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Search for "carboxylates" in Full Text gives 150 result(s) in Beilstein Journal of Organic Chemistry.

Switchable molecular tweezers: design and applications

  • Pablo Msellem,
  • Maksym Dekthiarenko,
  • Nihal Hadj Seyd and
  • Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

Graphical Abstract
  • between a cis and a trans-conformation. By the addition of an anion, the tweezers are locked in a closed form thanks to the H-bond formed with both urea moieties. The authors reported the closing of the tweezers using chiral carboxylates associated with circular dichroism (CD) response. In the presence of
  • an achiral diamine (1,12-diaminododecane or DAD) that binds to both Zn–porphyrins and sets them further apart, a higher CD signal intensity is obtained making it a sensitive probe for determining the absolute stereochemistry of chiral carboxylates directly, without the need for derivatization. More
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Published 01 Mar 2024

Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates

  • Xing Liu,
  • Wenjing Shi,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1923–1932, doi:10.3762/bjoc.19.143

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  • spiro[indoline-3,5'-[1,2]diazepine]-6'-carboxylates 5a–g in 63–77% yields (Scheme 3). The substituents on both substrates also showed little effect on the yields. The chemical structures were fully characterized by HRMS, IR, 1H and 13C NMR spectra. For demonstrating the synthetic value of this protocol
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Published 18 Dec 2023

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

  • Tinglan Liu,
  • Yu Zhou,
  • Junhong Tang and
  • Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

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  • electrophile compared to other alkyl halides, such as related bromides and chlorides. As a result, an effective iododecarboxylation provides a versatile platform for a range of decarboxylative reactions. Shang and co-workers recently found that aliphatic carboxylates and lithium iodide could undergo
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Published 22 Nov 2023

Consecutive four-component synthesis of trisubstituted 3-iodoindoles by an alkynylation–cyclization–iodination–alkylation sequence

  • Nadia Ledermann,
  • Alae-Eddine Moubsit and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2023, 19, 1379–1385, doi:10.3762/bjoc.19.99

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  • that are accessible in two steps from indole carboxylates [36]. Our two-step approach taking advantage of a de novo formation of 3-iodoindoles with variable substitution pattern in a consecutive four-component process provides a concise access to the aforementioned class of emitters. For example the
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Published 14 Sep 2023

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

  • Dmitry B. Vinogradov,
  • Alexei N. Izmest’ev,
  • Angelina N. Kravchenko,
  • Yuri A. Strelenko and
  • Galina A. Gazieva

Beilstein J. Org. Chem. 2023, 19, 1047–1054, doi:10.3762/bjoc.19.80

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  • transformations of the heterocyclic system proceeding by an ANRORC mechanism under the action of KOH in methanol. Thus, 6-oxindolylideneimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazines are transformed into substituted 2-oxoquinoline-4-carboxylates in the presence of excess KOH [20] while their 6-arylmethylidene
  • functionalized imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine derivatives into new heterocyclic systems. Alkaline hydrolysis of esters 1a,b. aDetermined by 1H NMR spectroscopy; bisolated yields. Synthesis of potassium imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazine-7-carboxylates. Plausible rearrangement
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Published 28 Jul 2023

Light-responsive rotaxane-based materials: inducing motion in the solid state

  • Adrian Saura-Sanmartin

Beilstein J. Org. Chem. 2023, 19, 873–880, doi:10.3762/bjoc.19.64

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  • , incorporating different units that allow the integration within the corresponding materials. Thus, the incorporation of coordinating groups (i.e., pyridines or carboxylates) in the molecular design will allow the integration of such rotaxanes in MOFs [70], while other substituents will be necessary to prepare
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Published 14 Jun 2023

Strategies in the synthesis of dibenzo[b,f]heteropines

  • David I. H. Maier,
  • Barend C. B. Bezuidenhoudt and
  • Charlene Marais

Beilstein J. Org. Chem. 2023, 19, 700–718, doi:10.3762/bjoc.19.51

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  • the enol carboxylate and subsequent 1,2 radical rearrangement and decarboxylation. Moderate to good yields of dibenzo[b,f]oxepine carboxylates 25 were achieved (63–85%). Stopka et al. [46] reported on tandem C–H functionalisation and ring expansion as an alternative to the Wagner–Meerwin rearrangement
  • . Among these, Heck reaction conditions allowed for the coupling of aryl acrylates 50 to aryl halides 48 and 49, followed by intramolecular Pd-catalysed amination or etherification to give C-10 carboxylates of dibenzo[b,f]azepine 55 and dibenz[b,f]oxepine 54 in good yield (Scheme 11). However, no ring
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Published 22 May 2023

