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(E,Z)-1,1,1,4,4,4-Hexafluorobut-2-enes: hydrofluoroolefins halogenation/dehydrohalogenation cascade to reach new fluorinated allene
Abstract A series of 2,3-dihalo-1,1,1,4,4,4-hexafluorobutanes and 2-halo-1,1,1,4,4,4-hexafluorobut-2-enes were prepared from commercially available hydrofluoroolefins 1,1,1,4,4,4-hexafluorobut-2-enes and their 1H, 19F and 13C chemical shifts measured. Some reactions of synthesized 2-halo-1,1,1,4,4,4-hexafluorobut-2-enes have been investigated. A simple, one-pot procedure for the preparation of a new allene (1,1,4,4,4-pentafluorobuta-1,2-diene) and some of its transformations is presented. Beilstein J. Org. Chem. 2024, 20, 452–459. doi:10.3762/bjoc.20.40 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - February 27, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: allenes dehydrohalogenation 1,1,1,4,4,4-hexafluorobut-2-enes isomerization Full Research Paper Source Type: research

Development of a chemical scaffold for inhibiting nonribosomal peptide synthetases in live bacterial cells
In this study, we investigated the influence of a modification of 2′-OH in the AMS scaffold with different functional groups on binding to target enzymes and bacterial cell penetration. The inhibitor 7 with a cyanomethyl group at 2′-OH showed desirable inhibitory activity against both recombinant and intracellular gramicidin S synthetase A (GrsA) in the gramicidin S-producer Aneurinibacillus migulanus ATCC 9999, providing an alternative scaffold to develop novel A-domain inhibitors. Beilstein J. Org. Chem. 2024, 20, 445–451. doi:10.3762/bjoc.20.39 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - February 26, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: adenylation domain inhibitor gramicidin S synthetase natural product nonribosomal peptide nonribosomal peptide synthetase Full Research Paper Source Type: research

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
Abstract The Pd-catalyzed annulative π-extension of 1,8-dibromonaphthalene for the preparation of fluoranthenes in a single operation has been investigated. With specific arenes such as fluorobenzenes, the Pd-catalyzed double functionalization of C–H bonds yields the desired fluoranthenes. The reaction proceeds via a palladium-catalyzed direct intermolecular arylation, followed by a direct intramolecular arylation step. As the C–H bond activation of several benzene derivatives remains very challenging, the preparation of fluoranthenes from 1,8-dibromonaphthalene via Suzuki coupling followed by intramolecul...
Source: Beilstein Journal of Organic Chemistry - February 23, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: catalysis – H bond functionalization direct arylation fluoranthenes palladium Full Research Paper Source Type: research

Enhanced host – guest interaction between [10]cycloparaphenylene ([10]CPP) and [5]CPP by cationic charges
Abstract A dication of [5]cycloparaphenylene ([5]CPP2+) was selectively encapsulated by neutral [10]CPP to form the shortest double-layer carbon nanotube, [10]CPP⊃[5]CPP2+. While the same host–guest complex consisted of neutral CPPs, [10]CPP⊃[5]CPP, was already reported, the cationic complex showed an about 20 times higher association constant in (CDCl2)2 at 25 °C (103 mol L−1). Electrochemical and photophysical analyses and theoretical calculations suggested the partial electron transfer from [10]CPP to [5]CPP2+ in the complex, and this charge-transfer (CT) interaction is most likely the origi...
Source: Beilstein Journal of Organic Chemistry - February 23, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: charge-transfer cycloparaphenylene dication host – guest chemistry Letter Source Type: research

Green and sustainable approaches for the Friedel – Crafts reaction between aldehydes and indoles
Abstract The synthesis of indoles and their derivatives, more specifically bis(indolyl)methanes (BIMs), has been an area of great interest in organic chemistry, since these compounds exhibit a range of interesting biological and pharmacological properties. BIMs are naturally found in cruciferous vegetables and have been shown to be effective antifungal, antibacterial, anti-inflammatory, and even anticancer agents. Traditionally, the synthesis of BIMs has been achieved upon the acidic condensation of an aldehyde with indole, utilizing a variety of protic or Lewis acids. However, due to the increased environmental awareness ...
Source: Beilstein Journal of Organic Chemistry - February 22, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: aldehyde BIMs Friedel – Crafts reaction green chemistry indole Review Source Type: research

