Search results

Search for "pyridine" in Full Text gives 865 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

(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

Graphical Abstract
  • catalytic system of B2cat2 and 4-phenylpyridine to form pyridine-boryl radicals which initiated ring expansion. The method was shown to be similarly tolerable of functional groups as Procter’s synthesis. Intramolecular crossed [2 + 2] cycloadditions offer an alternative approach to 1,2-disubstituted BCHs
  • -substituted endo-1,5-BCHs (±)-57a–e. Substrate modification was also possible, with oxidative transformation of a bridgehead furan leading to 1,5-BCH acid (±)-60 and pyridine reduction to secondary amine (±)-61 (Scheme 5B) [42]. Furthermore, 1,5-BCH (±)-64 was synthesised as a bioisostere of the fungicide
  • the synthesis of polysubstituted BCHeps bearing a wide range of different substitution patterns. Their synthesis utilises boronyl radicals generated from diboron compounds by a pyridine cocatalyst to induce the [2σ + 2σ] cycloaddition of cyclopropanes and bicyclobutanes [87]. Similarly densely
PDF
Album
Review
Published 19 Apr 2024

Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions

  • Martyn Jevric,
  • Julian Klepp,
  • Johannes Puschnig,
  • Oscar Lamb,
  • Christopher J. Sumby and
  • Ben W. Greatrex

Beilstein J. Org. Chem. 2024, 20, 823–829, doi:10.3762/bjoc.20.74

Graphical Abstract
  • 10.3762/bjoc.20.74 Abstract A skeletal rearrangement of a series of 6,8-dioxabicyclo[3.2.1]octan-4-ols has been developed using SOCl2 in the presence of pyridine. An oxygen migration from C5 to C4 was observed when the C4 alcohols were treated with SOCl2/pyridine, giving a 2-chloro-3,8-dioxabicyclo[3.2.1
  • chiral auxiliary 10a, and following a survey of conditions and isolation protocols, a 90% yield was obtained when 10a was heated in the presence of 2 equivalents of SOCl2 and 5 equivalents of pyridine in DCE. Flash chromatography of the chloroalkyl ether 11a resulted in significant loss due to hydrolysis
  • groups were small, and attempts to prevent the formation of 13d by slow addition of alcohol 10d to a solution of SOCl2/pyridine in DCE reduced the yield of 11d to 14%. Heating sulfite 13d with tetrabutylammonium chloride led only to hydrolysis back to 10d without rearrangement, indicating that these
PDF
Album
Supp Info
Full Research Paper
Published 16 Apr 2024

Synthesis and characterization of water-soluble C60–peptide conjugates

  • Yue Ma,
  • Lorenzo Persi and
  • Yoko Yamakoshi

Beilstein J. Org. Chem. 2024, 20, 777–786, doi:10.3762/bjoc.20.71

Graphical Abstract
  • (highlighted by purple arrows). A similar situation was observed in the expanded spectrum of 5b (Figure 6b, middle, measured in pyridine). This phenomenon suggests a symmetry break in the carbon cage moiety of the C60–peptide conjugate upon the addition of chiral peptide anchors to the C60 core. Together with
  • crude sample of 5b, with the penta-Glu impurity being soluble in pyridine-d5 (Figures S13–S17, Supporting Information File 1). a) X-band ESR spectra of the 4-oxo-TEMP adduct with 1O2 generated by C60–oligo-Lys (5a) and rose bengal (RB), respectively, in aqueous solutions under irradiation with a green
PDF
Album
Supp Info
Full Research Paper
Published 12 Apr 2024

SOMOphilic alkyne vs radical-polar crossover approaches: The full story of the azido-alkynylation of alkenes

