3,4-dicarboxylates of type 4 with an equimolar amount of mCPBA. Conclusion The present study shows that hetaryl thioketones react with activated acetylenecarboxylates in a hetero-Diels–Alder reaction followed by the 1,3
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Published 28 Apr 2015
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