Facile approach to N,O,S-heteropentacycles via condensation of sterically crowded 3H-phenoxazin-3-one with ortho-substituted anilines
Abstract A convenient method for the synthesis of a series of 2-(arylamino)-3H-phenoxazin-3-ones based on the nucleophilic substitution reaction between sterically crowded 3H-phenoxazin-3-one and arylamines performed by short-term heating of the melted reactants at 220–250 °C is described, and the compounds were characterized by means of single-crystal X-ray crystallography, NMR, UV–vis, and IR spectroscopy, as well as cyclic voltammetry. The reaction with o-amino-, o-hydroxy-, and o-mercapto-substituted arylamines widened the scope and provided an access to derivatives of N,O- and N,S-heteropentacyclic qu...
Source: Beilstein Journal of Organic Chemistry - February 21, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: 3H-phenoxazin-3-one fluorescence molecular structure pentacyclic heterocycles synthesis Full Research Paper Source Type: research

Mechanisms for radical reactions initiating from N-hydroxyphthalimide esters
Abstract Due to their ease of preparation, stability, and diverse reactivity, N-hydroxyphthalimide (NHPI) esters have found many applications as radical precursors. Mechanistically, NHPI esters undergo a reductive decarboxylative fragmentation to provide a substrate radical capable of engaging in diverse transformations. Their reduction via single-electron transfer (SET) can occur under thermal, photochemical, or electrochemical conditions and can be influenced by a number of factors, including the nature of the electron donor, the use of Brønsted and Lewis acids, and the possibility of forming charge-transfer complex...
Source: Beilstein Journal of Organic Chemistry - February 21, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: decarboxylative couplings mechanisms NHPI-esters radical reactions Perspective Source Type: research

Spatial arrangements of cyclodextrin host – guest complexes in solution studied by 13C NMR and molecular modelling
Abstract 13C NMR spectroscopic analyses of Cs symmetric guest molecules in the cyclodextrin host cavity, combined with molecular modelling and solid-state X-ray analysis, provides a detailed description of the spatial arrangement of cyclodextrin host–guest complexes in solution. The chiral cavity of the cyclodextrin molecule creates an anisotropic environment for the guest molecule resulting in a splitting of its prochiral carbon signals in 13C NMR spectra. This signal split can be correlated to the distance of the guest atoms from the wall of the host cavity and to the spatial separation of binding sites preferred b...
Source: Beilstein Journal of Organic Chemistry - February 20, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: anisotropy 13C NMR cyclodextrin host – guest complexes Full Research Paper Source Type: research

Elucidating the glycan-binding specificity and structure of Cucumis melo agglutinin, a new R-type lectin
Abstract Plant lectins have garnered attention for their roles as laboratory probes and potential therapeutics. Here, we report the discovery and characterization of Cucumis melo agglutinin (CMA1), a new R-type lectin from melon. Our findings reveal CMA1’s unique glycan-binding profile, mechanistically explained by its 3D structure, augmenting our understanding of R-type lectins. We expressed CMA1 recombinantly and assessed its binding specificity using multiple glycan arrays, covering 1,046 unique sequences. This resulted in a complex binding profile, strongly preferring C2-substituted, beta-linked galactose (both G...
Source: Beilstein Journal of Organic Chemistry - February 19, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: carbohydrate glycan array melon plant lectin R-type Full Research Paper Source Type: research

Discovery of unguisin J, a new cyclic peptide from Aspergillus heteromorphus CBS 117.55, and phylogeny-based bioinformatic analysis of UngA NRPS domains
In this study, a new GABA-containing heptapeptide – unguisin J (1) – along with known unguisin B (2) were isolated from a solid culture of Aspergillus heteromorphus CBS 117.55. The structure of compound 1 was elucidated by extensive 1D and 2D NMR spectroscopic analysis including HSQC, HMBC, COSY, and 2D NOESY as well as HRESIMS. The stereochemistry of 1 and 2 was determined by Marfey’s method. A biosynthetic gene cluster (BGC) encoding unguisins B and J was compared to characterized BGCs in other Aspergillus sp. Since the unguisin family of heptapetides incorporate different amino acid residues at differe...
Source: Beilstein Journal of Organic Chemistry - February 19, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: adenylation domain condensation domain fungal non-ribosomal peptide synthetase heptapeptide unguisin biosynthesis Full Research Paper Source Type: research