  • Julien Borrel and
  • Jerome Waser

Beilstein J. Org. Chem. 2024, 20, 701–713, doi:10.3762/bjoc.20.64

Graphical Abstract
  • with potential for further modification by cross-coupling. The full scope of the transformation can be found in Supporting Information File 1, Schemes S2 and S3 [45]. Concerning scope limitations, the azido-alkynylation of vinyl-pyridine 1b was unsuccessful and thiazole 1c only afforded 18% of the
  • . Pyridine-substituted alkynyl-BF3K 5b could not be transferred, and only traces of the product were observed. When 5c derived from mestranol was involved in the reaction, the corresponding homopropargylic azide was obtained in <23% yield. We noticed that this particular alkynyltrifluoroborate salt has a low
PDF
Album
Supp Info
Commentary
Published 03 Apr 2024

Evaluation of the enantioselectivity of new chiral ligands based on imidazolidin-4-one derivatives

  • Jan Bartáček,
  • Karel Chlumský,
  • Jan Mrkvička,
  • Lucie Paloušová,
  • Miloš Sedlák and
  • Pavel Drabina

Beilstein J. Org. Chem. 2024, 20, 684–691, doi:10.3762/bjoc.20.62

Graphical Abstract
  • to synthesise ligands featuring two chiral imidazolidin-4-one units linked to the pyridine ring at the 2- and 6- positions (Figure 1 – ligands I and II). These newly designed ligands represent tridentate entities. Such structure modification provides the ligands structurally conformable to well-known
  • tridentate chiral ligands: PyBOX [15] and PyBidine [16]. Additionally, we explored further modifications by substituting the pyridine moiety with an imidazole ring in ligand III (Figure 1), motivated by DFT calculations (see Supporting Information File 1, part S4) which confirmed that imidazole has a similar
  • donor ability to pyridine. This change reduces the ring size within the ligand structure, potentially increasing the space available for coordinating reacting species, thereby possibly enhancing catalytic activity and enantioselectivity. We also aimed to assess the impact of alkyl groups at the 5
PDF
Album
Supp Info
Full Research Paper
Published 02 Apr 2024

HPW-Catalyzed environmentally benign approach to imidazo[1,2-a]pyridines

  • Luan A. Martinho and
  • Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2024, 20, 628–637, doi:10.3762/bjoc.20.55

Graphical Abstract
  • Luan A. Martinho Carlos Kleber Z. Andrade Instituto de Química, Laboratório de Química Metodológica e Orgânica Sintética (LaQMOS), Universidade de Brasília, 70904-970, Brasília, DF, Brazil 10.3762/bjoc.20.55 Abstract The imidazo[1,2-a]pyridine moiety is present in drugs with several biological
  • existing ones. Keywords: GBB-3CR; imidazo[1,2-a]pyridine; microwave; phosphotungstic acid; Introduction Imidazo[1,2-a]pyridine is a privileged structure that plays an important role in organic synthesis and in the pharmaceutical industry. This scaffold is present in drugs with several biological
  • (insomnia). Some recent synthetic approaches to imidazo[1,2-a]pyridine scaffolds include synthetic pathways of transition metal-catalyzed reactions [14], cyclization [15], condensation [16], heteroannular [17], and photocatalytic reactions [18]. These approaches usually involve non-trivial reaction
PDF
Album
Supp Info
Full Research Paper
Published 19 Mar 2024

Synthesis of photo- and ionochromic N-acylated 2-(aminomethylene)benzo[b]thiophene-3(2Н)-ones with a terminal phenanthroline group

  • Vladimir P. Rybalkin,
  • Sofiya Yu. Zmeeva,
  • Lidiya L. Popova,
  • Irina V. Dubonosova,
  • Olga Yu. Karlutova,
  • Oleg P. Demidov,
  • Alexander D. Dubonosov and
  • Vladimir A. Bren

Beilstein J. Org. Chem. 2024, 20, 552–560, doi:10.3762/bjoc.20.47

Graphical Abstract
  • distance 3.6153(10) Å (shift 1.6063(18) Å, twist and fold angles 0.0°). The closest contact in the phenanthroline fragment (blue plane–blue plane, top fragment in Figure 4) had a plane centroid–plane centroid distance of 3.5398(9) Å (shift 0.4273(18) Å, twist and fold angles 0.00°). One pyridine cycle of
PDF
Album
Supp Info
Full Research Paper
Published 11 Mar 2024