Synthesis of medium and large phostams, phostones, and phostines

  • Jiaxi Xu

Beilstein J. Org. Chem. 2023, 19, 687–699, doi:10.3762/bjoc.19.50

Graphical Abstract
  • '-carboxylates 83 in 5–10% yield as byproducts. The major products 84 were generated via Michael addition and the nucleophilic addition–elimination of the carbanion of the generated enolate moiety, while the oxyanion of the enolate moiety attacked the phosphorus to form the byproducts 83 (Scheme 18) [40][41
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Published 15 May 2023

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

  • Austin Pounder,
  • Eric Neufeld,
  • Peter Myler and
  • William Tam

Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38

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Published 24 Apr 2023

Combining the best of both worlds: radical-based divergent total synthesis

  • Kyriaki Gennaiou,
  • Antonios Kelesidis,
  • Maria Kourgiantaki and
  • Alexandros L. Zografos

Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1

Graphical Abstract
  • allylation using achiral H-PHOX followed to produce 16, without being isolated. From this point of divergence, Baran’s group managed to reveal the requisite phthalimide carboxylates for each precursor of the diverse natural products and transformed it carrying out Giese reactions or nickel-catalyzed radical
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Published 02 Jan 2023

Computational model predicts protein binding sites of a luminescent ligand equipped with guanidiniocarbonyl-pyrrole groups

  • Neda Rafieiolhosseini,
  • Matthias Killa,
  • Thorben Neumann,
  • Niklas Tötsch,
  • Jean-Noël Grad,
  • Alexander Höing,
  • Thies Dirksmeyer,
  • Jochen Niemeyer,
  • Christian Ottmann,
  • Shirley K. Knauer,
  • Michael Giese,
  • Jens Voskuhl and
  • Daniel Hoffmann

Beilstein J. Org. Chem. 2022, 18, 1322–1331, doi:10.3762/bjoc.18.137

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  • to efficiently bind to oxo-anions such as carboxylates [10]. These compounds were already used to specifically address carboxylates on the surface of proteins. Many artificial receptors based on guanidinium scaffolds use hydrogen bonding, charge pairing, and hydrophobic interactions to complex oxo
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Published 23 Sep 2022

Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates

  • Péter Kisszékelyi,
  • Tibor Peňaška,
  • Klára Stankovianska,
  • Mária Mečiarová and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2022, 18, 1195–1202, doi:10.3762/bjoc.18.124

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  • -3(4H)-ones were also prepared by cyclization of 1,2-diaryldisulfanes with dialkyl but-2-ynedioates [24][25]. N-Substituted benzo-1,4-thiazine-2-carboxylates 4 (Figure 1) were prepared by m-CPBA-mediated oxidative ring expansion of substituted benzothiazoles [26], or via copper-catalyzed
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Published 09 Sep 2022

Electrogenerated base-promoted cyclopropanation using alkyl 2-chloroacetates

  • Kouichi Matsumoto,
  • Yuta Hayashi,
  • Kengo Hamasaki,
  • Mizuki Matsuse,
  • Hiyono Suzuki,
  • Keiji Nishiwaki and
  • Norihito Kawashita

Beilstein J. Org. Chem. 2022, 18, 1116–1122, doi:10.3762/bjoc.18.114

Graphical Abstract
  • seems to be the trialkyl propane-1,2,3-carboxylates [32], because the HRMS analyses of the isolated compounds, such as 6 (Table 3, entry 2), 10 (Table 3, entry 5), and 12 (Table 3, entry 6), which were not of high purity, showed the existence of the corresponding trialkyl propane-1,2,3-carboxylates
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Published 29 Aug 2022

An isoxazole strategy for the synthesis of 4-oxo-1,4-dihydropyridine-3-carboxylates

  • Timur O. Zanakhov,
  • Ekaterina E. Galenko,
  • Mikhail S. Novikov and
  • Alexander F. Khlebnikov

Beilstein J. Org. Chem. 2022, 18, 738–745, doi:10.3762/bjoc.18.74

Graphical Abstract
  • -aryl-, 2-aryl-6-aryl and 2,6-diaryl-5-aryl/hetaryl-substituted methyl 4-oxo-1,4-dihydropyridine-3-carboxylates by Mo(CO)6-mediated ring expansion of methyl 2-(isoxazol-5-yl)-3-oxopropanoates. The high reactivity of 4-oxo-1,4-dihydropyridine-3-carboxylates synthesized provide easy access to 2,4,6
  • , contain the fragment of 4-oxo-1,4-dihydropyridine-3-carboxamide [5][6][7]. Finding new synthetic methods for the preparation of derivatives of 4-oxo-1,4-dihydropyridine-3-carboxylic acid are therefore relevant. Some alkyl 6-aryl-2-methyl-4-oxo-1,4-dihydropyridine-3-carboxylates were prepared by refluxing
  • rearrangement of methyl 2-(isoxazol-5-yl)-3-oxopropanoates 1. High yield transformations of compound 2 provide easy access to 2,4,6-triaryl-substituted and 1,2,5,6-tetrasubstituted nicotinates. Approaches to the synthesis of alkyl 4-oxo-1,4-dihydropyridine-3-carboxylates. Synthesis of 4-oxo-1,4-dihydropyridine
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Published 23 Jun 2022