Synthesis of π -conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments
Abstract The “precursor approach” has proved particularly valuable for the preparation of insoluble and unstable π-conjugated polycyclic compounds (π-CPCs), which cannot be synthesized via in-solution organic chemistry, for their improved processing, as well as for their electronic investigation both at the material and single-molecule scales. This method relies on the synthesis and processing of soluble and stable direct precursors of the target π-CPCs, followed by their final conversion in situ, triggered by thermal activation, photoirradiation or redox control. Beside well-established reaction...
Source: Beilstein Journal of Organic Chemistry - February 15, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: arenes chalcogens extrusion fused-ring systems precursor approach Review Source Type: research

Synthesis of spiropyridazine-benzosultams by the [4 + 2] annulation reaction of 3-substituted benzoisothiazole 1,1-dioxides with 1,2-diaza-1,3-dienes
Abstract A simple and efficient method for the synthesis of spiropyridazine-benzosultams has been developed by means of [4 + 2] annulation reaction of 3-substituted benzoisothiazole 1,1-dioxides with 1,2-diaza-1,3-dienes. This approach displays advantages such as mild reaction conditions, wide substrate range tolerance, simple operation, compatibility with gram-scale preparation. Beilstein J. Org. Chem. 2024, 20, 280–286. doi:10.3762/bjoc.20.29 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - February 14, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: [4 2] annulation reaction 1,2-diaza-1,3-dienes spiro-benzosultams 3-substituted benzoisothiazole 1,1-dioxides Full Research Paper Source Type: research

Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 production
In this study, we investigate the regioselectivity of the rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions between diynes and C70 as a novel procedure for generating C70 bis(fulleroid) derivatives. The aim is to shed light on the regioselectivity of the process through both experimental and computational approaches. In addition, the photooxidation of one of the C–C double bonds in the synthesized bis(fulleroids) affords open-cage C70 derivatives having a 12-membered ring opening. Beilstein J. Org. Chem. 2024, 20, 272–279. doi:10.3762/bjoc.20.28 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - February 13, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: cycloadditions DFT calculations [70]fullerene open-cage fullerenes rhodium Full Research Paper Source Type: research

Additive-controlled chemoselective inter-/intramolecular hydroamination via electrochemical PCET process
Abstract Electrochemically generated amidyl radical species produced distinct inter- or intramolecular hydroamination reaction products via a proton-coupled electron transfer (PCET) mechanism. Cyclic voltammetry (CV) analysis indicated that the chemoselectivity was derived from the size of the hydrogen bond complex, which consisted of the carbamate substrate and phosphate base, and could be controlled using 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as an additive. These results provide fundamental insights for the design of PCET-based redox reaction systems under electrochemical conditions. Beilstein J. Org. Chem. 2024, 20...
Source: Beilstein Journal of Organic Chemistry - February 12, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: amidyl radical cyclic voltammetry electrosynthesis hydroamination proton coupled electron transfer Full Research Paper Source Type: research

Substitution reactions in the acenaphthene analog of quino[7,8-h]quinoline and an unusual synthesis of the corresponding acenaphthylenes by tele-elimination
Abstract The possibility of functionalization of dipyrido[3,2-e:2′,3′-h]acenaphthene containing a quino[7,8-h]quinoline fragment and being a highly basic diazine analog of 1,8-bis(dimethylamino)naphthalene (“proton sponge”) has been 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 b...
Source: Beilstein Journal of Organic Chemistry - February 8, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: dipyrido[3,2-e:2 ′ ,3 -h]acenaphthene (acenaphthylene) hydrogen bonding π -stacking substitution reactions tele-elimination Full Research Paper Source Type: research