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

  • Jens Frackenpohl,
  • David M. Barber,
  • Guido Bojack,
  • Birgit Bollenbach-Wahl,
  • Ralf Braun,
  • Rahel Getachew,
  • Sabine Hohmann,
  • Kwang-Yoon Ko,
  • Karoline Kurowski,
  • Bernd Laber,
  • Rebecca L. Mattison,
  • Thomas Müller,
  • Anna M. Reingruber,
  • Dirk Schmutzler and
  • Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

Graphical Abstract
  • , Bayer AG, Industriepark Höchst, 65926 Frankfurt am Main, Germany 10.3762/bjoc.20.46 Abstract The present work covers novel herbicidal lead structures that contain a 2,3-dihydro[1,3]thiazolo[4,5-b]pyridine scaffold as structural key feature carrying a substituted phenyl side chain. These new compounds
  • -dihydro[1,3]thiazolo[4,5-b]pyridine; acyl-ACP thioesterase; bioisostere; herbicide; heterocycle; Introduction The presence of weed infestations exerts a high strain on food production around the globe by depleting resources for the crops and facilitating the transmission of diseases [1]. Although
  • lead structure with ample space for structural variations. By formally replacing one pyridine moiety of 1,8-naphthyridine 4 by a five-membered thiazole unit, we have identified thiazolo[4,5-b]pyridine 5 as a strong inhibitor of acyl-ACP thioesterase, which has further been confirmed via an X-ray co
PDF
Album
Supp Info
Full Research Paper
Published 01 Mar 2024

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
  • mainly driven by intramolecular hydrogen bonds. The methoxyphenyl-pyridine-methoxyphenyl moiety, developed by Petitjean et al. [19], demonstrates conformational switching upon the addition of acid in aqueous media (Figure 2). The neutral tweezers adopt a "U"-shaped conformation with both arms pointing in
  • attached functional arms. The formation of new hydrogen bonds between -OMe groups and protonated pyridine stabilizes a "W"-shaped open conformation. The conformation switch can be easily followed by NMR spectroscopy in solution. Remarkably, the water-soluble tweezers 1, when functionalized with hydrophobic
  • signals in the low-range visible/NIR region. Upon protonation of the pyridine, the conformation switch leads to a spatial separation of the active Pt moieties and a release of the guest (Figure 4). Also, the same group demonstrated the induction of chirality and fluorescence with chiral guest molecules
PDF
Album
Review
Published 01 Mar 2024

Mono or double Pd-catalyzed C–H bond functionalization for the annulative π-extension of 1,8-dibromonaphthalene: a one pot access to fluoranthene derivatives

  • Nahed Ketata,
  • Linhao Liu,
  • Ridha Ben Salem and
  • Henri Doucet

Beilstein J. Org. Chem. 2024, 20, 427–435, doi:10.3762/bjoc.20.37

Graphical Abstract
  • obtained in 61% and 73% yield, respectively. Finally, the reactivity of pyridinylboronic acids for the preparation of acenaphtho[1,2-c]pyridine (27) was evaluated. The target product 27 was obtained in 53% yield from pyridin-4-ylboronic acid, while no product 27 was obtained from pyridin-3-ylboronic acid
PDF
Album
Supp Info
Full Research Paper
Published 23 Feb 2024