Synthesis of 5-unsubstituted dihydropyrimidinone-4-carboxylates from deep eutectic mixtures

  • Sangram Gore,
  • Sundarababu Baskaran and
  • Burkhard König

Beilstein J. Org. Chem. 2022, 18, 331–336, doi:10.3762/bjoc.18.37

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Published 22 Mar 2022

Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks

  • Jolita Bruzgulienė,
  • Greta Račkauskienė,
  • Aurimas Bieliauskas,
  • Vaida Milišiūnaitė,
  • Miglė Dagilienė,
  • Gita Matulevičiūtė,
  • Vytas Martynaitis,
  • Sonata Krikštolaitytė,
  • Frank A. Sløk and
  • Algirdas Šačkus

Beilstein J. Org. Chem. 2022, 18, 102–109, doi:10.3762/bjoc.18.11

Graphical Abstract
  • blocks was developed. Regioisomeric methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates were prepared by the reaction of β-enamino ketoesters (including azetidine, pyrrolidine or piperidine enamines) with hydroxylamine hydrochloride. Unambiguous structural assignments were based on chiral HPLC
  • -oxazoles [34][35]. This study aimed to develop and synthesize methyl 5-(cycloaminyl)-1,2-oxazole-4-carboxylates, as new amino acid-like building blocks. This type of functionalized heterocycles could exhibit not only useful biological properties, but also find application as building blocks for the
  • signals C-3 (1JC3-N2 = 4.55 Hz), C-4 (2JC4-N2 = 1.30 Hz), and C-5 (2JC5-N2 = 1.96 Hz), which unambiguously indicates the presence of a 1,2-oxazole ring in the target compound. Also, chiral methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates 4b–g were obtained from β-enamino ketoesters 3b–g with
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Published 12 Jan 2022

Silica gel and microwave-promoted synthesis of dihydropyrrolizines and tetrahydroindolizines from enaminones

  • Robin Klintworth,
  • Garreth L. Morgans,
  • Stefania M. Scalzullo,
  • Charles B. de Koning,
  • Willem A. L. van Otterlo and
  • Joseph P. Michael

Beilstein J. Org. Chem. 2021, 17, 2543–2552, doi:10.3762/bjoc.17.170

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  • , underwent cyclization in the presence of silica gel to give ethyl 6-(hetero)aryl-2,3-dihydro-1H-pyrrolizine-5-carboxylates within minutes upon microwave heating in xylene at 150 °C. Instead of functioning as a nucleophile, the enaminone acted as an electrophile at its carbonyl group during the cyclization
  • . Yields of the bicyclic products were generally above 75%. The analogous microwave-assisted reaction to produce ethyl 2-aryl-5,6,7,8-tetrahydroindolizine-3-carboxylates from (E)-ethyl 2-[2-(2-oxo-2-arylethylidene)piperidin-1-yl]acetates failed in nonpolar solvents, but occurred in ethanol at lower
  • , was reported as recently as 2018 [55]. More interestingly, conventional heating in acetic acid of an enaminone bearing a phenacylsulfanyl substituent adjacent to nitrogen on the C=C bond produced ethyl pyrrolo[2,1-b]thiazole-5-carboxylates in moderate yield, while the corresponding microwave-assisted
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Published 13 Oct 2021

Visible-light-mediated copper photocatalysis for organic syntheses

  • Yajing Zhang,
  • Qian Wang,
  • Zongsheng Yan,
  • Donglai Ma and
  • Yuguang Zheng

Beilstein J. Org. Chem. 2021, 17, 2520–2542, doi:10.3762/bjoc.17.169

Graphical Abstract
  • )–O cross-coupling using oxime esters and phenols 76 (Scheme 30). In 2020, Loh and co-workers [104] reported the copper-catalyzed highly site-selective alkylation of heteroarene N-oxides in the presence of hypervalent iodineIII carboxylates. As an alkylating agent, the hypervalent iodineIII
  • carboxylates were reduced by active copperI complexes and produced an alkyl radical, which was then captured by a copperIII active species. Finally, after reductive elimination, the target products were obtained (Scheme 31). Conclusion This review highlighted the special features and applications of
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Published 12 Oct 2021