Mechanisms for radical reactions initiating from N-hydroxyphthalimide esters

  • Carlos R. Azpilcueta-Nicolas and
  • Jean-Philip Lumb

Beilstein J. Org. Chem. 2024, 20, 346–378, doi:10.3762/bjoc.20.35

Graphical Abstract
  • photochemical instability, as evidenced by their low N–O bond dissociation energy (BDE ≈ 42 kcal/mol) [28], the reliance on toxic tin hydrides as reductants and the undesired radical recombination with reactive 2-pyridylthiyl radicals that leads to (alkylthio)pyridine byproducts [26]. More recently, N
  • 65. Addition of radical 64 to enyne 62 followed by 6-exo-dig cyclization yields radical intermediate 66. Finally, species 65 acts as a hydrogen atom donor, delivering product 63 while forming pyridine 67 as a byproduct. A similar mechanism would in principle account for EDA-complex-mediated Giese
  • , wherein the activation of complex 74 takes place through SET under constant current electrolysis [64]. The Glorius and Y. Fu groups have independently proposed the formation of analogous charge-transfer complexes involving NHPI esters, bis(pinacolato)diboron (B2pin2), and Lewis bases (pyridine or
PDF
Album
Perspective
Published 21 Feb 2024

Facile approach to N,O,S-heteropentacycles via condensation of sterically crowded 3H-phenoxazin-3-one with ortho-substituted anilines

  • Eugeny Ivakhnenko,
  • Vasily Malay,
  • Pavel Knyazev,
  • Nikita Merezhko,
  • Nadezhda Makarova,
  • Oleg Demidov,
  • Gennady Borodkin,
  • Andrey Starikov and
  • Vladimir Minkin

Beilstein J. Org. Chem. 2024, 20, 336–345, doi:10.3762/bjoc.20.34

Graphical Abstract
  • unambiguously established based on COSY, HSQC, and HMBC NMR-spectroscopic data. Further, the 15N NMR spectrum of 5a confirmed the typical pyrrole-like character of the N(12) atom as well as the pyridine-like character of the N(7) and N(14) atoms (Figure S31, Supporting Information File 1) [21][22]. The
PDF
Album
Supp Info
Full Research Paper
Published 21 Feb 2024

Nucleophilic functionalization of thianthrenium salts under basic conditions

  • Xinting Fan,
  • Duo Zhang,
  • Xiangchuan Xiu,
  • Bin Xu,
  • Yu Yuan,
  • Feng Chen and
  • Pan Gao

Beilstein J. Org. Chem. 2024, 20, 257–263, doi:10.3762/bjoc.20.26

Graphical Abstract
  • reaction system, yielding product 3ak in good yield. Furthermore, heteroaromatic rings, such as pyridine (2l), thiophene (2m), benzoxazole (2n), and benzimidazole (2o) all afforded the desired products (3al–ao) in satisfactory yields. Subsequently, we investigated the substrate scope of amines, which is
PDF
Album
Supp Info
Full Research Paper
Published 08 Feb 2024

Substitution reactions in the acenaphthene analog of quino[7,8-h]quinoline and an unusual synthesis of the corresponding acenaphthylenes by tele-elimination

  • Ekaterina V. Kolupaeva,
  • Narek A. Dzhangiryan,
  • Alexander F. Pozharskii,
  • Oleg P. Demidov and
  • Valery A. Ozeryanskii

Beilstein J. Org. Chem. 2024, 20, 243–253, doi:10.3762/bjoc.20.24

Graphical Abstract
  • studied for the first time. In addition to the pronounced tendency of the title compound to form associates with an intramolecular hydrogen bond of the NHN type (new examples with the participation of pyridine rings, including self-associates are shown) and its inertness to amination reactions of the
  • pyridine rings, the naphthalene core at positions 5(8) and the CH2CH2 bridge (dehydrogenation) undergo chemical modifications under mild conditions, giving the corresponding acenaphthylenes. The latter can also be obtained in an unusual way by tele-elimination from 5,8-dibromodipyridoacenaphthene by
  • , despite the presence of two pyridine nitrogen atoms, is extremely inert towards nucleophilic and oxidative amination reactions. Although molecule 5 does not explicitly contain deactivating electron-donating substituents such as alkoxy and dialkylamino (except for alkyl groups), the observed inertness may
PDF
Album
Supp Info
Full Research Paper
Published 08 Feb 2024