Facile and innovative catalytic protocol for intramolecular Friedel–Crafts cyclization of Morita–Baylis–Hillman adducts: Synergistic combination of chiral (salen)chromium(III)/BF3·OEt2 catalysis

  • Karthikeyan Soundararajan,
  • Helen Ratna Monica Jeyarajan,
  • Raju Subimol Kamarajapurathu and
  • Karthik Krishna Kumar Ayyanoth

Beilstein J. Org. Chem. 2021, 17, 2186–2193, doi:10.3762/bjoc.17.140

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  • -carboxylates [9], indenes [10][11][12][13] and indanones [14]. However, most of the reported Friedel–Crafts reactions utilize either strong Lewis acid catalysts or severe reaction conditions resulting in low yield, unwanted byproducts and tedious workup methodologies [15][16]. Therefore, developing an
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Published 26 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

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Published 30 Jul 2021

Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate

  • Eleni Dimitriou and
  • Gavin J. Miller

Beilstein J. Org. Chem. 2021, 17, 1527–1532, doi:10.3762/bjoc.17.110

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  • properties from the charged carboxylate groups within its polyuronic acid backbone. The design and inclusion of isosteric replacements for these carboxylates would underpin provision of new oligo-/polysaccharide materials with alternate physicochemical properties. Presented herein is our synthesis of
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Published 05 Jul 2021

Recent advances in palladium-catalysed asymmetric 1,4–additions of arylboronic acids to conjugated enones and chromones

  • Jan Bartáček,
  • Jan Svoboda,
  • Martin Kocúrik,
  • Jaroslav Pochobradský,
  • Alexander Čegan,
  • Miloš Sedlák and
  • Jiří Váňa

Beilstein J. Org. Chem. 2021, 17, 1048–1085, doi:10.3762/bjoc.17.84

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  • -dihydropyridine-1(2H)-carboxylates were excellent in terms of both conversion (72–96%) and enantioselectivities (87–99% ee; Table 15) [45]. In addition, the authors proposed a catalytic cycle for this reaction (Scheme 9). In 2013, the most recent NHC-Pd based system has been developed by Mullick et al. who used
  • [44][45]. Addition reaction of arylboronic acids to different enones catalysed by Pd-NHC complexes PdL7a–c [44][45]. Addition reaction of arylboronic acids to various 4-oxo-3,4-dihydropyridine-1(2H)-carboxylates catalysed by Pd-NHC complexes PdL7a–c [45]. Addition reactions of boronic acids to five
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Published 10 May 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

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  • necessary, and the resistance of the reaction was also verified from various pharmacophores to be acceptable. Conclusion In conclusion, the trifluoromethylation of methyl carboxylates to trifluoromethyl ketones is accomplished under basic conditions with fluoroform in triglyme at −40 °C. An equivalent
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Published 12 Feb 2021

Selected peptide-based fluorescent probes for biological applications

  • Debabrata Maity

Beilstein J. Org. Chem. 2020, 16, 2971–2982, doi:10.3762/bjoc.16.247

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  • serum albumin. Other biomolecules such as adenosine, adenosine monophosphate, adenosine triphosphate, phosphate, pyrophosphate, glucose, heparin, hyaluronic acid and chondroitin sulfate, and amino acids containing two carboxylates (glutamic acid and aspartic acid) have not increased the fluorescence
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Published 03 Dec 2020

UV resonance Raman spectroscopy of the supramolecular ligand guanidiniocarbonyl indole (GCI) with 244 nm laser excitation

  • Tim Holtum,
  • Vikas Kumar,
  • Daniel Sebena,
  • Jens Voskuhl and
  • Sebastian Schlücker

Beilstein J. Org. Chem. 2020, 16, 2911–2919, doi:10.3762/bjoc.16.240

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  • autofluorescence of the peptide or protein. Here, we demonstrate the use of UVRR spectroscopy with 244 nm laser excitation for the characterization of GCP as well as guanidiniocarbonyl indole (GCI), a next generation supramolecular ligand for the recognition of carboxylates. For demonstrating the feasibility of
  • (CBS) [6][7][8][9]. The GCP takes part selectively and efficiently in the complexation of carboxylates based on the electrostatic interaction between the positively charged CBS and the negatively charged carboxylate in the combination with hydrogen bonding, enabling molecular recognition even in the
  • presence of polar solvents like water. This makes GCPs promising binding partners for acidic residues such as carboxylates at the C-terminus of peptides and proteins. The intermolecular interactions upon recognition induce subtle changes in the molecular properties such as the electronic structure and bond
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Published 27 Nov 2020
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