Photochromic derivatives of indigo: historical overview of development, challenges and applications

  • Gökhan Kaplan,
  • Zeynel Seferoğlu and
  • Daria V. Berdnikova

Beilstein J. Org. Chem. 2024, 20, 228–242, doi:10.3762/bjoc.20.23

Graphical Abstract
  • irradiation with orange light in several solvents [40]. However, due to the technical limitations of the spectrometer, Pummerer and Marondel were not able to detect the short-living Z-11a in aromatic solvents such as benzene, bromobenzene and pyridine. Nevertheless, the E–Z isomerization of 11a was observed
PDF
Album
Review
Published 07 Feb 2024

Optimizations of lipid II synthesis: an essential glycolipid precursor in bacterial cell wall synthesis and a validated antibiotic target

  • Milandip Karak,
  • Cian R. Cloonan,
  • Brad R. Baker,
  • Rachel V. K. Cochrane and
  • Stephen A. Cochrane

Beilstein J. Org. Chem. 2024, 20, 220–227, doi:10.3762/bjoc.20.22

Graphical Abstract
  • . Finally, the benzyl-protecting groups in compound 7 were cleaved via hydrogenolysis, followed by co-evaporation of the resulting crude product in pyridine. This yielded a monopyridyl salt, setting the stage for the final lipid coupling and deprotection sequence. To establish the vital lipid diphosphate
PDF
Album
Supp Info
Full Research Paper
Published 06 Feb 2024

Comparison of glycosyl donors: a supramer approach

  • Anna V. Orlova,
  • Nelly N. Malysheva,
  • Maria V. Panova,
  • Nikita M. Podvalnyy,
  • Michael G. Medvedev and
  • Leonid O. Kononov

Beilstein J. Org. Chem. 2024, 20, 181–192, doi:10.3762/bjoc.20.18

Graphical Abstract
  • overnight, then quenched by addition of dry ice (solid CO2) and concentrated under reduced pressure. The residue was co-concentrated with toluene (3 mL), dried in vacuo, dissolved in anhydrous pyridine (3 mL per 0.1 mmol of sialyl donor), and acetic anhydride (3 mL per 0.1 mmol of sialyl donor) was added
PDF
Album
Supp Info
Full Research Paper
Published 31 Jan 2024

Photoinduced in situ generation of DNA-targeting ligands: DNA-binding and DNA-photodamaging properties of benzo[c]quinolizinium ions

  • Julika Schlosser,
  • Olga Fedorova,
  • Yuri Fedorov and
  • Heiko Ihmels

Beilstein J. Org. Chem. 2024, 20, 101–117, doi:10.3762/bjoc.20.11

Graphical Abstract
  • [c]quinolizinium tetrafluoroborate (3g) According to GP, a solution (c = 0.25 mM) of (E)-5-acetylamino-2-(3,4-dimethoxystyryl)pyridine (30.0 mg, 101 µmol) in a mixture of MeCN/H2O (7:3, 400 mL) was irradiated for 33 min and the crude product was washed with n-hexane (3 mL) and redissolved in dest
  • : piperidine, MeOH, reflux (2a,c), ii: Ca(OTf)2, Bu4NPF6, 130 °C (2d,f), iii: N2H4·H2O, Pd/C, MeOH, reflux (2b), iv: NaNO2, CuCl, aq HCl (37%), room temp., 2 h, 60 °C, 30 min (2e), v: acetyl chloride, pyridine, THF, room temp. (2g). Photoinduced formation of styrylpyridine derivatives 2b–g to the benzo[c
PDF
Album
Supp Info
Full Research Paper
Published 18 Jan 2024

Beyond n-dopants for organic semiconductors: use of bibenzo[d]imidazoles in UV-promoted dehalogenation reactions of organic halides

  • Kan Tang,
  • Megan R. Brown,
  • Chad Risko,
  • Melissa K. Gish,
  • Garry Rumbles,
  • Phuc H. Pham,
  • Oana R. Luca,
  • Stephen Barlow and
  • Seth R. Marder

Beilstein J. Org. Chem. 2023, 19, 1912–1922, doi:10.3762/bjoc.19.142

Graphical Abstract
  • -containing catalysts [32]. We note that another all-organic reductive dimerization of benzyl halides using 2,3,5,6-tetrakis(tetramethylguanidino)pyridine has recently been reported [37]. The less readily reduced halides examined here (1d,e, and 2) are only sluggishly converted, even when using both (N-DMBI)2
PDF
Album
Supp Info
Full Research Paper
Published 14 Dec 2023

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

  • Karolis Leitonas,
  • Brigita Vigante,
  • Dmytro Volyniuk,
  • Audrius Bucinskas,
  • Pavels Dimitrijevs,
  • Sindija Lapcinska,
  • Pavel Arsenyan and
  • Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

Graphical Abstract
  • Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia 10.3762/bjoc.19.139 Abstract The pyridine-3,5-dicarbonitrile moiety has gained significant attention in the field of materials chemistry, particularly in the development of heavy-metal-free pure organic light-emitting diodes (OLEDs). Extensive
  • research on organic compounds exhibiting thermally activated delayed fluorescence (TADF) has led to numerous patents and research articles. This study focuses on the synthesis and investigation of the semiconducting properties of polyaromatic π-systems containing two and three fragments of pyridine-2,6
  • compounds. In general, polyaromatic π-systems with pyridine-3,5-dicarbonitrile fragments demonstrate promising potential for use in organic electronic devices, such as OLEDs. Keywords: charge transport; intramolecular charge transfer; photophysical properties; pyridine-3,5-dicarbonitrile; Introduction The
PDF
Album
Supp Info
Full Research Paper
Published 12 Dec 2023

Controlling the reactivity of La@C82 by reduction: reaction of the La@C82 anion with alkyl halide with high regioselectivity

  • Yutaka Maeda,
  • Saeka Akita,
  • Mitsuaki Suzuki,
  • Michio Yamada,
  • Takeshi Akasaka,
  • Kaoru Kobayashi and
  • Shigeru Nagase

Beilstein J. Org. Chem. 2023, 19, 1858–1866, doi:10.3762/bjoc.19.138

Graphical Abstract
  • reduction [21] using a degassed tetrabutylammonium hexafluorophosphate (TBAF) pyridine solution. After stirring for 3 h, a dark green solution was obtained. CS2 was added to precipitate TBAF, and the solution was filtered to collect the La@C2v-C82 anion solution. The solvent was then removed under reduced
  • in the second step. Preparation of the La@C2v-C82 anion As described in [21], La@C2v-C82 (0.34 × 10−6 mol) was dissolved in 10 mL of a pyridine solution containing TBAF (0.54 × 10−3 mol) and then stirred for 2 h under an Ar atmosphere. The resulting green solution was concentrated to 2.0 mL. CS2 was
PDF
Album
Supp Info
Full Research Paper
Published 11 Dec 2023

Active-metal template clipping synthesis of novel [2]rotaxanes

  • Cătălin C. Anghel,
  • Teodor A. Cucuiet,
  • Niculina D. Hădade and
  • Ion Grosu

Beilstein J. Org. Chem. 2023, 19, 1776–1784, doi:10.3762/bjoc.19.130

Graphical Abstract
  • (Figure 2) were designed to be obtained from precursors containing two 1,4-dioxobenzene fragments required to facilitate π–π interactions with the pyridine unit in the axle (compound 6 in Scheme 1) and confer stability to the supramolecular complex necessary for the formation of [2]rotaxanes. For the
  • synthesis of the axle unit (compound 6 in Scheme 1) we considered a convergent synthetic approach that consist in preparation of the stopper, functionalized with azide groups, decoration of the central pyridine-based moiety with propargyl groups and their connection by CuAAC click chemistry. Thus, as
  • -functonalized stopper 3 after substitution of bromine with azide. The dialkyne-decorated pyridine 5 was prepared starting from 2,6-bis(bromomethyl)pyridine that was reacted with compound 4, under phase transfer catalysis (Scheme 1). Finally, the axle 6, as well as the reference macrocycles M1 and M2 [44], were
PDF
Album
Supp Info
Full Research Paper
Published 20 Nov 2023

Selectivity control towards CO versus H2 for photo-driven CO2 reduction with a novel Co(II) catalyst

  • Lisa-Lou Gracia,
  • Philip Henkel,
  • Olaf Fuhr and
  • Claudia Bizzarri

Beilstein J. Org. Chem. 2023, 19, 1766–1775, doi:10.3762/bjoc.19.129

Graphical Abstract
  • (BzQuTr) [42] and the cobalt precursor Co(NCS)2(py)4 [43], where py is pyridine. The reaction was performed under an argon atmosphere at room temperature. The resulting complex 1 was obtained after evaporation of the solvent, as a lilac precipitate in good yield (60%). The structure was investigated by
  • (NCS)2(NN) complexes, where NN is a chelating diimine compound such as pyridyl-tetrazole [44], or a pyridine-oxazole [45]. The bond lengths are very similar when comparing the polymorphs 1a and 1b. Nevertheless, the bond angles vary significantly (see Table S2 in Supporting Information File 1
PDF
Album
Supp Info
Full Research Paper
Published 17 Nov 2023

Unprecedented synthesis of a 14-membered hexaazamacrocycle

  • Anastasia A. Fesenko and
  • Anatoly D. Shutalev

Beilstein J. Org. Chem. 2023, 19, 1728–1740, doi:10.3762/bjoc.19.126

Graphical Abstract
  • ). Next, we tested other protic (iPrOH, MeOH, EtOH/H2O, 1,4-dioxane/H2O) and aprotic (THF, 1,4-dioxane, pyridine, MeCN) solvents for the dimerization of 8 promoted by hydrazine hydrate to improve both yield and purity of 5 (Table 1, entries 4‒17). As can be seen from Table 1 the solvent had a dramatic
  • effect on the outcome of the reaction. With THF, pyridine, MeCN, iPrOH, EtOH/H2O, or 1,4-dioxane/H2O either low conversion of 8 (Table 1, entry 4), or poor product yield (entries 9, 10, 12, 16, and 17), or low purity of 5 (entries 11 and 12) were observed. Using 1,4-dioxane with 3 equivalents of N2H4·H2O
PDF
Album
Supp Info
Full Research Paper
Published 15 Nov 2023

Tying a knot between crown ethers and porphyrins

  • Maksym Matviyishyn and
  • Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

Graphical Abstract
  • macrocycles. The formation of (29b)2-Hg was reversible – its reaction with [2.2.2]cryptand resulted in the removal of mercury(II) and the contraction to 29b. Recently, Sessler and co-workers synthesised a new macrocycle 36 exploiting a pyridine-bridged dipyrroledialdehyde 35 (Scheme 10) [131]. The compound
  • also demonstrated the crowned fused expanded porphyrinoids incorporating a pyridine moiety [135]. Macrocycles 45 were obtained in 5–10% yield from the condensation of 38 with the corresponding pyridine-based dipyrromethane analogue. Compound 45 exhibited a unique structural arrangement, with the
  • pyridine ring and two thiophenes inverted and fused with two pyrrole nitrogen atoms. The macrocycles exhibited facile oxidations, indicating their electron-rich nature, and demonstrated selective sensing of Cu2+ ions. Conclusion and Outlook The construction of new macrocycles has been a driving force for
PDF
Album
Perspective
Published 27 Oct 2023
Other Beilstein-Institut Open Science Activities